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From $753 per night (USD)
VRBO
Waterfront Luxury Home with private pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $753 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR/2BA in Old Town!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $267 per night (USD)
Expedia
From $880 per night (USD)
VRBO
Spacious Waterfront 4 Bedroom Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $880 per night (USD)
VRBO
From $843 per night (USD)
Expedia
Oceanview home with private pool & lush landscaping!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $843 per night (USD)
Expedia
From $575 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry Building Discover your perfect Key West ret ...
From $575 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Quiet Conch House in Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $412 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Blue Heaven at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $211 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Oyster's Pearl at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Live steps from everything that makes Key West unforgettable. This first‑floor Shipyard condo blends comfort with island ...
From $282 per night (USD)
Expedia
From $1807 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** Compound + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1807 per night (USD)
VRBO
From $415 per night (USD)
Expedia
A LATITUDE ADJUSTMENT @ THE TRUMAN ANNEX
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $415 per night (USD)
Expedia
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VRBO
Another Day in Paradise at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Prime Old Town location meets effortless island living in this 2‑bedroom, 1‑bath first‑floor Shipyard condo. Bright inte ...
Click For Pricing
VRBO
From $822 per night (USD)
Expedia
A Sunset Breeze at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a beautiful private home located in the Historic Truman Gated Community in Old Town Key West. This beauty if only ...
From $822 per night (USD)
Expedia
From $299 per night (USD)
VRBO
A Sunset Poolside at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing first floor end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $299 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Archipelago ll at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $339 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Alhambra at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Alhambra is a charming one bedroom, one bath first floor unit with a huge outdoor deck! Shipyard Condominiums are locate ...
From $265 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Sailor's Story at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $357 per night (USD)
Expedia
From $314 per night (USD)
VRBO
AQUA OASIS at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $314 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Poolside Paradise in Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located direc ...
From $237 per night (USD)
Expedia
From $1002 per night (USD)
VRBO
Commodore's Cove - One block from Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of a home. Up to 12 can s ...
From $1002 per night (USD)
VRBO
From $2069 per night (USD)
Expedia
Commodore's Compound - One block from Duval St
Bedrooms:
7
Bathrooms:
8
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short bl ...
From $2069 per night (USD)
Expedia
From $1004 per night (USD)
VRBO
Seaport Suite - Steps from Duval Street
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Located in the heart of Old Town Key West, Seaport Suite is the ideal getaway for large groups of up to 12 gue ...
From $1004 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Seascape at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
First floor newly renovated 2 bedroom/ 1 bath corner end unit at the Shipyard Condominiums located in the Truman Annex C ...
From $298 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Tropical Vineyard at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $427 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Green Spot at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $247 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Another Three Hour Tour at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your slice of paradise in the Shipyard at Truman Annex. This charming first‑floor 2BR/1BA condo captures the ...
From $314 per night (USD)
VRBO
From $557 per night (USD)
Expedia
**MIDTOWN MOSAIC @ MIDTOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Spanning an e ...
From $557 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bed ...
From $302 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full siz ...
From $515 per night (USD)
Expedia
From $207 per night (USD)
VRBO
ADRIFT IN KEY WEST at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completel ...
From $207 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $225 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Forever Young at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $383 per night (USD)
VRBO
From $211 per night (USD)
Expedia
ABOUT TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $211 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Havana Views at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Special Price! - contact us ! Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks ...
From $211 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Sand Crab Cabana WEEKLY RENTAL 7 nights minimum!! Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
WEEKLY RENTAL - This property has the ability to be rented weekly (7 night minimum stay) all year long. Shipyard Condomi ...
From $460 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $393 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Direct Ocean View from Your Condo-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $406 per night (USD)
Expedia
From $498 per night (USD)
VRBO
Queen Emma at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located o ...
From $498 per night (USD)
VRBO
From $174 per night (USD)
Expedia
A Pleasant Stay at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just inside the Truman Annex's main gate on Southard Street, this well-appointed, very popular one-bedroom, second floor ...
From $174 per night (USD)
Expedia
From $480 per night (USD)
VRBO
ABSOLUTE KEY WEST in the Truman Annex >>Charming home with a European flair!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic award-winning gated community of the Truman Annex in Old Town Key West, Yo ...
From $480 per night (USD)
VRBO
From $741 per night (USD)
Expedia
Tropical Executive at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $741 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $577 per night (USD)
VRBO
From $809 per night (USD)
Expedia
Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $809 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Mesa House Dos - One block from Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Me ...
From $803 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $349 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Steps To The Beach And The Sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Explore Key West during the day and evenings are quiet. Nature's boutique offer you an exceptional view of key west's n ...
From $273 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Stone Throw Famous Duval Street Location-No Contact Check-In
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $267 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, ...
From $547 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $428 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Rate reduced to a off season price point. This home sits in Key Lime Grove Subdivision which I was born and raised in. ...
From $294 per night (USD)
VRBO
From $764 per night (USD)
Expedia
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $764 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $577 per night (USD)
VRBO
From $174 per night (USD)
Expedia
SUN, SEA & SKY at Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the desirable Truman Annex community, this beautifully maintained second-story Shipyard condo offers the perf ...
From $174 per night (USD)
Expedia
From $290 per night (USD)
VRBO
A Change In Latitude at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A stay in A CHANGE IN LATITUDE is more than just a rental but will be a part of your Key West vacation experience. In ad ...
