The Captain's Annex

$797.50 - $2,777.50 Nightly
Unit Type: House
Pets Allowed: Pets Allowed
Address: 719 Eisenhower Drive #1 Key West, FL 33040
Neighborhood: Old Town
Stay Type: Nightly, Weekly, Monthly

Overview Read Reviews


"Great property in Key West! Our extended family of 8 people stayed here for one week. We called Shel when we were just outside of Key West. He was waiting for us when we arrived at the house. He showed us everything we needed to know and also personally met us at check out to obtain any feedback about the property.. The house was three levels. It was very spacious for our group. Very impressed that the air conditioning was just as good on the third floor as it was on the first floor. Bikes are the easiest way to get to town as the ride is flat and short. Only need one car to get groceries to cook in several nights. Very impressed with Last Key Realty as Shel and the other members of the team provided excellent communication during the entire rental process. We rented numerous houses in the past and they were the most professional and customer friendly. Highly recommend this house!" -Barbara B. 07/15


If you long for the ideal Key West vacation home with spacious and upscale interiors, a private pool, an Old Town location and water access to enjoy one of the best features of Key West (The Water!) then you have found your match. "The Captain's Annex" meets all of these important criteria and more. In the small community of Paradise Harbor, you'll have the perfect setting to enjoy the ultimate Key West vacation with plenty of space to stretch out in your own accommodations when it's time to escape. Whether you're cooling off inside this luxury home, relaxing by your private pool, or heading out on the beautiful waters of Key West from your private boat slip, you'll find you have everything you need and more at "The Captain's Annex."


The unique location of this home is the best of all things Key West: right on the water at Garrison Bight with a private dock and boat slip, in Old Town off Eaton St close to the Historic Seaport restaurants and shops and just a short walk from Duval Street and the White Street galleries. All of the typical Key West spots are accessible by a short walk or bike ride, but should you decide to drive there is private off-street parking for two cars with this home. Speaking of parking, this home also includes a private boat slip on the docks near the house.


"The Captain's Annex" has bright, tropical colors, tall ceilings, and luxurious modern furnishings. The living area boasts a large flat screen HDTV with DVD player, which you can watch from the comfort of the plush living room furniture or the kitchen/dining areas thanks to the open living plan of this main floor. The living room sofa also pulls out to a queen-sized bed for extra guests. The kitchen is fully equipped with state-of-the-art appliances and all of the tools and utensils you will need to prepare a meal at home. The dining area has seating for 8 with 4 additional seats at the kitchen bar. There is also an iPod dock in the living area to play some music while everyone gathers on the main floor.


Through the sliding glass doors of the living area is one of the highlights of this home: the private back yard complete with a large deck and a private pool. Fully fenced for privacy and surrounded by lush tropical greenery, this will undoubtedly be a primary gathering place for your group. There are chaise lounges by the heat-optional pool when it's time for a swim and some sun. A full outdoor dining set by the pool can comfortably seat 6. The backyard is complete with a propane grill for an outdoor BBQ by the pool. Cross the parking lot of this private complex to the docks where you will find your own boat slip!


This home is an ideal layout for comfort and space for a group. The master bedroom is on the second level and has a king-sized bed, a large flat-screen TV, plenty of dresser space, and a private balcony overlooking the water. The master bathroom is en-suite with dual sinks, a large soaking tub, a glass and marble shower and a huge walk-in closet. The second bedroom is also on the second living level, and has a queen sized bed, a flat-screen TV and a private balcony. The second bathroom is also en-suite and has a tub/shower combo. The third level can sleep a total of 6: there is a private bedroom with two twin beds that can convert to a king upon request, and an open room with another 4 twin beds, which can convert to 2 king sized beds upon request. The third level accommodations share one full bathroom with a tub/shower combo. Additional sleeping area is available in the living room, as the sofa pulls out into a queen bed. There is also a half bath off the living room on the main floor.


Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking, Flat Screen State-of-the Art HD TVs in all bedrooms and main living area, Fully Equipped Chef's Kitchen with Gourmet Appliances, Private Pool with available Pool Heat, Private Boat Slip, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 10-12 adults.


Available Unavailable Check In Check Out
June 2017
Sun Mon Tue Wed Thu Fri Sat
     01 02 03
04 05 06 07 08 09 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30
July 2017
Sun Mon Tue Wed Thu Fri Sat
02 03 04 05 06 07 08
09 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31
August 2017
Sun Mon Tue Wed Thu Fri Sat
   01 02 03 04 05
06 07 08 09 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
September 2017
Sun Mon Tue Wed Thu Fri Sat
      01 02
03 04 05 06 07 08 09
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
October 2017
Sun Mon Tue Wed Thu Fri Sat
01 02 03 04 05 06 07
08 09 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31
November 2017
Sun Mon Tue Wed Thu Fri Sat
    01 02 03 04
05 06 07 08 09 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30
December 2017
Sun Mon Tue Wed Thu Fri Sat
      01 02
03 04 05 06 07 08 09
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
January 2018
Sun Mon Tue Wed Thu Fri Sat
  01 02 03 04 05 06
07 08 09 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
February 2018
Sun Mon Tue Wed Thu Fri Sat
     01 02 03
04 05 06 07 08 09 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28
March 2018
Sun Mon Tue Wed Thu Fri Sat
     01 02 03
04 05 06 07 08 09 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
April 2018
Sun Mon Tue Wed Thu Fri Sat
01 02 03 04 05 06 07
08 09 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
May 2018
Sun Mon Tue Wed Thu Fri Sat
   01 02 03 04 05
06 07 08 09 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31


Map may not be 100% accurate.


