Windows on the Gulf

$0.00 Weekly
Unit Type: Condominium
Pets Allowed: No Pets
Address: 115 Front Street #303 Key West, FL 33040
Neighborhood: Truman Annex
Stay Type: Weekly, Monthly

Overview Read Reviews

Windows on the Gulf is a lavish 3rd floor waterfront condo, with stunning views...
There are three different seating areas in the open plan living area, all with commanding water views...
The main living area inlcudes a flat screen TV and a plush sectional sofa...
The condo has multiple balconies overlooking the Gulf, each with comfortable outdoor seating...
The dining table seats six comfortably...
There's even a bar with seating for six, for casual meals...
The kitchen has just recently been renovated to a very high standard, with unique stainless cabinetry...
All of the appliances are top-of-the-line, including the Sub-Zero refrigerator...
A convenient half bathroom is located in the hallway...
The spacious master bedroom has a King bed...
The master bedroom also has French doors that open up to the master balcony...
The master balcony is the perfect place to enjoy your morning coffee or an afternoon cocktail...
The master bedroom also has a flat screen TV and an overhead fan...
The master bathroom is en suite, with double vanities and plenty of closet space...
The master bathroom has an extra large custom glass and tile shower with double shower heads...
The second bedroom has a Queen bed and an overhead fan...
The second bedroom has a private balcony too...
The second bedroom also has a flat screen TV and an en suite bathroom...
The en suite bathroom has a shower and tub combo...
The community pool is just steps from your condo, with lush tropical plantings...
The pool is large enough to do laps and is surrounded by comfortable chaise lounges...
The pool area includes a cabana with restrooms for your convenience...
The pool has direct views of the Gulf...
You'll have your own keys to the Promenade that goes to Sunset Pier...
Fort Zachary Taylor State Park Beach is located a couple blocks away...
There are beach chair and umbrella rentals at Fort Zach...
Be sure to get out and experience the beautiful waters of Key West 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...


"Paradise Found! We absolutely loved our stay at Windows on the Gulf. We are not sure we could possibly point to one thing we loved the most. Everything was perfect! The pool, the location, the design of the condo, the neighbors and especially Shel. Shel was available via phone, text or email during our stay and answered all our questions with enthusiasm and care. We won't rent from anyone else in Key West as this is hands down the best rental experience we have had. The group before us left a book behind of the things you must do in Key West before you leave. The book allows you to tick things off the list. We marked a few things off the list, but the group before us definitely had a great start. If you stay here you should look for this book. It definitely added a personal touch for us." - Tiffany A. 09/15


Directly facing the Gulf of Mexico right next to Mallory Square, "Windows on the Gulf" is the perfect place to spend your stay in Key West. With panoramic views of the water and cruise ships as they dock nearby, you'll be tempted to just sit out on one of your breezy balconies and just take in the sights. But this sumptuously furnished home has its temptations, too.


There are three different seating areas in the open plan living area, all with commanding water views. The kitchen has just recently been renovated to a very high standard, with unique stainless cabinetry that has to be seen to be appreciated. All of the appliances are top-of-the-line, including the Sub-Zero refrigerator. There's even a bar with seating for six, for casual meals. If you are forced to work while you're here, you'll be glad to know that even the home office has a water view. All of the rooms in "Windows on the Gulf" are over-sized, with 10 foot ceilings and elegant overhead fans.


The master bedroom in "Windows on the Gulf" has everything the 'master' might want: king bed, French doors to the sundeck, flat screen TV, walk-in closets and a private balcony with water view. The en-suite master bathroom is unique, with a custom glass and tile shower with double shower heads. There are, of course two vanities. The second bedroom has a queen bed, its own balcony entrance, and an en-suite bathroom. If you have extra guests, one of the sofas in the living area will convert to a queen bed. A powder room in the hall is an added convenience for your guests. You'll have 2 off-street parking spaces in the garage.


The Community Pool is right downstairs, located directly on the Gulf of Mexico. There are plenty of chaises and dining sets with umbrellas for your comfort, and a cabana with restrooms for your convenience. You'll have your own keys to the Promenade that goes to Sunset Pier.


Central Heat and A/C, Ceiling Fans, High Definition Cable TV, DVD Players, Microwave, Blender, Toaster, Gourmet Kitchen, Linens and Towels provided, Assigned off-street parking for 2 cars. Daily or weekly housekeeping provided upon request. Wireless high-speed Internet access. This property will accommodate up to 6 adults, and is completely non-smoking both inside the unit and on all balconies.


