Cool Breeze

$0.00 Weekly
Unit Type: Townhouse
Pets Allowed: No Pets
Address: 231 Southard Street Key West, FL 33040
Neighborhood: Truman Annex
Stay Type: Weekly, Monthly

Overview Read Reviews

Cool Breeze has been thoughtfully furnished & decorated in tropical style…
Living room has a home office and a TV. So it is your choice: work or leisure...
French Doors open up to the spacious back porch...
The private back porch is shaded and has an outdoor fan...
The back porch has an outdoor dining set, perfect for dining for four al fresco style...
The sofa will convert to a queen sized bed for the convenience of your guests...
There's also an indoor dining set for four next to the kitchen...
The efficient kitchen is fully equipped to prepare any meal you might want…
The kitchen reflects the same sense of tropical design as the rest of the house…
There is a powder room near the living room...
Cool Breeze also has a front porch, the perfect place to relax with a good book...
You can also sit our here and people watch all afternoon...
Both of the bedrooms are located upstairs...
Each bedroom is located at an opposite end of the hallway...
The master bedroom has a King bed and flat screen TV...
You'll have plenty of closet space...
The master bedroom also has a private balcony...
Large French doors open to the private master balcony...
The master balcony has comfortable seating...
You'll be able to enjoy the island breezes while still being in the shade...
The master balcony is an ideal spot to sip your morning coffee...
The master balcony has a view of the pool...
The master bathroom is en suite, with a walk-in shower...
The master bathroom has a large vanity and mirror...
The second bedroom is at the other end of the hall...
The second bedroom has a Queen bed and overhead fan...
The second bedroom gets plenty of natural sunlight throughout the day thanks to the wall of windows...
The second bedroom also has great closet space...
The second bedroom has a mounted flat screen TV...
The second bedroom also has an en suite bathroom...
The second bathroom has a shower and tub combo...
The washer and dryer are located in the upstairs hallway...
The backyard has a private entrance/exit through the gate...
Take the path through the back gate to the community pool...
The community pool is just steps away...
The community pool has restrooms for your convenience...
The community pool is large enough to swim laps...
The community pool has plenty of chaises for everyone...
Spend the warm South Florida days cooling off in the pool...
Cool Breeze is nestled in the quiet gated community of Truman Annex...
Truman Annex is Key West's most exclusive gated community in the heart of Old Town...
The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night...
Your rental includes a covered off-street parking spot...
Fort Zachary Taylor State Park Beach is located is located a couple blocks away...
There are beach chair and umbrella rentals at Fort Zach...
Get out on the water and enjoy the beautiful Key West waters during your stay...
Fort Zach offers both sun and shade, as well as picnic benches and grills...
Grab a snack or drink at the Fort Zach Cayo Hueso cafe...
Take a tour of the actual Fort on your way to the beach at Fort Zach...


"Feels like home! I stayed at this property with 5 other family members and we had a wonderful experience. The home is well maintained and is very spacious even with a large family. The staff at Last Key went out of their way to assist us with our vacation. By the end of our stay we felt like we were right at home. Highlights: -The pool is private and secluded -The property is very close to Key West attractions I would recommend this property to anyone who plans a visit to Key West." -Lindsay H. 08/13


"Cool Breeze" is a charming villa that is located on the President's Walk in the Truman Annex, Key West's most exclusive gated community in the heart of Old Town. You'll be a short walk from the best restaurants and attractions; including Sunset Pier, Duval Street and the sunny, sandy beach at Fort Zachary Taylor State Park. You won't need a car because it's all right outside your door. Just for fun you can rent a bike or scooter from the shop just one block away, right next to a deli/convenience store.


As you enter, you'll be struck by the distinctive Spanish tile floors and tropical colors. At "Cool Breeze" enjoy seamless indoor to outdoor living via the French doors to your own covered patio. The living area also offers a comfortable sofa bed for extra guests. The large flat screen TV is great for those times you need a break from Key West's night life. You can also stretch out under the shade of the manicured vegetation and palm trees on one of your three covered porches. Great people watching can be had on the covered front porch overlooking Southard Street. The kitchen is fully equipped to prepare any meal and you can dine either indoors or outdoors. A powder room is just off the living area.


