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WELCOME TO
“THE BEST OF KEY WEST”

You'll find our friendly staff and low rates among
"The Best of Key West". Use our online booking option or call us toll free at 1-800-884-7368

PLEASE NOTE ALL RESERVATIONS ARE CONSIDERED REQUESTS ONLY UNTIL YOU ARE CONTACTED BY ONE OF OUR AGENTS. You will be contacted by one of our friendly reservationist within 24 to 48 hours in order to re-confirm pricing and reservation dates.

Note: All of our properties have a maximum occupancy, please do not plan large parties, or plan to exceed the number of people allowed in each home. If you plan to have a large gathering or have additional guests please let us know in advance in order to avoid any difficulties.


Because of our wide variety of properties minimum stays may vary depending on the property you select. If you have booked a property for less than the minimum stay required we will contact you to finalize your reservations.

"RELIABLE DIRECTION
IN ANY WEATHER"

Truman Annex boasts a private gated community with 24 hour security. We have numerous luxury properties for your vacation needs. All properties require at least a 7 night minimum and book SAT to SAT in season.

Pets are welcome for a stay of 1 month or longer in the areas of Shipyard, President's Lane, the Foundry and many of the Private homes. All pets must have the approval of the property owner and be registered with the Homeowner's Association.

Coral Hammock, Oceanside Marina and Beachside Resort Condominiums may take a 3 night minimum, while the Golf Course properties are limited to monthly only. Please contact us for pet policies in these areas.

We will contact you to finalize your reservation. Rates are not guaranteed until the contract is sent out.

Compass Realty knows that in this uncertain world every bit of confidence in spending is appreciated. For your benefit Compass Realty offers travel insurance for every reservation. If you wish to accept this optional insurance simply initial the reservation agreement to authorize the addition to the rental amount.

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  1. Annie's Hideaway

    Annie's Hideaway
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    rental

    Annie's Hideaway in the Truman Annex

    This charming one bedroom, one bath 2nd floor property features a large covered deck off the the living room, updated bath and bedroom. The living room, which includes a sleeper sofa, is close to the kitchen, and dining areas. This lovely property is also close to the pool and and private assigned parking. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on the second level. All properties are outfitted with washer/dryer, pots, pans, towels linens, have central air conditioning, off street parking and pool access. Read more »
    Annie's Hideaway
    204-9 Southard Street
    Key West FL
    24.552364, -81.804795

  2. Blue Ocean

    Blue Ocean
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    rental

    Blue Ocean in the Truman Annex

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located ¼ mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on the second level. All properties are outfitted with washer/dryer, pots pans, towels; linens, have central air conditioning, off street parking and pool access. Read more »
    Blue Ocean
    106-5 Southard Street
    Key West FL
    24.552364, -81.804795

  3. A Pleasant Stay

    A Pleasant Stay
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    rental

    A Pleasant Stay in the Truman Annex

    Just inside the Truman Annex's main gate on Southard Street this well-appointed, one-bedroom, second floor features tropical views and breezes. Yet it's only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. A Pleasant Stay boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. You'll stroll through floral-lined lanes to Shipyard's around-the-corner private pool. And you're only a short walk from Fort Zachary Taylor and one of the Island's best beaches and walking/biking trails. This terrific property can be rented weekly and monthly- call us for more details- 1-800-884-7368. Read more »
    A Pleasant Stay
    102-11 Southard Street
    Key West FL
    24.552364, -81.804795

  4. Hemingway's Hammock

    Hemingway's Hammock
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    rental

    Hemingway's Hammock in the Truman Annex

    This is a ground floor unit with beautiful landscaped courtyard located next to pool. Original 2 bedroom unit that was converted to a large 1 bedroom with enlarged living room/ entertainment area makes this the perfect spacious unit for couples. Living room has a sleeper sofa for guests. Kitchen has been totally remodeled with new cabinets, and granite countertops. Hardwood floors, and ceramic tile thought. Parking is right in front of unit. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1 mile from one of the best beaches on the island. All properties are outfitted with washer/dryer, pots & pans, towels & linens, have central air conditioning, off street parking and community pool access Read more »
    Hemingway's Hammock
    206-3 Southard Street
    Key West FL
    24.552761, -81.804575

  5. Island Spa

    Island Spa
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    rental

    Island Spa in the Truman Annex

    This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing Ft. Zachery, on the second level complete with outdoor patio furniture and is very close to the community pool.One to two week stays, two person limit. The Shipyard Condominiums is located in the Truman Annex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The property is also located mile from one of the best beaches on the island. *NO WIFI* Read more »
    Island Spa
    620 Thomas Street #270
    Key West FL
    24.5524669, -81.8048561

  6. Marlin Blue

    Marlin Blue
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    rental

    Marlin Blue in the Truman Annex

    Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Truman Annex, Key West's most premier address, you are only a minute from the fine restaurants, shops, and galleries of Duval Street. Sit on your 40 foot veranda and cool off in the gentle trade winds as you watch the world go by. Your unit has central air, washer/dryer, updated furnishings, HDTV, queen size bed, and beautiful hardwood floors. Quiet and peaceful, your 1 bedroom/1 bath unit, is unique in the Shipyard and will be the perfect accommodation as you savor the paradise that Key West offers Read more »
    Marlin Blue
    208 Southard Street #7
    Key West FL
    24.5524169, -81.8047134

  7. Oyster's Pearl

    Oyster's Pearl
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    rental

    Oyster's Pearl in the Truman Annex

    This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard backing up to the entrance to Ft Zachary Taylor State Park, which has the nicest beach in Key West. Outdoor Grill. Read more »
    Oyster's Pearl
    620 Thomas Street #169
    Key West FL
    24.5524669, -81.8048561

  8. Royal Poinciena

    Royal Poinciena
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    rental

    Royal Poinciana in the Truman Annex

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located ¼ mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on the second level. All properties are outfitted with washer/dryer, pots & pans, towels & linens, have central air conditioning, off street parking and pool access. Read more »
    Royal Poinciena
    620 Thomas Street #292
    Key West FL
    24.5524669, -81.8048561

  9. Sand Crab Cabana

    Sand Crab Cabana
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    rental

    Sand Crab Cabana in the Truman Annex

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on the second level. All properties are outfitted with washer/dryer, pots & pans, towels & linens, have central air conditioning, off street parking and pool access Read more »
    Sand Crab Cabana
    620 Thomas Street, #269
    Key West FL
    24.5524669, -81.8048561

  10. Seagull Lull

    Seagull Lull
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    rental

    Seagull Lull in the Truman Annex

    Just inside Truman Annex's main gate on Southard Street is Seagull Lull, a well-appointed, one-bedroom, second floor, end unit with quiet three-side exposure to tropical views and breezes. Yet it's only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Seagull Lull, decorated with private art and lots of mirrored walls, boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. You'll stroll through floral-lined lanes to Shipyard's around-the-corner private pool. And you're only a short walk from Fort Zachary Taylor and one of the Island's best beaches and walking/biking trails. Read more »
    Seagull Lull
    202-11 Southard Street
    Key West FL
    24.5529541, -81.8049341
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305-292-1881 | rentals@compass-realty.com | http://www.compass-realty.com | 200 Front Street, Key West, FL 33040