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Map may not be 100% accurate.


  • Area - Truman Annex
  • Property Type - Condominium
  • Bedrooms - 2.00
  • Sleep Cap - 6
  • Rental License Period - Weekly, Monthly
  • Approx Sq. Ft. - 2060
  • Complex - Harbour Place
  • Pets - No Pets
  • Parking - Off-Street - Garage
  • Waterfront


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


  • Number of Bathrooms - 2.5
  • Bathroom 1 Size - Full
  • Bathroom 1 Type - Shower Only
  • Bathroom 1 En Suite
  • Bathroom 1 Floor - First
  • Bathroom 2 Size - Full
  • Bathroom 2 Type - Shower/Tub Combo
  • Bathroom 2 En Suite
  • Bathroom 2 Floor - First
  • Bathroom 3 Size - Half
  • Bathroom 3 Type - None
  • Bathroom 3 Floor - First

Indoor Amenities

  • Sleeper Sofa - Queen
  • Sleeper Sofa Mattress - Standard
  • Elevator
  • Dining Room Seats - 6

Outdoor Amenities

  • Pool - Community
  • Heated Pool
  • Grill - Prohibited by Fire Code


  • Living Room TV - HD
  • Living Room DVD - Standard DVD
  • Surround Sound

Recent Reviews About This Property

Our stay in Key West and in Windows on the Gulf was perfect!

My husband and I take a vacation every year with my sister and her husband to celebrate mine and my sister's birthdays. Shel Segal and the staff of Last Key Realty helped to make our birthday vacation extra-special. Shel went above and beyond to help me and my sister provide birthday surprises for each other. Shel also met us upon arrival at the condo, explained everything and was always available to help us in any way we needed. We especially appreciated his local perspectives on restaurants and things to do. We were all very happy with his recommendations of the restaurants we tried. In addition, we loved the condo. It was very spacious yet cozy, convenient to Mallory Square and other locales, clean and had a wonderful view of the gorgeous sunsets. All in all, our vacation was perfect. We highly recommend working with Shel and Last Key Realty if you want an exceptional experience in Key West.
Diane D from Cleveland, OH, 05/12/2018

What a wonderful family vacation we had at Windows on the Gulf!

We celebrated my husband's 60th with our family which included our 6 month old grandson. The lay out of the condo and upscale furnishings provided privacy and pampering! And the views from the balconies--breathtaking! We loved the location of this condo in the Truman Annex. Just a short walk to Mallory Square but away from the hustle and bustle. Shel from Last Key truly made us feel welcome; not only with a delicious Key Lime Pie but a ride to the grocery store! Last Key's customer service was excellent; providing us with a resource for renting baby needs and answering all of our many questions. I highly recommend them if you plan on renting in Key West.

Kathy C, 04/28/2018

Awesome Time

Everything went great! Shel was a huge help telling us about the ins and outs of the Island and which places to check out. The property was well kept and and clean. No complaints about anything. My friends and I had a terrific vacation and we will definitely be coming back soon!

Nick S, 10/11/2017

Another stay in paradise

This was our second year staying at this remarkable condo! We vacation in Key West every year in October for our anniversary with another couple. This gorgeous property allows plenty of space for us to stay together but still have the privacy we need. Some of the highlights of the condo: The most comfortable beds and bedding, unbelievable modern bathrooms for each bedroom as well as a half bath, washer and dryer, 3 balconies, view of the cruise ships coming in and out, beautiful modern kitchen with all the appliances one would need, great pool and a short walk to all the Duval hotspots. Not to mention it has the best sunset views on the island. We watched from Sunset Pier one night during our stay and decided our third floor balcony was even better! Nothing like a cocktail in your hand, your feet up on the railing and a completely unobstructed view. This year, Hurricane Irma had us making alternate plans. Even when we found out Key West would be accepting tourists, we wanted to be respectful of the residents who were picking up the pieces of their lives. Shel from Last Key Realty assured us that we would be welcomed by the locals. He even arranged for us to check in two days earlier when our Islamorada hotel was damaged. And, he was right. The locals seemed to really appreciate that we were there to bolster the economy. Shel accommodated our check in time request as well as our request for a little bit of a later check out. And, we had a delicious key lime pie waiting for us in our fridge! Little touches like that make all the difference in the world. We had another wonderful vacation thanks in no little part to Shel and Last Key Realty's wonderful rental. We'll see you next year!