Just outside your back door is the community pool with ample chaises, tables and chairs and umbrellas. Key West's famed Fort Zachary Taylor State Park, with the prettiest beach in Key West is down the block. "Cool Breeze" has provided all of the necessary beach gear for you including towels, beach mats and a cooler.


Both bedrooms are on the second level of this two-story villa. The master bedroom with its en-suite bathroom has a king bed, flat screen TV, large closet and double French doors to the covered balcony. The second bedroom has a queen bed, flat screen TV and also has an en-suite bathroom.


Central Heat and A/C, Ceiling Fans in All Rooms, Cable TV in Living Room and Both Bedrooms, DVD Players, Wireless high-speed Internet Access, Free US/Canadian Long Distance Phone Service, Fully equipped kitchen with Microwave, Blender, Toaster, Ice Maker and Electric BBQ, Linens, Towels, Hairdryers, Assigned Carport Parking, Daily or weekly housekeeping provided upon request. This property will accommodate 4 to 6 adults.


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Map may not be 100% accurate.


  • Area - Truman Annex
  • Property Type - Townhouse
  • Floors - Two Story Home
  • Bedrooms - 2.00
  • Sleep Cap - 6
  • Rental License Period - Weekly, Monthly
  • Approx Sq. Ft. - 900
  • Pets - No Pets
  • Parking - On-Street


  • Number of Seperate Beds - 3
  • Bedding Bed 1 - King
  • Balcony Bed 1
  • En Suite Bathroom Bed 1
  • Floor Bed 1 - Second
  • Bedding Bed 2 - Queen
  • En Suite Bathroom Bed 2
  • Floor Bed 2 - Second


  • Number of Bathrooms - 2.5
  • Bathroom 1 Size - Full
  • Bathroom 1 Type - Shower Only
  • 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 - Half
  • Bathroom 3 Floor - First

Indoor Amenities

  • Sleeper Sofa - Queen
  • Sleeper Sofa Mattress - Standard
  • Dining Room Seats - 4

Outdoor Amenities

  • Pool - Community
  • Grill - Prohibited by Fire Code


  • Living Room TV - Standard

Recent Reviews About This Property

Great location

The condo was perfect for us and had everything we needed for a week long stay. It looked just like pictures advertised. The king bed was very comfortable (my husband and I both have back problems). If I could change anything it would be to add drawer pulls on both bathroom vanities. Loved the location to everything, no car is needed. We enjoyed the pool which was right behind condo. The outlets in bedroom are behind the bed so some type of power strip or extension cord would be helpful. There were plenty of bath and beach towels. The kitchen was stocked with everything we needed. We will definitely will stay here again.

Julie S, 08/03/2018

Response from Last Key Realty:

Thank you for reviewing your stay and for the thoughtful suggestions. We're continuously looking for ways to improve our homes and enhance the overall guest experience. With that, we do agree your suggestions would be very helpful to future guests staying in this home and have arranged for these items to be installed. Hope to have the pleasure of hosting you at Cool Breeze again!

Perfect Location to everything!

We loved staying in Truman Annex, the absolute most perfect location (in my opinion). We were close to Duval, Ft. Zachary, Southern Most Point, Bahamas Village and the marina. Yet it was so quiet and peaceful once we arrived "home". The house was a great size for 4 adults and 1 pre-teen. The house had everything we needed (kitchen, bathrooms, rooms, linens, etc.). The bathrooms were smaller than I expected and a bit tight (just FYI) but that didnt cause us much issues. The AC was great, kept the house nice and cool, so when we returned home from August KW heat, we were able to cool off instantly.

The concierge service provided during our stay here was fantastic. We had our bikes delivered to our front door (and picked up at the end of our stay), our exursions booked and our jeep rental booked lightning fast with no issues. Our main contact Keith was also wonderful to work with and super accomodating for us and ensured we were taken care of with flights in and out.