  • Area - Old Town
  • Property Type - House
  • Floors - Three Story Home
  • Bedrooms - 4
  • Sleep Cap - 12
  • Rental License Period - Nightly, Weekly, Monthly
  • Pets - Pets Allowed
  • Parking - Off-Street - Designated Space


  • Number of Seperate Beds - 9
  • Bedding Bed 1 - King
  • Balcony Bed 1
  • En Suite Bathroom Bed 1
  • Floor Bed 1 - Second
  • Bedding Bed 2 - Queen
  • Balcony Bed 2
  • En Suite Bathroom Bed 2
  • Floor Bed 2 - Second
  • Bedding Bed 3 - 2 Twins to King Combo
  • Floor Bed 3 - Third
  • Bedding Bed 4 - 4 Twins to King Combo
  • Floor Bed 4 - Third


  • Number of Bathrooms - 3.5
  • Bathroom 1 Size - Full
  • Bathroom 1 Type - Shower & Tub
  • Bathroom 1 En Suite
  • Bathroom 1 Floor - Second
  • Bathroom 2 Size - Full
  • Bathroom 2 Type - Shower/Tub Combo
  • Bathroom 2 En Suite
  • Bathroom 2 Floor - Second
  • Bathroom 3 Size - Full
  • Bathroom 3 Type - Shower/Tub Combo
  • Bathroom 3 Floor - Third
  • Bathroom 4 Size - Half
  • Bathroom 4 Floor - First

Indoor Amenities

  • Sleeper Sofa - Queen
  • Sleeper Sofa Mattress - Standard
  • Washer and Dryer
  • Dining Room Seats - 8

Outdoor Amenities

  • Pool - Private
  • Heated Pool
  • Grill - Propane


  • Living Room TV - HD
  • Living Room DVD - Standard DVD
  • iPod Dock

Recent Reviews About This Property

Great Property, Great Location, Great Time

11 of us stayed 4 nights at the Captains Annex for a Bachelor party and this house couldn't have been any better. When we first got there Shel was there to greet us and give us the run down on all things Key West. All of his recommendations were spot on and it really made it easier to plan out our days there. I would definitely stay here again if traveling back to Key West.

Timothy F, 08/25/2016

Gorgeous spacious house for a large group!

Great location in Key West! Perfect house for a large family gathering! We had a fabulous time in Key West celebrating our daughter's 21st Birthday. The house has everything you could possibly need. The kitchen is gorgeous and we loved the open layout. We spent a lot of time in the pool during the day (August is pretty hot in the keys) :) Shel, the Guest Services Coordinator was fabulous! He was very attentive and quick to make sure we had everything we needed. (We rented bikes, and when they were delivered, he stopped by and noticed that it had just rained and the seats were wet, so he dried them off for us! So sweet!)

We would definitely stay in this house again!


Kathy S, 08/15/2016

Fantastic property and location

This place is great. Modern and huge. We had two families, 9 people total. We were very comfortable. Shel the manager was great. Be sure to have him review the list of restaurants with you. He knows all the local favorites. We will be back.

Robert S, 08/06/2016

Awesome Location & House

We comfortably slept 2 families in this great house and had a wonderful time. Shel gave us plenty of recommendations of where to eat and was a huge help! Thanks for a great trip.

Anonymous , 07/21/2016

Beautiful, well-kept property!

I was very impressed with this property. We comfortably slept a large group of women and there were several bathrooms to accomodate us. Shel welcomed us even though our flight was late and provided a list of recommended restaurants which helped us make decisions much faster. Thoroughly enjoyed our trip to Key West and our experience with Shel at HomeAway.

Sharon B, 07/06/2016

Girlfriend Get away

We had a great time in Key West it was the first time visit for most of us . a few of the ladies had been there. We arrived and Shel met us there and gave us a tour of the house. He told us all the neat places to go and things to do. The house was very clean and beautiful. It was 11 of us and we had a fabulous time. We will returned again


D Jones


Debra J, 07/01/2016

Very nice and clean property.

We enjoyed the property and our visit to Key West.

Marion M, 06/19/2016

Great Place!

Stayed there for 4 days 3 nights. Bigger party for the bachelor party. The place is nice, very big and spacious. Virtually sound proof. We had an issue with the air, Shel was able to send someone out to take look and fix it immediately. Shel is very quick to help out and communicate. Close enough to everything. The swimming pool is more of a hot tub size; so don't expect to swim laps. Kitchen and grill are clutch for big group meals. Would certainly stay there on the next trip down.

Arturo R, 05/27/2016

Response from Last Key Realty:

Thanks for the review! While we normally do not accept 3 night stays OR bachelor parties...this group was a bit of an exception and was luckily a great group of guests! Thanks for taking good care of the house and we are so happy to hear you enjoyed your time in The Captain's Annex. Hopefully we can see you back for your Honeymoon next time :)


Fantastic house, great managers -- amazing!

Highly recommended!! Our group had a fantastic stay at the Captain's Annex. The house itself is very nice, well appointed, very good size for a large group (we had 12 and were quite comfortable), and an excellent + walkable location to anywhere you want to go in Key West. The property manager Shel we worked with was great-- always available if we needed him but not overbearing at all, and provided some excellent local recommendations. I would definitely recommend this property for a family getaway, bachelor/bachelorette party - anything with a big group to have a great/comfy home base in Key West. Would stay here again for sure!!

Adam G, 05/19/2016

Amazing and Perfect

The Captain's Annex is absolutely perfect in every way. Shel and the concierge staff made sure that we had everything we needed and that our stay was as perfect as the wedding we were in town for. Everyone that stayed at the house said the same thing that it was wonderful and that we'd be back again. Great family location away from the Duval action but close enough to enjoy all the fun of old town. Shel could not have been a better person to deal with and everything he did for us was greatly appreciated. Highly recommend this rental to families and couples wanting to relax in paradise.

Mark , 04/20/2016

Exceeded All Expectations. Highly Recommend!