Denise E, 09/28/2017


I stayed at the Windows on The Gulf in September 2017. This place is breathtaking. The hotel has panoramic views of the Gulf of Mexico. The rental is situated in a perfect location close to the action but far enough to have privacy and tranquility. Shel was beyond helpful and went above and beyond to please our every need. Everything was perfect when it came to the place, location, and service provided by Shel. I had to cut my trip short due to hurricane Irma which was unfortunate. However, Shel was knowledgeable with the safety precautions we should take and what steps we need to take before, during and after the storm. I strongly, without any reservation, recommend Windows on the Gulf!!!

Monika K, 09/02/2017

Sunset Bliss

Windows on the Gulf is a top notch property. My family of four stayed for a week. The condo is comfortable, relaxing and clean. Close to the craziness of Key West but well located and quiet. The sunsets from the balcony can't be beat. Shel the property manager is so helpful, available and a dear of a man. Just do it.

Valerie T, 08/05/2017


We stayed for a week and could not have been more pleased! The property was fantastic! Well located, spacious, clean with unbelievable sunset views! We moored our boat directly behind the property in the marina. We were walking distance to everything!

Steve K, 07/21/2017

Great place to stay.

Very nice. Well maintained. Great location. Management team was great and Shel went out if his way to help us with a special package delivery for my dad for Father's Day. We would definitely go again.

Dan M, 06/16/2017

Perfect vacation!

We had a great time in Key West. Shel was awesome. Greatest hospitality we have ever experienced renting a vacation property.
Stephanie B from Slidell, La, 06/05/2017

Fabulous Condo!

Extremely nice condo in quiet area yet close to all of the action. This is a gated community for additional security with security patrols. Fabulous views from three balconies with lots of natural light through many windows. Well appointed condo with everything you need available. Top end kitchen appliances. Concierge service available. I highly recommend this unit!

Donald S, 09/18/2016

Absolute Perfection

I highly recommend this rental. The views are breathtaking and the condo is superb. Any amenity that you would ever need is thought of and so much more. Shel Segal is an extraordinary property manager. He was super responsive and made recommendations on things we did not even consider, but were wonderful additions to our trip. He is one of the most customer-centric managers I have ever had the pleasure of interacting with. I travel weekly for business and have never had such an incredible experience. I am already planning our return to Key West and will absolutely work with Last Key Realty.


Tammy L, 08/28/2016

Could do no better

Superb clean apartment, with the ocean and city center just meters away. A large well appointed apartment, with a kitchen that has everything. The apartment has two covered parking spaces under the building. Shel was there at arrival ensuring it went smoothly; he has a wealth of knowledge on restaurants, bars, and activities. I would recommend this apartment to a relative or friend without hesitation

robert w, 08/04/2016

Wonderful Property

Our family of 4 had a fabulous stay at this property for a week in July! It is convenient to everything in Old Town. Rented bikes and rarely used our car. The property is lovely and the views with sunsets from the balcony are stunning! No fighting for chairs at the pool and the best part of this rental is the property manager Shel! He was very personable and took care of our every need. I highly recommend you take his recommendations on dining which he will leave you a nice list of restaurants for all kinds of dining/food. I'm a bit of a foodie and his recs were spot on. Lovely rental! We will be back!

A guest from R, 07/10/2016

Amazing condo on the waterfront

My husband and I stayed here with another couple last week. The unit is beautiful and high end. It had everything we needed to enjoy a week in Key West. Shel met us at check-in and made sure we had everything we needed for the week. He even purchased a Keurig coffee maker for the condo so I could have my morning fix. The list of restaraunt recommendations made by Shel was really helpful-we tried almost everything he recommended and could not have been more pleased--the food is amazing on the island. The condo is located just around the corner from Mallory Square and Duval Street. You can't go wrong with this rental.

Kelly O, 07/03/2016

Gorgeous Condo in the heart of Key West!!

Pictures don't do this property justice. Absolutely beautiful with spectacular views and easy access to all Key West's attractions. Last Key Realty does a superb job of maintaining the property, orienting guests, and arranging tours. Shel took care of everything to make us feel welcome and the concierge staff found tours suited specifically to what we wanted--like the sunset cruise just for the 4 of us. This property and Last Key Realty gave us a vacation we will never forget!

Amy G, 06/09/2016


This place was amazing. Exactly what we imagined for our wedding week. The location was within walking distance to everything and the views are breathtaking.