The house is definately a classic Florida feel, tile floors throughout, fun colors, and great local artwork everywhere! if the artwork were for sale in the house, I would have bought a couple pieces! I liked that we didnt feel like we were going to ruin anything (not fancy and easy to clean/sweep if you need) - in and out from the beach, ocean, kayaking, fishing, etc. Nice outside seating both front and back porches.

Parking was tight in the designated space. There was a monster truck parked in the space behind us and it would take a 20 point turn to get out of our space (no joke). The space is covered and has posts on either side which didnt help with getting in and out. The bright side - we had a parking space so we didnt have to pay for parking. We also parked our bikes there until security told us we couldnt. So we started parking in the back yard... with 5 bikes (one being an adult trike) that was not the greatest set up, but didnt know where else to park them.

All and all, we will stay here again anytime we visit Key West.

Angie , 08/03/2017

Better than advertised

We loved this charming place! Convenient walking and biking to restaurants and attractions with everything we needed. The parking space was a little challenging to get into, but we were glad to have parking included. A great stay with great service.

Beth G, 07/22/2017

Great holiday vacation spot

Very nice stay during the holiday at this home. Convenient location for walking all around the downtown and the Duval Street area. Morning coffee on the front porch, watching the famous Key West chickens was fun! We took home some great video of their shenanigans! Blue Heaven became out favorite hangout spot for breakfast and dinner. The house was extremely comfortable for the 3 of us and we would stay here again. We had a little problem with the internet, but our manager, Lori came by right away and took care of it.

Gabby Z, 12/19/2015

Great place and location!

My husband and I stayed at Cool Breeze with another couple and we all really loved our stay! The location is so convenient to all of the action yet the community is tucked away a little so the area felt safe and was quiet late night. We found the property to be very clean and comfortable and would absolutely recommend it to anyone! Since our group was made up of two couples it was nice that each of the bedrooms upstairs had an attached bathroom and having the third bathroom on the first floor was super convenient. Five well-deserved stars!!!

Lisa , 12/08/2015

Pretty townhouse in old town

We wanted a romantic getaway and this was it! Very cheerful colors inside the house and it was so clean and very comfortable!  We did enjoy some paddle boarding, Ft Zachary Taylor Beach and many sunsets (and margaritas too!) Best dinner we had was at Michael's. The scallop appetizer there is so amazing! I would certainly recommend this house and Last Key Realty. A big thank you to Lori, for her amazing service during our visit.

A T, 11/16/2015

Our 2nd year at Cool Breeze

This home is exceptional! My wife loves this house and we all enjoy the back patio for our morning coffee. The location for race week is perfect! This is our second year staying at this home. We are already signing up for Nov 2016. Lori is fantastic and we can't imagine staying anywhere else!!! See you next November!

L M, 11/07/2015

Wonderful home with great location and service

This was such a perfect home! We all fell in love with this colorful place! We walked to all of the festival celebrations and events downtown. Even our grocery shopping was taken care of for us by Lori, who was also the manager. Lori did a wonderful job seeing to all of our requests. It was a real pleasure dealing with such a professional company and staff. This home had everything we could possibly need or want. We are already looking forward to fantasy fest next year and certainly will use Last Key again.

D B, 10/26/2015

Cool Breeze

Great place, nicely decorated, clean and perfect location!! Can walk everywhere.

Kay K, 07/22/2015

Our Cool Breeze stay was perfect!

It felt like a tropical dream when we walked in the door. Everything was pure bliss! The air was cool and the home was wonderful! Bright, fun colors surrounded us in every room. You can't help but to feel happy when you are in this house! Perfect location for walking to all the delicious restaurants nearby and for sightseeing. Loved Cafe Sole and Michael's for dinner and Mallory Square for sunset. Our reservations person and house manager, Lori was so helpful. From planning to our reservation to staying in the house, Lori was on top of everything for us. She immediately made us feel welcome and her attention to every detail of our stay was so pleasant and very professional. I feel that Last Key should be the first choice, for any vacation you plan in Key West.

L H, 06/11/2015

Best location and wonderful hospitality.