From $290 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: "Island Time" is a newly renovated 2-bedroom, 2-bath condo in the gated La Brisa community. Located across fro ...
From $314 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Captain's Wheel at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home feat ...
From $342 per night (USD)
VRBO
From $617 per night (USD)
Expedia
**WALKING ON SUNSHINE** Ocean Condo & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! WALKING ON SU ...
From $617 per night (USD)
Expedia
From $314 per night (USD)
VRBO
A Low Tide at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award winning gated community of the T ...
From $314 per night (USD)
VRBO
From $1743 per night (USD)
Expedia
Southern Palms - Steps to Duval with Private Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, o ...
From $1743 per night (USD)
Expedia
From $433 per night (USD)
VRBO
PELICAN'S PERCH Summer Rates!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town neighborhood ...
From $433 per night (USD)
VRBO
From $484 per night (USD)
Expedia
A Sunset & Harbour View at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, ...
From $484 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $350 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Carriage House at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $302 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Unique Home with loft @ Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $301 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Marlin Blue at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $257 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Cool Breeze @ the Key West Golf Club in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club- This community is located on Stock Island which is five miles from Duval Street a ...
From $367 per night (USD)
VRBO
From $206 per night (USD)
Expedia
Tropical Breezes at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $206 per night (USD)
Expedia
From $211 per night (USD)
VRBO
ISLAND TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $211 per night (USD)
VRBO
From $1086 per night (USD)
Expedia
3-Story spacious conch style home w/ private pool & dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1086 per night (USD)
Expedia
From $797 per night (USD)
VRBO
**LAYOVER in PARADISE** New Home / Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! A home design ...
From $797 per night (USD)
VRBO
From $294 per night (USD)
Expedia
1 Island Time Escape at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1 ISLAND TIME ESCAPE at the Truman Annex This Foundry townhome is a Bostonian style 3 level home located in Old Town K ...
From $294 per night (USD)
Expedia
From $290 per night (USD)
VRBO
A License to Chill at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The historic Foundry, known as building #101, features three story townhomes, located in the award-winning residential n ...
From $290 per night (USD)
VRBO
From $886 per night (USD)
Expedia
DOLPHIN WATCH at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attrac ...
From $886 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Amberjack at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $336 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Catch of the Day at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Tr ...
From $1000 per night (USD)
Expedia
From $205 per night (USD)
VRBO
SOUTHARD COMFORT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beau ...
From $205 per night (USD)
VRBO
From $754 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $754 per night (USD)
Expedia
From $446 per night (USD)
VRBO
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Villa + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! DOCKSIDE DAYD ...
From $446 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Atlantic Escape Luxury Oceanview Key West Condo resort style amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Paradise Escape | Luxury Oceanfront Condo in Key West Monthly Rental | Unit MC322 | 2BR, 2BA | Direct Ocean Vi ...
From $265 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Paradise on the Ocean at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This waterfront two bedroom condo is located in the Truman Annex, Key West's premier residential community. Enjoy endles ...
From $482 per night (USD)
VRBO
From $402 per night (USD)
Expedia
A SUNRISE COTTAGE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...
From $402 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals beyond ...
From $394 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Almost Paradise at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $220 per night (USD)
Expedia
From $2598 per night (USD)
VRBO
Private Heated Pool & Near Duval - The Curry House
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. Best of all, when you ...
From $2598 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Curry House Room 1 - Near Duval, Pool & Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guest ...
From $351 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Private Parking, Heated Pool - Sweet Caroline
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $613 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Private Parking , Heated Pool - Key Lime Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $338 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Heated Pool, Epic Location - Sugar Pie Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $338 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Heated Pool, Epic Location - Honeybun Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $348 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Private Parking, Heated Pool - Banana Split
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $395 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Private Parking, Heated Pool - Creme Brulee Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the hi ...
From $333 per night (USD)
Expedia
From $729 per night (USD)
VRBO
Sunnyside Up - Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Summary: Sunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s "Old Town." With an o ...
From $729 per night (USD)
VRBO
From $270 per night (USD)
Expedia
COLORFUL COCKTAIL @ Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your perfect Key West getaway! Nestled in the coveted Shipyard community of Truman Annex, this beautifully ma ...
From $270 per night (USD)
Expedia
From $377 per night (USD)
VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa + Last Key White Glove Service
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! When explorin ...
From $377 per night (USD)
VRBO
From $357 per night (USD)
Expedia
A Palm Oasis at Mills Place in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming two bedroom, two and one half bath townhome has recently been updated and added to our rental program! Fre ...
From $357 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Coastal Inspired Cottage in Bahama Village Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...
From $274 per night (USD)
VRBO
From $334 per night (USD)
Expedia
MONTHLY RENTAL, 1 block to Duval, POOL, personal resort, 3/3, pets OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...
From $334 per night (USD)
Expedia
From $367 per night (USD)
VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $367 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Island Time On the Green at Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Time on the Green - This is a beautiful, intimate two-story open plan townhome backing to one of two community po ...
From $359 per night (USD)
Expedia
From $431 per night (USD)
VRBO
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block t ...
From $431 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Smith Families Southernmost 2 Bedroom retreat, Key West style beach vacation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $171 per night (USD)
Expedia

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