Paige C, 05/16/2016


Great property great location. Only suggestion would be to make mid week cleaning services available.

Kim A, 05/01/2016

Response from Last Key Realty:

We are so happy to hear Kim had a great time at Windows on the Gulf. There may have been a miscommunication unfortunately, because we DO offer interim cleaning, as often as every day if requested! Shel (and all of our Guest Services Coordinators) offer this service to be scheduled prior to arrival, and can also accommodate requests while in residence. Any guests who desire interim cleaning simply let us know and we will arrange any services you request. Kim, on your next visit we hope to clean for you as often as you'd like :)


The Perfect Vacation

Luxurious accommodations. Perfect to have two master suites! Amazing sunsets from our spacious balcony. Excellent location to take advantage of everything Key West offers. Shel was the perfect host. Recommended restaurants and venues were excellent. Would not hesitate in the least to return!


Claudia M, 10/04/2015

Paradise Found!

We absolutely loved our stay at Windows on the Gulf. We are not sure we could possibly point to one thing we loved the most. Everything was perfect! The pool, the location, the design of the condo, the neighbors and especially Shel. Shel was available via phone, text or email during our stay and answered all our questions with enthusiasm and care. We won't rent from anyone else in Key West as this is hands down the best rental experience we have had. The group before us left a book behind of the things you must do in Key West before you leave. The book allows you to tick things off the list. We marked a few things off the list, but the group before us definitely had a great start. If you stay here you should look for this book. It definitely added a personal touch for us.

Jim, Tiffany, John & Bev


Tiffany A, 09/26/2015

Best Place on Key West!

This place is amazing! The windows all face west so we never missed a sunset. We also had the pleasure of seeing cruise ships come in and fishing boats go out as we sat comfortably on our balcony. The place itself is very spacious, beautifully decorated, and immaculately clean. It is located extremely close to everywhere we wanted to go on Duval street - everything is withing walking distance. We will be sure to try and secure this place again if we are fortunate enough to go back to Key West!

Sean & Cindy J, 09/19/2015

Could not have been better!

The apartment is large, elegant, well-equipped, and spotless. The location is prime and the views are outstanding. It is close to all the action but nestled in a private and quiet enclave. We had excellent, personal service and support from the minute we booked the property until the hour we departed. The concierge helped us find the best excursions for dolphin watching, kayaking, snorkeling, boating, and fishing. We felt like royalty!

mary lou m, 09/05/2015


From the moment we walked in until we closed the door for the last time, we loved our time at Windows on the Gulf. Words won't adequately describe how relaxing, beautiful, and well appointed this property is.

The condo is stunning with views that cannot be topped. We spent hours on the balcony overlooking the marina. Up early for astounding sunrises and most evenings found us relaxing with a drink as we watched the sun set straight out from the balcony.

The kitchen had everything we could want. We ate breakfast and lunch in the condo and several dinners out at some wonderful restaurants. Our favorite dinner was the night we grilled dinner for ourselves. Shel, our AMAZING guest services coordinator told us where to shop for the best fresh fish, and directed us to a wonderful market within walking distance.  Fresh fish (try mutton snapper if they have it,) asparagus and red potatoes were grilled on the patio and we set the table for four on the side balcony. Absolutely wonderful meal and ambience. It just doesn't get better!

Both bedrooms were well appointed and comfortable. The huge shower in the master bedroom included three different shower heads. 

The three sitting areas were perfect and comfortable.

The pool area was very nice, secluded and quiet. We enjoyed using the floats provided to laze away our afternoons on a couple of occasions.    

The location of the building is quiet and peaceful.

Shel provided top-notch service from the moment we reserved the condo to the moment we stepped into the taxi to leave for the airport. 

The location was incredible. Whether walking out the front and down the street or out the gate onto the walkway to Mallory Square, you didn't want for anything. No need to rent a car at all! We rented scooters to get around and see the sites. So much fun. Restaurants, shopping, and excursions (we took the wind, wine and sunset sail one night - a MUST DO) within steps or just a few blocks. 

Next time we are in Key West we will definitely work with Shel and Last Key Realty. The service couldn't have been better and they have several wonderful properties from which to choose, although this has been our favorite rental to date.


Jeannie S, 08/22/2015


The unit was beautiful and exactly as it was pictured online. The view was incredible! The unit was very clean upon arrival, and was stocked with everything you may need. It was very close to everything. We walked and/or biked to everything we did, Duval Street, boating trips and many restaurants.  The Zachary Taylor State Park and beach was only a short bike ride away as well. Although the pool area was nice, we wished that it was as beautiful as the unit. Overall it was a very nice place, and Shel was very nice and fantastic to work with.