The house was absolutely beautiful, clean, and in a great location. There were plenty of bars and restaurants within a 20 minute walk (or 5 minute cab ride), but the house itself provided a sense of privacy and relaxation. What really sets this house apart is the superior.

Scott S, 04/06/2016


Could not have been better for us. We were able to dock out boat in the back, slept everyone comfortably (and quietly). The kitchen is well stocked, loved the pool. And Shel had the place stocked with our extensive grocery list. He also was able to get us in early. He was informative and on call at all times. It really could not have been a better experience. Thank you!

Rob L, 03/17/2016

This is Paradise

This property is even better then it looks. ( If you can imagine). The home is far larger then we had anticipated. The 4 bathrooms with a large group was amazing. The house is separated onto 3 levels. This keeps the noise controlled between the floors. The washer/dryer was a great feature for us. We came home with zero laundry. Shel the property manager ( who is great), stock the home with groceries. We cooked breakfast and BBQ food the entire stay. The backyard is great to relax, and the pool was nice and warm. We will 100% be back to this property.

Garrett G, 03/10/2016

Amazing property with very convenient boat slip!

The property was exceptionally clean and well-maintained and Shel even met us for a tour, as well as provided us with what turned out to be some of our favorite restaurants of our trip! The brunch at My Blue Heaven was phenomenal, and we also enjoyed relaxing at the pool while grilling out. Additionally, we brought our boat and were able to use the public boat ramp down the street and having our own private boat slip was a real treat! I would absolutely recommend dealing with Last Key Realty and would rent The Captain's Annex again without hesitation! Thanks for the wonderful hospitality and making our stay so pleasant!

Rick C, 03/02/2016

Girlfriends' getaway

Lovely home and we loved all of Shel's restaurant recommendations.

Susan A, 02/24/2016

Great holiday home

We had a great holiday!

The house was great. Shel made sure we had everything we needed!

The only thing I would warn people of is its a bit of a walk from downtown (25-30 mins)

We walked it every day but it was a bit far!


Loralee M, 02/13/2016

Great retreat

Went down for a week-long work trip with six other colleagues.  Plenty of space to stretch out that provided privacy when needed while the great communal areas allowed us to hang out comfortably.

Everything worked as advertised and we didn't have any issues.

Shel, the house manager, met us at the house and made sure we made it our home away from home right away.

Excellent experience.

With two parking spots.


Chun-Wei Y, 01/30/2016

the perfect gem.

This was the perfect spot and we will be renting here again. Shel was very helpful in getting us situated. The House was in great shape and was the perfect size to accommodate our team.  We were here for a sailing event and it was a great retreat at the end of the day. Looking forward to staying here again.

geoffrey e, 01/15/2016

Outstanding Property, Location, and Management

The house was beautiful. Clean, well maintained and very comfortable for our group of 8. We loved the location as it is close enough to downtown to walk or bike but far enough away to be quiet and peaceful in the evenings. Shel, the property manager was awesome. Extremely attentive and helpful. We can't wait to go back!

Stephen R, 01/10/2016

Perfect Family Vacation Home

Our family loved our recent stay at The Captain's Annex in Key West. The home is beautiful, super clean and so well-maintained by the management company -- Shel will make sure that every last detail of your stay is perfect! The house is in a great location that is a quick walk to Duval Street but in a quiet location so that you can enjoy your vacation. We would highly recommend this property to friends and family that are looking for a great place to stay in Key West. Make sure that you stop by My Blue Heaven for breakfast during your is the best. We also loved Louie's Backyard for a special dinner out on Christmas Eve.

Jacqueline T, 12/23/2015

Our entire experience in key west was amazing the house on Eisenhower was beautiful!

This was the perfect family vacation with the perfect accommodations! We look forward to coming back next year!

Kelli J, 12/17/2015

Great property with excellent service

WE had a great stay at the Annex! Property was clean and comfortable. Shel was terrific!! We plan to return to this property in 2016!

Curt R, 12/09/2015

Beautiful & Comfortable

Shel was very accommodating and knowledgable of the area. We visited many of the restaurants he suggested and we were extremely happy with the food and service at these locations. We will definitely be renting this house again in the future!

Vonda & Bill P, 11/20/2015

Perfect location, we loved it!

We stayed here for a week during the Superboat Races. This was much better and more convenient than a hotel (which we normally stay in). Having our own boat dock was perfect! We plan to be back next year! Thanks.

Michael L, 11/09/2015

Exceptional and Perfect

Beautiful, clean home that was in great condition. Check-in was seamless and our agents went above and beyond to make sure that we enjoyed our stay. They were friendly, helpful and even willing to arrange for extra cleaning due to additional people. All in all, very happy with the stay.

Jonathon R, 10/25/2015

Bachelor Party During Fantasy Fest

Great Location, perfect space and even better property manager (Shel, you are the man!!). Walking distance to the nightlife but far enough where you can't hear the noise. Would definitely recommend to family, friends and anyone who wants to rent it.

Christopher M, 10/22/2015

Property was clean, easy access

Amazing! Shel was so considerate and accommodating! I would stay here in the future.


Lori K, 10/07/2015

Terrific Stay

6 of us stayed at the house for 5 nights. It's a great house and we really enjoyed our visit. Shel (who is mentioned in many other reviews) was an absolute pleasure to deal with. He gets 6 stars. Although we had absolutely no issues during our stay, I could tell that if we encountered any, we would have been in great shape with Shel and the management company. We travel often and have rented a lot of vacation properties. We were very satisfied with this one overall.

I gave the property 5 stars (Shel really brought it up to 5 from 4) but there are a few things that could be improved:

(1) very basic spices should be available in pantry such as salt and pepper. In other rentals we've done, there were some dry spices available which renters keep adding to as more people stay there. It's a really nice thing, there's no serious concerns for sanitary issues with dry spices, and should be considered for this property. At one previous rental, there was a message concerning this inviting people to use the spices and encouraging them to add to the collection during the stay.