Could not have asked for a better vacation in Key West. Everything in this home was pure perfection! We could enjoy a home cooked breakfast on the patio and then drinks in the afternoon. Just a very short stroll to our favorite watering hole, the Green Parrot. Lori provided all of the down home hospitality we could have wanted! This stay was such a fantastic experience for us, that we are already checking our calendars to plan our next trip to Key West. We will definitely use Last Key again. See ya'll again soon!

R H, 05/02/2015

Spring Break Success

Our family stayed in this condo for Spring Break and it was absolutely perfect! Great location for accessibility to Key West and the community pool! Nicely Furnished and loved the outdoor patio table for relaxing after a fun day around town.

Darla H, 03/22/2015

Had a perfect stay again this year!

Loved the blooming orchids and new blinds! We continue to enjoy the restaurants and easy access to everything Key West offers. Thank you Lori and our handyman who changed our light bulbs and adjusted the fan within the half-day! We will be back!

Linda K, 02/01/2015

What a truly wonderful place we have found

We have vacationed in Key West many, many years. We were so very lucky to have found Lori and this incredible home. It must have been fate when we ran into Lori last year. We were so anxious to find a beautiful spot for 2015. She found us this town home, that we plan to stay at again next year and hopefully for many years to come. Thank you again Lori and see you in 2016!

R S, 01/03/2015

Ringing in 2015 Key West style

What a wonderful home! The best location for walking to all of downtown. This cute townhome was immaculate and beautifully furnished. Impeccable service from Lori made our trip spectacular! We highly recommend this home and this company. 5+ stars for this fantastic house and for Last Key Realty that helped us rent it.

M S, 12/27/2014

Enjoyed every minute here

We loved this home. The perfect location and best of all, the great service we received. It was the perfect surprise for my wife and her friends.

e b, 09/13/2014

Tres Bien!

We liked Key West and this villa very much. We travel quite a bit, as a family and Key West Florida is a new favourite. The villa was very well located for walking and bicycle riding. Happy, bright colours inside with comfortable beds. We enjoyed our vacation here tremendously.

S L, 08/01/2014

Wonderful Key West trip

We had a very good time in Key West. The house was so nice and very clean. The swimming pool was just outside our back gate. We were glad to be able to walk to restaurants and to see the famous sunsets. So many wonderful things to do and see. Thank you.

P R, 07/20/2014


Lori made sure our KW vacation was perfect and it was! As in any vaca, there was a tiny bump (no fault of Lori's at all) yet SHE handled superbly and enhanced our vacation even more! The house was immaculate and everything you could imagine that would be in your own home was in this house, but nicer! lol We thank you so much for a wonderful time and kudos to Lori!

anne w, 07/07/2014

Great place and a great time!

We loved the location and this home. Everything went smoothly and I highly recommend this property. Thanks again for a great trip.

Jeff F, 06/28/2014

A Wonderful Stay

Lori was a joy to work with from the moment I booked Cool Breeze till she met us at the condo after hours to let us in. Condo is just steps inside the gate of Truman Annex and is as cute and clean as the pictures show! We are KW regulars (4 times this year alone) and have used several rental companies...Last Key will be the ONLY company we use from now on! Super clean house, great location, fantastic staff!!!

stephanie j, 05/28/2014

Beautiful sunny stay in Key West

Key West was our choice for this year and what an excellent destination. This home was so clean and well cared for. We were very impressed with the attention to the smallest details. Lori was our service manager and she was prompt, professional and so helpful. The concierge assisted us with some water activities and we had a wonderful stay. We have recommended this home and Lori to our friends, who are planning to come to Key West this summer.

r j, 05/15/2014

Cute as a button!

I have so many nice things to say about this home. It was close walking distance to everything, especially Mallory Square for sunset. Fun to "people watch" having morning coffee on the front porch. This cute home was so clean that we felt like the first people to ever stay here. Lori was very helpful and provided us with so much information on places to eat and things to do in Key West. The concierge was also very helpful. We all had a wonderful island vacation!

C A, 05/07/2014

PERFECT place to stay.

It was great place so cheerful and nicely updated. The front porch was a great place to sit at night and watch the town go by. The pool was perfect we enjoyed sitting by the pool daily. The townhouse was in walking distance to everything you could want a few blocks off of Duval and about a 20 minute walk to the marina. this was the perfect place to stay. We would definitely stay here in the future.