Todd N, 08/01/2015

Excellent in every way

First class penthouse condo. Fabulous location, on the water, 3 cruise chips docked during the week we were there. Close to Mallory Square, excellent dinning and shopping. Service from Last Key was first class in every way. Sehl, Fiorella, Thomas and everyone else I talked to went out of their way to help Sue and I enjoy our stay.

Jerry L, 06/27/2015

Beautiful view, great location, & clean!

Shel was extremely helpful to recommend restaurants and show us around the condo property. The condo is in a terrific location. And, it was CLEAN!

We will be back!!


Susan B, 06/20/2015


A gorgeous penthouse condo with wonderful ocean views. 2100 square feet of pure luxury. We will definitely be back. Our guest services director was fantastic. Very pleased!

Douglas H, 06/13/2015

Most Gorgeous Place in Key West

One of the most beautiful properties in Key West. I used to live in the Keys and had oceanfront property and this condo with its incredible views, designer furniture and style had it beat.  It's even more beautiful than the pictures. Close to Duval so you can walk everywhere. Classy, elegant. Shel Segel the property manager was very helpful and coordinated our arrival and departure seamlessly.  We will be returning as we have before to Windows on the Gulf.

Heidi L, 06/01/2015

Beautiful condo and fantastic view

Great location, fabulous sunset views, good parking. Beautiful, well appointed, equipped and comfortable condo, very complete kitchen, lovely bedrooms and master bath. Great customer service. Property manager Shel, was most helpful and cooperative, working to make sure our stay went smoothly. We would definitely recommend this property.

Marylyn W, 09/27/2014

Absolutely Beautiful

My husband and I stayed a week with another couple to celebrate our anniversary. The condo is in a great location and has beautiful views. The bedrooms and bathrooms are spacious and nicely decorated. The kitchen has everything you need. Shel, the property manager was helpful and courteous. We would so stay there again!

Debbie D, 09/20/2014

Beautiful and Spacious

Four of us (2 couples) stayed at this condo for a week and absolutely loved it. It is beautifully decorated, well stocked, and the lay out is perfect for couples with the 2nd master tucked away in the back. It was very clean and comfortable with beautiful sunset views. We cooked in a couple of nights and found everything we needed. The balcony is perfect as it is hidden from neighbors by a palm tree. The location is perfect, right in Truman Annex within easy walking distance to Mallory Square, Duval Street, Hemingway House, etc. Perfect! Shel was great and the concierge service was very efficient, friendly, and helpful. We used them to book some restaurant reservations and reservations on the ferry to the Dry Tortugas.


vanessa m, 09/13/2014

Great condo in a great location!

My wife and I spend a week at Windows on the Gulf with another couple to celebrate a birthday. The Condo was "top of the line" with an excellent view and a modern feel.  The bedrooms were seperated from each other which made sharing the condo with another couple very easy.

Shel with Last Key Realty was a pleasure to work with, very accomodating and informative.

We hope to be back soon!


Todd O, 09/06/2014

A very unique and accomodating property

Our family had a wonderful time. This is the 3rd year we have rented Windows and every time the property is first class, our guest service individual (Shel) and Chris and his team at Last Key have been great. We use our stay at Windows as a relaxing calm prior to the launch into an always busy school and professional year. We plan to be back.

Andrew R, 08/09/2014


There is nothing bad to say about this property. Location was perfect. The condo was immaculate. We had the best trip possible and can't wait to come back again!

Vince M, 07/26/2014

Wonderful accommodations!

We loved staying at the Annex. It was spacious, modern, and very comfortable. The view was great, we spent many nights on the deck watching the sun set. We are really looking forward to coming back!

Anonymous , 07/15/2014

Review of Windows on the Gulf

Great two bedroom condo. Location was very quiet and peaceful. Naval station is close to Duval street but very private. Kitchen was very well stocked and quite modern. Views of the harbor were outstanding. We loved this unite and would highly recommend it.

Albert T, 07/08/2014

Perfect Peaceful Private Pleasure Palace!

Our family of four stayed at Windows on the Gulf for about a week and absolutely loved it. 

The photos on the Last Key Realty website were great, but the actual experience from walking in to walking out was more than we could have asked for...except walking out...we didn't want to do that!