(2) the kitchen needs a few more pots and pans. Simply buying another set from Costco would be adequate and very inexpensive for the owners.  The kitchen should also have at least two sheet pans. Again, very inexpensive and would probably last for years.

(3) Each unit should have at least one large cooler. Shel picked us up one from another property but this should be standard.

(4) the slider blinds in the second floor bedrooms should be replaced with curtains. There are gaps in the current blinds and they do not provide adequate coverage for the entire span of the sliding glass doors.

Overall, the above issues are quite minor and we would stay again even if nothing changes. Just a few humble suggestions for the property owners and management company. We can't wait to return (and see Shel)!


John S, 10/01/2015

Great Place to Stay

Our group stayed comfortably in this beautiful house. It is only a little over a mile to Duval Street, which we walked back and forth several times to. The house had everything we needed and was very clean. We would definitely come back.

Michelle L, 09/15/2015

The House was Great

The house was spacious and open. Close enough to everywhere you wanted to be on the island. The landlord Shel came around and accommodated our late departure time and gave great suggestions for the beach as well as restaurants and bars. Overall a great comfortable place to stay with plenty of room for everyone.

Seth P, 09/04/2015

Great for family getaway

Really excellent property. Plenty of parking for all four adult couples in our family. Shel was extremely attentive -- immediately got a topper mattress for the third floor bedroom which was a bit hard for one of the couples. The concierge was excellent -- arranging bikes for 8 people. We would definitely consider staying here again.

Thomas L, 08/27/2015

Superb Vacation Getaway

The overall property was just what we were looking for. We had a full house and the accommodations couldn't have been better. Upon arrival we were met at the house by Shel, our property manager and "tour guide"! He went over the in's and out's of the house which was helpful. He also showed us where we were on the local map so we could get our bearings. We told him the type's of restaurants we liked and he recommended many and circled them on the map. The recommendations were spot on! The location was perfect for us, we rented a boat a few days and that was docked 100 yards away! We were within a short walk or a short taxi to many of the restaurants and Duvall St. Shel checked on us during the stay to make sure all was ok and to see if we needed anything. He also made sure we got to the airport ok. I would recommend Last Key Rental to anyone and would use them again, which I am sure I will. The communication before, during and after made things seamless. The only regret I have is having to leave!

Scott f, 08/11/2015

This property was everything that was promised.

The house was beautiful and was everything we had hoped for. However, what would make us come back was Shel Segel (guest service coordinator) who went out of his way to not only make our family experience a special memory, but to provide every kindness and consideration possible. We highly recommend this property and experience due to Mr. Segel's caring and expertise.

Bruce K, 08/01/2015

Great property in key west!

Our extended family of 8 people stayed here for one week. We called Shel when we were just outside of Key West. He was waiting for us when we arrived at the house. He showed us everything we needed to know and also personally met us at check out to obtain any feedback about the property..

The house was three levels. It was very spacious for our group. Very impressed that the air conditioning was just as good on the third floor as it was on the first floor. Bikes are the easiest way to get to town as the ride is flat and short. Only need one car to get groceries to cook in several nights. 

Very impressed with Last Key Realty as Shel and the other members of the team provided excellent communication during the entire rental process. We rented numerous houses in the past and they were the most professional and customer friendly.

Highly recommend this house!


barbara b, 07/18/2015

Everything & More!

This property is everything and more than described. We were looking for a place to accommodate a large group with 3 families and The Captain's Annex was on point. We were kindly met by Shel, the property manager, upon arrival and given a full tour of the home and amenities. The home was spotless and and very well maintained. I have twin 2 year old toddlers and was nervous since they still play a lot on the floor, however, there was instantly no worry once I saw how nice the home was. There are a lot of stairs by the design of the home, so you will get your fitbit flights in here, as well. This did aide in providing the privacy expected for our different families. This comfortably slept 8 adults and 2 toddlers with 2 extra beds leftover. The water pressure for the showers was very good, the fridge and all kitchen appliances were up to date, as well as, a nice assortment of dishware and cookware for the guests was provided. We did cook some at the home, so we were pleasantly surprised about what it came with. The location is off the main hustle of Duval, however, was just a quick ride away on scooters/golfcart. We never had any issues with parking at the home, either, which was an attractive feature with little ones. Also noteworthy, is the private pool on the yard. While not a giant pool, it was perfect for a quick cool off and somewhere for the kids to play with Dad. The back porch and patio area lends itself nicely for cooking out and hanging out with friends after hours. I would also like to praise the concierge service. They were extremely helpful in setting up and coordinating crib rentals, scheduling the scooter pickup for the group and booking fishing charters.  We also liked the local's view and recommendations provided on all of the restaurants. Do yourself a favor and have breakfast at Blue Heaven! Overall, we were extremely pleased and would return again in a heartbeat. It really did provide the vacation experience a busy working family likes with the nice upgrades to make your comfortable. Highly recommend this property.

Mary M, 07/08/2015

Perfect for family and teens

We stayed here with our family and friends in June. The property was very clean and well maintained. Every amenity we needed was available, and if the house didn't have it, our property manager made sure we did. And I am very particular about these things. We brought our boat down from Tampa, FL and we were able to keep it a minute's walk away. It was perfect. 

Our property manager was the best! He met us at the Key West Express upon our arrival, which was so nice. The concierge service was awesome and hooked us up with bike rentals and a golf cart. He got us better deals, too. 

Our teens loved it and we would all definitely stay here again.


Catherine B, 06/20/2015

Great home for a family

This was a perfect home and location for a family vacation. The place was clean, bright and cheerful. The customer service

Elaine H, 06/13/2015

Amazing vacation rental!!!

