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Last Key Realty

Member since: 2005
Call Manager
Speaks: english, french

:: WINDOWS ON THE GULF @ THE ANNEX :: Oceanfront / Luxurious Penthouse / Pool...

Bedrooms 2
Half Baths1
Property type condo
Minimum Stay 6 nights

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Truman Annex Condo Rental Photos and Description

Oceanfront 2BR/2.5BA Penthouse Condo with Pool & Cabana, next to Mallory Square

Directly facing the Gulf of Mexico right next to Mallory Square, this beautiful penthouse condo 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 this home are over-sized, with 10 foot ceilings and elegant overhead fans.


The master bedroom 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.


As a Vacation Rental Broker, we will do everything possible to assure you of a memorable and thoroughly enjoyable stay while you are in one of the homes we manage. Our job is to make sure each home has been maintained to an exceptional standard and has no defects or problems that will spoil your stay. If there is a problem, we pride ourselves in our ability to address and solve that problem before it has intruded on your vacation experience.


As your Key West real estate company, (if you decide you are interested in buying real estate in Key West), we will assist you in making your dream of home ownership in paradise a reality while maintaining the highest level of integrity during the property buying process. While we are licensed to sell real estate by the state of Florida, we are also members of the National, Florida and Key West Associations of Realtors. We agree with and abide by the Realtors Code of Ethics so there is never a question of our commitment to our client.

More Details
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed
  • suitable for elderly or infirm
Last Key Realty (Property Manager)
Call Manager
Speaks: english, french


Exceptional! 5/5 -
(43 traveler reviews)
:: WINDOWS ON THE GULF @ THE ANNEX :: Oceanfront / Luxurious Penthouse / Pool...
average rating of 4.9534883 based on 43 reviews

Wonderful Property

  • 5 of 5

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!

  • Submitted: Aug 16, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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Amazing condo on the waterfront

  • 5 of 5

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.

  • Submitted: Jul 12, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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Gorgeous Condo in the heart of Key West!!

  • 5 of 5

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!

  • Submitted: Jun 12, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
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  • 5 of 5

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.

  • Submitted: Jun 2, 2016
  • Stayed: May 2016
  • Source: HomeAway
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  • 5 of 5

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

  • Submitted: May 11, 2016
  • Stayed: Apr 2016
  • Source: HomeAway
Owner's Response: 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 :)
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Charlotte, North Carolina

Paradise Found!

  • 5 of 5

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

  • Submitted: Nov 12, 2015
  • Stayed: Sep 2015
  • Source: HomeAway
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Nearest Airport
2 Miles
Key West international Airport
Nearest Barpub
0.2 Miles
The Green Parrot
Nearest Ferry
0.9 Miles
Fort Myers Ferry
Nearest Golf
5 Miles
Key West Golf Club
Nearest Motorway
0.1 Miles
Route 1
Nearest Restaurant
0.3 Miles
Blue Heaven
Nearest Beach
0.5 Miles
Fort Zachary Taylor State Park
Car: not necessary


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Truman Annex Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 3
  • Guests provide their own meals
Floor Area:
  • 2100 sq. ft.
  • 1 story
Location Type:
  • Downtown
  • Near The Ocean
  • Town
  • Village
  • Waterfront
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Ceiling Fans
  • Clothes Dryer
  • Elevator
  • Filtered Water
  • Garage ...
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking Off Street
  • Shampoo
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • 1 Half Bath
  • Second Bathroom - toilet , combination tub/shower
    Hall Bath - toilet
    Master Bathroom - toilet , shower
  • 2 Bedrooms, Sleeps 6
  • Living room - 1 queen , 1 sleep sofa /futon , Queen sleep sofa
    Master Bedroom - 1 king
    Second Bedroom - 1 queen
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • Balcony
  • Beach Towels
  • Bicycles ...
  • Gated Community
  • Outdoor Grill ...
  • Patio
  • Walkway to Water
  • 6 garden chairs
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only ...
  • pets not allowed ...
  • suitable for elderly or infirm
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • Outdoor Pool
Onsite Services:
  • Concierge
  • arboretum
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • reefs
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • gambling casinos
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing

Learn more about this vacation rental at the manager's website:

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