The quality of this property, the amazing views and the terrific service from our personal property manager, Shel Segel, along with the entire Last Key Realty team made our stay absolutely wonderful.

The Truman Annex area is a great place to stay if you are looking for a place that is close to, but just off, the beaten path and it's proximity to Mallory Square, Old Town, Duval St, the beaches and other sites is perfect...we barely had to drive, which made staying in Key West much more peaceful.  The history of this location comes alive and you feel like you are a part of something special by residing where Presidents stayed during their tenures.  The Truman Little White House is about 50 steps out the front door and a wonderful tour to take during your stay, like I said, the history is amazing here.

I've already made recommendations to our friends and we are planning to stay here again next year for our family vacation.

We would live here if we could!


Jason P, 06/26/2014

Amazing stay!

It was an amazing stay right from the condo to the service we received. The condo was ideally situated, we loved that the condo was well stocked with utensils, towels etc. The description of the property and the photos are spot on. The kids enjoyed the convenience of the pool; basically it was like a home away from home and worked out perfect for us. Shel went above and beyond with accommodating our last minute requests to suggesting places to eat. Overall a 5 star experience and we would definitely go back again!


Kim P, 06/14/2014


Perfect place to stay in Key West. View is amazing, you look right out onto the Gulf. Cruise ships do block the view a bit, but they don't stay long. Close to Fausto's for food and beverages. Shel is the best!  When our luggage was delayed he offered to get it for us if the airline didn't deliver. The cleanliness was also wonderful, the condo was spotless!  Would return in a heartbeat. Make note the pool is saltwater and much easier on your skin than a chlorinated pool. All in all one of the best vacations we've ever had!


Christina R, 05/24/2014

Great views, wonderful property!

This was our second month-long stay at "Windows on the Gulf" and it was even better than the first! Truman Annex is an extremely well maintained property with private streets, security and beautiful landscaping. Huge old palm trees and wonderfully historic buildings. The condominium is beautifully decorated with all the modern conveniences and appliances. Great kitchen, and brand new washer and dryer! Also, palm trees out every window.

The best thing about #303 is the view of the harbor and the Gulf of Mexico. Sunset viewing from the balcony was one of our favorite things to do. Do not be dissuaded from staying here because the main balcony is on the west side and is not covered/shaded. We sat out on the balcony almost every evening and enjoyed the sunset and boats crisscrossing the gulf. Because this is a penthouse unit, and Key West is a very low island, you are able to catch a nice breeze almost no matter what the wind direction.

We travel extensively and stay in similar properties across the U.S. and around the world. "Windows on the Gulf" is one of the nicest we have experienced; I would stay here anytime our schedule permits.

Finally, Last Key Realty is a first class vacation rental/management company, and Shel, the guest services coordinator, is the best. He will quickly and happily take care of anything you need.

I highly recommend this place.


Ron W, 04/20/2014


Windows on the Gulf is the perfect place to stay in Key West. We have been several times and this was by far the best. Absolute luxury in a perfect location - close to everything. We were a family of 4 which included 2 teenagers and the condo was exactly what we needed - spacious and yet private enough for each of us. And the views - WOW - the photos do not do it justice - just breathtaking! They were re-landscaping the grounds during our visit so I'm sure it looks fantastic now. 

To me what stands out more than the luxury was the customer service provided by Last Key Realty. Reservations were a breeze and Shel was amazing - he checked in with us several times before and during our stay. We had one minor issue with the hot water and he had a plumber there in 10 minutes - no kidding!  He took great care of us and treated us like family. I am so spoiled now that I can't imagine staying anywhere else in Key West - we will definitely be returning!


Morgen S, 06/16/2013

Response from Last Key Realty:

Thank you for this wonderful compliment. We are thrilled to hear the condo was even nicer than you expected from the photos, and that you thoroughly enjoyed your stay with us in Key West. What we are most proud of is your feedback about the service you received. Shel and the rest of the Last Key team aim to make your reservations, arrival, and stay as smooth as possible and to hear that a potential issue with the hot water was resolved immediately confirms that we are doing our job as your Guest Services Company. We look forward to your next visit to "spoil" you some more!


Elegantly furnished and incredible view.

This property is a gem. I used to live in the Keys and returning as a guest was a pleasure because I could entertain in style and have a beautiful view. Shel, the property manager was a pleasure to deal with and renting it was easy. I am planning on returning and making this an annual event. You will not be dissappointed with this property it exceeded my expectations.