The Captain's Annex was the perfect vacation home! The 3 bedrooms and loft area was perfect for the 12 people we brought! The house was equipped with most appliances we needed. When asked if there was a crock pot available a new one was purchased and waiting for us when we arrived! :)

The house was very clean and ready for us when we arrived. A few small issues were addressed by the property manager immediately. The pool was the perfect spot to relax in the afternoons.

The property manager was AMAZING. He met us upon arrival and even called and checked on us through the week that we visited.

I would ABSOLUTELY recommend this rental to family and friends. We were very happy and satisfied and will visit again!


Tara K, 06/03/2015

This was a great rental we enjoyed it so much!

Shell was the greatest! We loved him! We really enjoyed our stay there. There was just about every supply you can think of that was there, very thoughtful. We stopped and purchased a lot of stuff since we drove down from Ft. Lauderdale and didn't really need to, I was so surprised! All the information that you could need about the area and restaurants was so neatly laid out in a folder.

The property was clean and well maintained and had the latest appliances even a cake mixer, great location.

Enjoyed the pool also even though it's small.

We went on the 1/2 day snorkeling cruise with Sebago Watersports and had a wonderful time.

We were hesitant at first with all the scamming going on but I can say this is legit. I would recommend the Captain's Annex to all my friends and family.


Julia L, 05/25/2015


We rented the Annex as a second house for our visit. We also had the Commander's Sanctuary but needed additional space to accommodate all our family. This was a great 2nd location, directly across from the Sanctuary. We filled up every bed, but there was plenty of room for everyone throughout the house. The house was clean and updated and had all the amenities we needed. Shel, from the real estate office, was there to greet us and instantly made us feel welcome and comfortable, like friends, not just tenants. We were close enough to town, but far enough away to have a sense of privacy. I highly recommend both Shel and the Captain's Annex if you're looking for a fun, relaxing stay in Key West!


Anne P, 05/12/2015

Great property and great location

We had a large group and varied interests. The location allowed for everyone to engage in their favorite pastimes and come together with plenty of room to spare. Great location and well appointed house.


Anonymous , 05/08/2015

Great Weekend

A group of couples came to Key West to celebrate a wedding and the location and connivence of this house couldn't have been better! The house is located in a cul de sac arrangement with a few other houses which allowed several members of the wedding group to stay in very close proximity!  Shel was very helpful and always accessible. We rented bicycles, which Shel helped set up which made the entire island very accessible. The house was well kept and clean. We especially appreciated the fans, iron, and towel supply! Would highly recommend!

Ben P, 04/16/2015

Dream Week in Key West

Our extended family stayed for 8 days at this property including 6 adults and two - 2 1/2 year olds! They property worked out perfectly for us and the property management staff were extremely helpful. Shel met us upon arrival, walked us through the house and made wonderful recommendations for restaurants - many of which we took him up on! We had thought we could manage by walking to the Duval St area but do yourself a favor and rent bikes. EVERYONE travels on bikes and we used ours multiple times a day (and used the concierge service to rent them). We had a couple flat tires throughout the week and the company was extremely responsive in meeting us to swap out the bikes. Anyone traveling with small children should know that the very large walk-in closet in the master worked perfectly as a small "nursery".  We set up 2 portable cribs there. It was quiet and dark - no windows but it did have an AC vent. 

The pool is small but adequate for cooling off and play with small children. It actually saw more sun than we had originally thought. The only small (very small) annoyance was the noise from the boat yard next door that started fairly early some mornings but it really wasn't a huge problem - especially if you're not around that much during the day time hours. This house is perfect for a large family and/or multiple couples. We would most definitely stay again if we traveled to Key West with a large group.


Sue L, 04/02/2015

Amazing House for Bachelorette

We had a group of 12 women staying at the house for 4 nights for a Bachelorette party. The house itself was beautiful, very spacious and clean when we arrived with lots of linens and towels beyond the bare necessities. Everything was in perfect working order and Last Key Realty was a DREAM to work with. From meeting us at the house when we arrived to taking our late night phone calls asking how to use the oven, no question/want was left unanswered. Shel was extremely professional and helpful, giving us all his restaurant and bar recommendations, as well as checking in regularly to make sure we were okay. I also really appreciated that he emailed us the day before our departure to find out what time he should come to the house to check us out the next morning. It was extremely considerate of him and also allowed the group to fully clean the house and pack up so we were ready when he arrived. All around amazing vacation, we love the Keys, and we loved renting from Last Key Realty even more. I am absolutely certain we will be back in the Keys very soon and renting from this company again.

Emily B, 03/26/2015

Great House, Great Location!

The house was very clean, spacious and extremely comfortable. The location was great! The house is within a mile of Duvall street and most places you would want to go but the best advice we got was to rent bikes to get around. We used them everyday, multiple times a day and it made it super convenient to get around the town and generally just to explore. Highly recommend this house and the service provided by the concierge service. We would definitely stay here again.

Scott S, 03/21/2015

great layout and location

Nice location with plenty of room for the 12 of us in our party. Shel from Last Key Realty did a great job presenting the property and making sure we had everything we needed to make our stay enjoyable. Highly recommend the property, Shel and Last Key Realty.

Chris C, 03/15/2015

Great Weekend

Shel explained everything on arrvial and made us feel right at home. The house was Great House and I would def rent it again

James S, 03/12/2015

Perfect Vacation Home

My girlfriends and I just returned from Key West where we went for my bachelorette party. Captain's Annex was the perfect house for our group of 9 women. It's a gorgeously updated home with a large kitchen, large bedrooms and bathrooms and plenty of room to entertain (and also have your privacy!). One thing to keep in mind -- the home is 3 stories and there are no bedrooms on the main floor, so you may want to consider this if someone in your group is not comfortable walking up and down stairs. Our group didn't mind. While the pool is very small and shaded, the backyard is great for lounging, and the dock/ocean are just steps away and perfect for sunbathing. Our house coordinator, Shel, was also incredible. So kind, welcoming and helpful. Last Key Realty really runs an amazing, professional business. I HIGHLY recommend this home for your future vacation!