Heather P, 03/29/2014

Perfect location

This charming town house is so perfectly situated that you never need a car. We strolled Key West so easily from here. The house is lovely and we immediately felt like we were in the tropics when we came through the front door. Sunset at Mallory Square was a favorite in the evenings and Lori made some excellent dining suggestions. The free roaming chickens and roosters only added to our Key West experience here. We even saw some baby chicks in our yard. We highly recommend this home!

d p, 03/08/2014

A good time for uas all

Key West is one of our favorite vacation spots. This home was the best by far of all we have rented. Location was perfect, home was spotless and our service manager Lori was helpful and sweet! This home was an excellent choice for our group vacation.

L S, 02/23/2014

Perfect for our month in Key West

Cool Breeze was just what we needed to enjoy all Key West offers. It was perfect for us when we had visitors and when we were on our own. Short walks to great food and music. Busy front porch for viewing, quiet back porch for dining. Lori was very responsive to our requests and the few suggestions we made were honored quickly by the owners. Peter helped with our maintenance request with humor and excellent service. The staff at the office kindly and pleasantly helped me get some downloads printed and mailed. We felt like it was our home in Paradise.

Linda K, 01/26/2014

Convenient to everything

This property was within walking distance to everything yet it was in a safe and quiet area. We only used our rental car once to go to the grocery. It was clean and well maintained. Lori Bailey was available to help up with anything. I would recommend this property if you want a cute and relaxing place to stay in Key West.

Susan , 12/21/2013

Fun place to stay in Key West

We were so pleased with our stay at this townhouse. We could walk everywhere and enjoyed watching the people pass by while having coffee on the front porch in the mornings. Lori was very helpful and the activities were well orchestrated for us. I highly recommend this home to everyone that wants to experience a lovely stay in Key West without needing a car to get around.

k b, 11/23/2013

Perfect location for family vacation

We stayed at Cool Breeze for our family vacation. We found the home to be even better than we anticipated. No need for a car here. Everything is within walking distance. Lori was very helpful to us during our stay and we give her and this wonderful town house 5 stars and more!

k m, 09/17/2013

Feels like home!

I stayed at this property with 5 other family members and we had a wonderful experience. The home is well maintained and is very spacious even with a large family. The staff at Last Key went out of their way to assist us with our vacation. By the end of our stay we felt like we were right at home.


-The pool is private and secluded

-The property is very close to Key West attractions

I would recommend this property to anyone who plans a visit to Key West.

Lindsay H, 08/21/2013


This is a great place to stay. It is so "Key West" decor, comfortable and homey. It is in walking distance of everything and very quiet and relaxing in the evening. Lori Bailey was so nice and helpful. I would recommend this to anyone wanting to stay in Key West. Thanks for helping make our vacation Fantastic!!!!

Jerry & Carol S, 08/10/2013

Response from Last Key Realty:

It is our primary goal to always "help make your vacation Fantastic" so it is truly a delight to hear that we achieved that. Staying at "Cool Breeze" is really the total package in terms of a convenient location, Key West design, and a helpful Guest Services Coordinator who is dedicated to making sure you enjoy yourself while on the island. We hope you were able to take advantage of a bit of the island's best "people watching" from the front porch!

Beautiful Home

This place is fantastic. It is everything they say and more. Lori is great. She was VERY helpful and a great asset. She made us feel very welcome and right at home. I would recommend this place very highly. Can't wait to go back.

Jerry & Carol S, 08/10/2013

Cool Breeze

as soon as we walked in we loved Cool Breeze - Red Tile floor first floor and all wood floors elsewhere it was everything we wanted. There were four of us: two who drank decaf and two who drink regular coffee so we asked Lori to bring us a second pot and she did so the very next morning. Everything occurred just as Lori said it would and she gave us some personal favorite restaurants to choose from. The property is just 2 blocks from Duval and the island has the flavor of Cuba or some other Caribbean island - narrow streets, not alot of cars, bars, restaurants, clothing stores, souvenirs and all were great but what really pleased us were the roosters, hens, chicks and kitties loose throughout the tourist area whom we shared the streets with and it was our pleasure to do so.