Heidi L, 06/01/2013

Response from Last Key Realty:

What a compliment to hear that a previous local of the Keys was so pleased with a stay in Windows on the Gulf. It is true that this condo is perfect for entertaining in style, with a view that serves as the ultimate backdrop to a get together with family and friends. We look forward to having this guest back annually for many more great stays in Windows on the Gulf.


Great Harbor views, very luxurious.

Windows on the Gulf is one of the most luxurious places we have ever stayed. The views of the harbor were the main attraction for us, but the quality and size of the unit itself were very impressive. We stayed for one month and completely enjoyed the large kitchen, spacious living/dining area and the office area [an unfortunate necessity] was very useful. The multiple balconies make sitting outside possible at different times of day and the sunset filled the windows every afternoon; absolutely beautiful! The pool area is very private and clean. All of Harbor Place, and Windows on the Gulf in particular, are very well maintained and secure. Harbor Place is in a great location for easy walking to the great restaurants and bars of Key West. The guest services guy, Shel, was very accommodating and helpful; very nice about delivering our mail. We have already made arrangements to return next year, that says a lot!

Ron W, 04/07/2013

Windows on the Gulf

My husband and I stayed at “Windows on the Gulf,” in Key West. The property was more than we needed, but we thoroughly enjoyed vacationing in luxury. The property is absolutely beautiful, immaculate, and in the perfect location. We are now spoiled, and will never be satisfied with a hotel. It is close to all the action, yet it is quiet at night and has good security. In the past we have stayed at the other end of Key West which was nice, but this we loved. You are right on the boardwalk so you can enjoy Mallory Square or you can just enjoy the sunset from your veranda…or because you are right there, you can do both…location, location, location. All along the boardwalk there are many boutiques, restaurants, bars, and music. There is always something to do and a great way to spend every evening without having to plan specific activities. We stopped to eat at a spot along the boardwalk and ended up staying for hours to listen to the Doerfels, a very talented musical family of about 10 siblings. We would go out of our way to see them again, they were that good. Now, for Shel. He contacted us before we even arrived to introduce himself, and to help us with any activities/planning. If you book an activity through him, I believe you will get a 10% discount, which helps a little as many activities are quite expensive. Shel met us at the condo when we arrived to welcome us and show us around. He even drove us to the grocery store to pick up some supplies for the week. He helped arrange a fishing excursion (we never fished before) with Red Bull Charters which was a lot of fun. The Captain cleaned the fish we caught. We then took it to a restaurant and they prepared it for us. What fun! We rented hybrid bikes for the whole week, which we loved. We ended up biking more than we thought we would especially because the bikes were so great. Even though you can walk most everywhere, sometimes there is so much you want to do that walking takes up too much time. Or like us, you have several favorites on opposite ends:  you can(must) breakfast at Blue Heaven, beach at Fort Zachary, drinks at Louies Backyard, back to the boardwalk for sunset…you get my drift. We will definitely be returning!


Rita G, 12/09/2012

Doesn't get any better than this!

Your condo is fantastic!!!!! We really enjoyed our week stay over Thanksgiving and appreciated everything the condo unit had to offer. Everything we could have wanted was in the condo...and more! The appliances were excellent, the beds were comfortable, and the bathrooms were amazing. The furnishings were first rate! There were five of us staying in the condo and there was more than enough space! We enjoyed sitting out on the deck in the evenings to watch the beautiful Key West sunsets. We used the pool everyday, and some of the time, we had the pool all to ourselves which was a treat!  Pool was never overly crowded and we met some nice people. Having the two parking spaces in the garage was very convenient. We really appreciated Shel, the property manager, checking us in and helping us to get settled. He gave us the tour and recommended places to visit and eat. He was more than helpful! We took the Wind and Wine Sunset Cruise ( one evening, and to our amazement, the boat dock was conveniently located right across the promenade from our condo. We highly recommend the cruise. We had a WONDERFUL stay at "Windows on the Gulf" and would love to vacation here again in the future!  Thank you.



Andrea S, 11/20/2012


Windows on the Gulf, was great. There is plenty of room to move around and plenty of seating. The condo is in a great location, close walk to pretty much everything. Shel, guest services, was great he was very concerned about all our needs.

Lisa D, 11/03/2012

Wonderful Vacation Condo

Great place to stay! So handy to everything! Shel the manager was very knowledgeable and helpful. The view was out of this world and I could never tire of having the cruise ships pull up in our front yard! No need to take the sunset cruise, we had a front row seat every night. I would stay here again for sure!