Sheena M, 03/05/2015

Great spot

Very nice house. Very clean. Fit our group of 11 perfectly.


david f, 02/12/2015

Wonderful Place

This was my 2nd time staying at this property and I definitely hope to stay here on my next visit to Key West. I'm trying to think of any complaints I might have to warn others, but I honestly can't think of any. The place is great, and the property manager, Shel, makes the check-in/check-out process painless. I only had to call him for check-in/out, but he always answered my calls promptly and all I had to do was call him when we were 10 minutes from the property (we drove in) and he was there waiting for us and gave the tour/walk-thru, answered any questions, and was very polite and professional.

Whenever I tell stories of my Key West vacations, I never fail to mention how much we all loved the place we stayed.


Chad C, 02/07/2015

Very clean, comfortable and luxurious.

Our visit was the entire month of Feb 2015. The property is very well maintained and management is eager to correct any imperfections (if you can find any).  We were very comfortable, the house was incredibly clean and all appliances worked. Decor is very tastefully done. Property management (Shel) is very helpful and prompt. If I had to list a downfall... Maybe a bamboo shade for privacy on back porch. Well worth the money, would definitely stay again and recommend to others. It's easy to see the owners spared no expense to make their guests comfortable and have a vacation they will have no regrets with. In a word, perfect!!!!

yvonne l, 02/01/2015

Would love to go back again..and again..and AGAIN!

We were 8 women celebrating a 10 year Reunion Vacation and we NEVER expected the rental house to look exactly like the online pictures--but it did! The house and furnishings looked brand new.

Our manager, Shel, was wonderful to work with--always available to lend a hand, provide detailed information, and he went above and beyond to ensure our reunion vacation was one we would always remember. The concierge services were easy to work with both before our arrival and while we were there. Their recommendations for restaurants and rentals were "right on." 

Would we use Last Key Realty again? You betcha --in a heartbeat! Can't thank Shel and Last Key enough!


Barb A, 01/29/2015

Wonderful Place to Stay

We loved this place and the Last Key did a wonderful job of accommodating our last minute need for a rental. We had 6 adults and 3 small children in this place and it worked out very well. It is beautiful inside and out, the neighborhood was really nice and clean. The pool is a perfect size and was were we spent a lot of time! You are close to downtown but far enough that it is quite. I highly recommend this place as well as the rental company and its staff. Everyone was friendly, informative and went above and beyond to get us a place for the week. If you need a place to stay I recommend calling them!

Kim S, 01/17/2015

Great Crew home for KWRW

We usually try renting a home that can accommodate our sailboat racing team and this house was one of the better experiences we have had to date. The house was big to fit the majority of the guys and had a nice common area. The location was a short 5 min bike ride to the marina or a 15 minute walk. Be aware that if there is alot of people staying in this house that the main level is open all the way up to the 2nd and 3rd floors so noise carries.

We did have a cook with us that thought the kitchen utilities were lacking in regards to cooking for 12 people. We resolved this by purchasing our own required items, we had hoped to be reimbursed for the full amount of the items but only received half of the value.

All and all a great home and if we come back to KW we will be looking to grab this home again.


Matthew G, 01/15/2015

Enjoyed house for our family Christmas vacation

Overall, a great house for our Christmas vacation. The house was nicely appointed. 

It is within walking distance to Duval St, but just barely. Consider this if you have older or very young people in your party. The layout is such that 6 people share one bathroom on the top floor, while the other two bedrooms have in suite bathrooms, and there is a powder room on the first floor. We had 12 people in the house, and ate in for breakfast and lunch, and had to run the dishwasher quite frequently to keep dishes and flatware available. This house definitely needs more. 

We were there during the week, and the noise from the boat storage lot next door started early and was very loud.

Shel is very friendly and gave us some great suggestions for dining out.  We also rented bikes, they were delivered, which was very convenient.

Loved the fact that garbage recycling was available.


Pam W, 12/20/2014

Family Getaway!

Absolutely loved the property and Shel! We were a little concerned having never rented a house in Key West before and wasn't sure if it was going to be what it looked like. But everything was just as pictured and Shel was beyond accomidating to us. We were an odd mix of a group and the beds and bedrooms worked out perfectly! Everything was clean and practically brand new. I would definitely recommend this property to friends and strangers and plan to stay again! The location was great as well just a short traveling distance from Duval and all the attractions! Thanks for everything! LOVED IT


Alissa F, 11/06/2014

Great Stay!

Great property and great location...The house was perfectly clean and well decorated. We had 1 small issue with a bathroom and not only was it taken care of IMMEDIATELY, we were issued a partial refund as well. This was above and beyond. Would definitely stay here again!

Dave , 09/25/2014

40th Birthday Party

The house was great. Pool was a bit small but it turned out to be perfect. Of course you can't do laps but for the purpose we needed it for(relaxing with a beverage) it was just fine. Good location, short bike ride (renting bikes is highly advised) to Duval and basically everywhere else you need. We parked the cars and never needed them. The private dock slip was great for our jet ski's also.  Shel our host was great. Was there to greet us and there to see us off. Will definitely stay here again when we make it back down.

GEORGE V, 09/18/2014

40th Birthday Celebration

Property was as described. House was very clean and well maintained. Shel was great. The day after our arrival the road was being re-paved. It was a nuisance for a few days and very loud. I will not fault Shel for that since he was not aware and was apologetic.  We had 9 adults in our group and made the best of situation. Would definitely stay here again (barring any construction).

We made it to Duval Street and Mallory Square several times. Lots of fun! Breakfast is the meal to eat in Key West. Fort Zachary Taylor beach was nice. Wear swim shoes, the rocks are sharp!


Adrianne M, 09/07/2014

The house was great! Shel was great!