Cool Breeze has a shady front porch as well as back porch and it was about thirty steps from a refreshing pool.  Personally, I would not wish to vacation elsewhere - the walks helped me lose a pound or two of winter weight.  And the shocker of the whole trip, unbeknownst to me, was the fact that Ernest Hemingway was awarded the most prestigious of war medals... the "Medal of Honor".  Visit his home to find out which country gave him that award!!!


Phil Micciche


North Canton, OH  44720


Phil M, 05/08/2013

Cool Times at Cool Breeze

Loved it! Loved it! Loved it! We fully enjoyed the convenience and comfort of "Cool Breeze" and its location. The house became our home for 6 weeks, and we hated to leave. Even had the chance to meet the owner, who was more than accommodating. The icing on the cake was the property manager, who made sure our stay was the ultimate vacation. Would definitely return for another 6 weeks (or more).

Janice B, 02/01/2013

A Perfect Week!

Our stay at Cool Breeze was fantastic!  We stayed for a week and had a great time. The place was immaculate upon our arrival. And it was furnished with everything we could have wanted. The location could not have been more perfect. Just two blocks from Duvall Street in one direction, two blocks to the entrance of Ft Zachary Taylor State Park in the other and about a 10 minute walk to Mallory Square to the north or 10 minutes to the Southern Most "everything" to the south. When we weren't out seeing sites, enjoying a meal or just taking in the culture we relaxed at pool side just out the back door. Lori provided "concierge service" that made the trip hassle-free. She made reservations, secured discounts and even had bicycles delivered to our front door. The combination of accommodations, location and service resulted in a TRULY FIVE STAR experience! THANK YOU!!

Ron B, 12/30/2012

Wonderful Home, close to everything

The house was wonderful!!!!! Very clean and had everything we needed. Enjoyed the front porch for people watching and the back porch for morning coffee or an evening drink. It is close to Duval St. and all the things going on. We went to Key West for the Power Boat races, and this was the ideal place to stay for that also. I would recommend this home. Thanks to Lori for the "Happy Birthday" signs for Rick.  That was a great extra touch! I want to wish John and Janine best wishes in this venture. Thanks for letting us rent it! 

Rick and LouAnn

Louann E, 11/06/2012

Best Villa in Key West! Great Location!

We are two couples over 50 who love to travel. This is the best Villa in Key West! First, it is so bright and cheerful with lots of room, 2.5 baths, kitchen with everything you need, glasses, dishes, pots and pans for eating in, extremely comfortable furniture and beds, a dining table inside and out on the back patio. The villa is so quiet that if three of us were downstairs listening to music and laughing and one was napping, they never heard a thing! Amazing! We rented bikes and there is plenty of room to keep them in the fenced back yard, there is also a balcony off of the master bedroom that looks over the community pool so you can scope out a chair before you walk out your back gate to the pool! The beach is a short walk or bike ride away and Blue Heaven and the Green Parrot are within 2 blocks! You are two blocks from the main party street Duval and walk right in the center of the action! Last but not least Lori Bailey is the best! She made our trip perfect, she was available for anything you needed or any questions and we cannot wait to come back to Cool Breeze! Thank you Lori!!!

Tamra C, 10/22/2012

Perfect Location in the Heart of Key West

This is absolutely the best location in Key West. You are on a secure, private street in Truman Annex, yet one block from all the action. It was so nice to be able to come home and relax in the serenity of Cool Breeze after an adventure filled day exploring Key West. The home itself was perfect for us. The home was very clean, and was fully stocked with everything we needed for our trip. I would highly recommend this home for anyone looking to stay in the heart of Key West, but wanting a little more peaceful setting to relax at the end of the day. I couldn't end this review without mentioning Lori Bailey at Last Key Realty. Lori is awesome!! She welcomed us at the house upon arrival, and was there to answer all our questions throughout the entire vacation. She booked discounted reservations for us with multiple vendors, and was always extremely professional, happy, and generally made our trip perfect in every way.

Jack S, 07/13/2012


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