Kerrin K, 10/12/2012

Windows on the gulf

WOTG was great, it is a spacious 2 bedroom with great views, although the balcony's were a bit small. The pool was great and was only a short walk to many attractions. All in all we really enjoyed the stay, we look forward to visiting again.



Steve b, 09/08/2012

Windows on the Gulf

Wonderful, wonderful was our stay at Windows on the Gulf. It was as pictured and so, so much more. Shel, the property manager, was very helpful, not only with the condo but also giving us information about places to eat and other activities. The location was perfect for everything we wanted to do. We were already planning our next trip to Key West before we left. Thanks again Shel.  

The Blacks and The Stevens

North Carolina


Doralene Harris B, 08/18/2012

My favorite getaway...

I always enjoy my stay in Windows on the Gulf. I look forward to unwinding in this lavish well appointed condo In the Truman Annex. It is so close to everything but quiet since it is located in the exclusive Harbour Place. One of its best features is the views. We enjoy watching the Navy and cruise ships as they come into port at Key West and the sunsets are spectacular from the balconys. Whether you prefer to entertain at home or go out to enjoy the night life on Duval Street, this condo has it all. The pool is also one of the finest on the island. If you need anything, Shel is the go to guy. I can't wait to return again.

Florida native , 08/04/2012

Windows on the Gulf @ the Annex

The condo is immaculate and the view is beautiful. The location is perfect - just a few walking minutes away from restaurants and shopping.  The condo is furnished with many sofas and chairs for everyone to feel as if they have their own space. The balconys are a great getaway as well! Shel, our Guest Services Manager is more than accommodating.  We have been to Key West many times and found his services and our accomodations far superior to other stays.  The price is right for a 2 bedroom, and with such a nice living room there is plenty of room for 6 persons to sleep.

Jean F, 07/15/2012

Windows on the Gulf

This is a fantastic condo unit with beautiful sunset views overlooking the Westin Marina and Sunset Key. The unit is beautifully decorated and very well equipped. This kitchen is top notch. The unit is convenient to Mallory Square and Duval Street, though very quiet and safe. We really enjoyed our stay here, and the property manager Shel is a great guy! We will return!!!

Ryan M, 07/01/2012

Just Perfect

Everything about this place was great. Starting with Shel, the property manager, who helped us with anything we needed. He showed us around the condo, recommended some places to go and was only a phone call away for anything else.

The unit had everything you wanted. Updated kitchen with every applicance you would need.  Lots of room to spread out, big closets, nice sized bedrooms.

The location is excellent! You can have privacy if you want but Duval St is not far. The view of the sunset is unbelievable. We usually go to Mallory Square to watch it, but stayed right at home a couple nights and had the perfect view.

I would highly recommend this place, a real gem! Honestly, we didn't want to leave, and we are already planning a trip next year.


joann f, 06/16/2012

Excellent Vacation

Over the past couple of years my wife and I have traveled to many different places with friends. This has proved to be one of the best. Shel did an excellent job helping us enjoy our vacation. He took the time to recommend places to eat and exciting things to do. He was just a phone call away if there was anything we needed. We would highily recommend windows on the gulf. PERFECT LOCATION for anything you would want to do and a BEAUTIFUL place to enjoy vacation.

Lacy F, 06/09/2012

Absolutely wonderful stay. 1st Quality building

Upon our arrival, the house mgmt firm, led by Shel took the time and effort to meet us at the condo. He showed us through the condo, pointing out switches and amenities. He also helped us unpack from our long drive and then spent even more time to go over the list of restaurants in the area with details of each menu. The home is very clean. The furniture, bedding and kitchen and bath are all high end. It more than met our expectations. The view from the porch of the sunset was beyond therapeutic. now about the are on front street. You can get to Mallory square in about 1 min. Duval in about 3 min. The pool is well maintained, clean and the built in jets made it very much a hot tub. Our only regret is not spending more time there. If you are a city person... Give yourself an extra two or three days to decompress! And yes there is good cell reception and wifi if you need to stay leashed to the outside world!


Andy P, 04/17/2012

Wonderful Windows on the Gulf

We were the first to stay in this magnificent condo. It is beautifully appointed without being fussy and we didn't lack for anything. I must say we completely enjoyed our vacation being spoiled by all the amenities of this oceanside condo and building. We look forward to our next stay!

Florida native , 04/16/2011


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