The house was exactly as shown on the website. Everything was clean and the house was in great condition! The house had everything we needed for the week. Kitchen was fully equipped! The concierge service was very helpful in finding restaurants and things to do. Our experience was enhanced with the great service from Shel. He welcomed us, and made us feel right at home. He checked in to make sure we had everything we needed throughout the week and his recommendations were spot on. Thanks for a great week!

Jessica H, 08/30/2014

Great location, lovely home

Great home and very convenient boat slip if you are bringing a boat. Duval st is a 20 minute walk or 5 minute cab ride. Home is beautiful and very clean,

Viti C, 08/09/2014

Fabulous vacation home!

We had a group of 13 including myself and the house met all of our space needs. The home was clean, beautifully furnished, set-up well for cooking etc... We couldn't have asked for more-it was definitely worth the price!


Cheri H, 07/28/2014

Beautiful home for a much needed vacation!

Very beautiful well maintained rental with all the amenities. Great location. Our family loved renting bicycles to explore Key West. Shel the property manager was always available to help us with great recommendations from Beaches, great coffee and restaurants. We loved the Hogfish Bar & Grill. Thanks for a great vacation!

Neisa M, 07/14/2014


We rented the house for a week and it could not have been any better. First off, Shel was excellent. He was very friendly and made sure our stay was the best it could be. They offer a concierge service that delivered bikes to the home and also picked them up upon our departure. They also booked a jet ski tour. We were regulars at Dante's because the pool was a bit small for our large group but the pictures clearly showed the property so we knew in advance the pool wouldn't be large enough. We would DEFINITELY recommend this place to any group looking for a spacious home and friendly and accommodating staff.

Karen S, 07/14/2014

Nearly Perfect!

Upon arrival, my first thought arriving with a group of about 10 guys for a bachelor party was this is far too nice for us!  Luckily the whole group was well behaved and, luckily, treated the place (on my credit card) respectfully.  Everything was immaculate upon arrival and was one of the major highlights of our trip. I would definitely come back.

We were able to grill a few nights to keep our costs lower and had an all around wonderful time. I forwarded a member of our group the details of this place so they could book a family getaway in December so it attests to how great it is for all types of groups.

Shel, the property manager, provided us with enough information to order food (Caroline's!), bikes and cabs to let everybody enjoy their days and get home safely at night. He provided no hassles whatsoever, laid back and very straightforward.

Cons: The pool is kind of small and it is about a 15 to 20 minute walk from Duval. I happened to like the distance since it was away from the hustle and bustle but others in the group complained. I highly suggest renting bikes, they deliver and pick up!


Andrew W, 07/10/2014

Great House!

House was beautiful and larger than we expected. More than enough room for our 3 families - 11 people total. Shel was wonderful and always available to answer any questions we had. We had a wonderful week in the Captains Annex!

Kristin N, 06/29/2014

A Bachelorette Party to Remember!

Myself and 12 other women stayed at the Captain's Annex this June 2014 for a bachelorette party. Most of us were in our late 20s with a few in their mid 50s and we all had an amazing time! The house is absolutely breath taking and HUGE! We loved the privacy of not being directly on Duval but also loved that it was a short bike ride away (I definitely recommend renting bikes -which you can do through their free concierge service- it was an adventure in itself). The house was immaculate and the pool area was a great hang out spot! I can't speak more positively about the house or our time there! Thank you Shel for being more than accomodating and making our stay absolutely magical!! <3

Shannon F, 06/19/2014

A great place to stay

The house was immaculate - everything we had hoped. There were 9 of us and we had room to spare. Of course, the top floor of 3 was where 6 of the beds were located so some of us had a chance to work off a bit of the fine Key West food. The staff who handled the rental was great and we got checked in and out with maximum efficiency. Shel, the agent with whom we had the most contact, stopped by three times to make sure we were happy. He provided a great deal of information that we used on several occasions, like how to make reservations for both the restaurants and various attractions and which of each might be best for our group which included 3 children. We had a great time.

Richard W, 06/12/2014


This home provided so many amenities and the guest service coordinator, Shel, was extremely helpful. In fact, we had some pressing business and the management company staff assisted with our request to scan documents and print material. I would highly recommend this rental based on our week-long vacation experience.

mary s, 06/02/2014

Great vacation at The Captain's Annex @ Paradise

The house was great. It was clean and had everything we needed. It was a great location. Close to the fishing dock that we used for our fishing trips. We rented bikes which was great. Only a 10-15 minute bike ride to wherever we went. Shel & the staff were very helpful in helping us book our activities(fishing, jet skiing, parasailing). Had a great time. Can't wait to go back.

Anonymous , 05/24/2014

Awesome Place

House was everything it was supposed to be.

Great location, over the top amenities and awesome management that made sure everything was perfect.

Will defiantly be staying again.


B M, 05/14/2014

Beautiful and comfortable

Rented this house for 8 girlfriends to celebrate 50th birthdays. The property is beautiful and very comfortable for all of us. The property manager, Shel, was very attentive and responsive to anything that came up. We had a wonderful time. Give this 4 stars, we would have enjoyed being a little closer to town and a larger pool since there were 8 of us. It would be perfect size for a little smaller group.

Gayle H, 05/08/2014

Beautiful Home!

We had a wonderful stay at The Captain's Annex. Plenty of room for our large family. I would definitely recommend this property to a friend! Very well maintained and Shel was an excellent host!


Carla F, 04/30/2014

Outstanding Property!!

This is a wonderful property - very clean / perfect for a big family or a reunion of college friends. The furnishings are high quality and comfortable. reasonable walk to all the action. We loved the cuban restaurant nearby.

Shel was very professional and eager to please. I would absolutely recommend this property to a friend or relative.


Greg K, 04/04/2014

The property was clean and beautifully furnished

The property was very clean and beautifully furnished. Our manager (Shel) was always there for us whenever we needed anything. He was unbelievable! The location of the property was perfect for close to the water, convenient parking, and away from the downtown bustle. It was a great week that we will never forget.

Kathy P, 03/31/2014

Perfect place to stay in Key West

So glad we found this house to stay at during our week in Key West. The house was clean and beautiful. The property manager was very kind and informative on what to do during our stay and what to eat. He checked up on us during the stay to make sure everything was going well. He accommodated our early arrival and late departure. The house really is the perfect place to stay in Key West. We rode our bikes to Duval Street every night, which was so much fun. We had a rental car, but didn't even use it. Will definitely stay at this house next time we make it to Key West, which will hopefully be soon. The house contributed to our amazing week in Key West.

Julie R, 03/09/2014

Terrific Property

This was a lovely, well-maintained home with plenty of amenities. It had more than enough room for our family and guests, was nicely decorated and really quite pristine for a rental. The downstairs living area/kitchen was very well laid out and decorated, as were the bedrooms. The residential area was quiet and you couldn't really hear the neighbors. What made this residence awesome was the helpful folks at Last Key Realty, from the rental agents and receptionist to the Concierge Service people and, above all, Guest Services Manager Shel Segel. We had an easy check-in with lots of important information provided regarding the property, restaurants, things to do, vehicle rentals, etc. The property is quite a hike from downtown (Duval St.) so we opted for scooters and bike rentals. Bikes were promptly delivered to the home. Any issues we had were attended to promptly by Shel and Last Key. My son lost his wallet and had to have a passport express mailed, and they kept and eye out for it and Shel immediately delivered it to us! The pool area is small, and quite shaded, but we were able to enjoy it. It was much more fun to take the bikes to the beach (Higgs, Smathers), which only took about 10 minutes or so to get there. Shel's dining recommendations were perfect and we just really had a great trip. If you need a large property, and don't mind being a bit of a walk from Duval, this is the perfect property.

Mary V, 03/01/2014

Beautiful home

We truly enjoyed our stay. The property was very clean and had everything we needed. Shel was a wonderful host and made us feel very welcome. If we called...he answered. We will definitely use Last Key Reality again.

SHERYL W, 02/20/2014

Awesome setting and rental!

We rented this house for a group (12 people) arriving in Key West for the Ragnar Relay. We had a wonderful time and the property was excellent. Shel, the Guest Services Coordinator kindly met us upon arrival and made sure we had everything we needed. We had arranged for bikes to be delivered upon our arrival and they arrived shortly after we did. Everything was wonderful and we would recommend renting this property.

Thank you!


A guest from l, 02/08/2014

Lovely home in Key West

We stayed at The Captains Annex for one week. We were three families with 5 children. The house was great and had everything we needed and more. Shel, the guy who was our contact person, did a fantastic job and helped us with everything. He also organized that we could rent highchairs and strollers for the kids.

The Captains Annex served as a perfect home base during a fantastic week when we could explore Key West and the surroundings, including beaches, restaurants, shopping and museums.

Built only a couple years ago, the house contains all modern functionality you could ask for and has a clean, upscale interior with a nice touch of traditional Key West architecture.


Frida F, 01/10/2014

Great house, amenities, and service

We were greeted upon arrival by our very friendly and helpful guest services coordinator, Shel. He showed us around the property and gave us a preview of restaurant recommendations and potential activities for our vacation.

The house was exactly as described in the listing, and perfectly clean when we got there. The property has plenty of room for a large family or group. We particularly enjoyed the open floor plan on the ground floor that allowed our whole party spend a lot of time together.

The only problem we had our whole trip was that the central AC stopped working during one of our first nights. The next morning we called Shel and he had a technician come fix the issue before noon. Very good service, all things considered!

While the property isn't that close to Duval Street, it is only a 10-20 min walk to get to the action. You could also drive into town since the property has 2 convenient parking spots. However finding parking in town was a bit difficult during the evening.

All in all a very nice place to spend a few days or a week + very good service from the realtor, Last Key Realty.


Ben S, 12/27/2013

Great property

This was a very nice home that worked perfectly for our trip. We were attending a family wedding and the house worked as a great base for our Key West exploration. The house had everything we needed and Shel, our property manager, was terrific. He was very responsive and helpful with suggestions.

Marian D, 11/12/2013

We couldn't have wanted for anything more!

VERY clean and well kept with accurate online pictures/descriptions.  Thoroughly stocked and met all our needs...right down to nice sized pool towels.

After experiencing the (not even peak-season) hustle and bustle, this home was pleasantly peaceful and well located for our stay - we were only 2 minutes from Conch Harbor Marina where our sailboat was docked.

Shel's support really made us feel like we had been there a million times.  He was like an old friend glad to see us finally arrive and was he going to be sure we were well cared for. 

Thanks also for being flexible in accommodating our ever changing sailing schedule and we will recommend you and your properties in the future.

Amy & Dan, Gerry & Sara, Ken & Jane, Larry, Rick


A R, 11/12/2013

Bachelor Party in Key West

Gorgeous house, complemented by a friendly, informative, and honest agent, Shel. It was an absolute pleasure dealing with Shel, as I've had bad experiences booking houses in Key West. When I come back, I will make sure to have Shel as my main point of contact. 

The house was spacious, clean, and very accomodating for our party of 12.  Everything you want out of Key West is a 3 minute cab ride away. I highly recommend both this house and especially Shel for any booking needs. I truly felt taken care of, which is not a point I am able to often make when renting houses for various trips around the country.

Thanks again for everything! I look forward to our next meeting!


George M, 10/18/2013


No questions found, click the button below to ask the first one!

Ask A Question

Travel Dates

Minimum night stay:
From 3 nights

Want To Know More About This Listing?

Leave this field empty

Fill out the form below to get more information.