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From $487 per night (USD)
VRBO
Pet Friendly, & Near Duval - Poolside Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $487 per night (USD)
VRBO
From $633 per night (USD)
Expedia
Updated home with private pool, patio, & grill in enclosed tropical backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $633 per night (USD)
Expedia
From $3452 per night (USD)
VRBO
Balcony, & Pool, Near Duval - Bananas Foster
Bedrooms:
8
Bathrooms:
9
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3452 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $613 per night (USD)
Expedia
From $584 per night (USD)
VRBO
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $584 per night (USD)
VRBO
From $1699 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1699 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $513 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. 3 bedro ...
From $532 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $545 per night (USD)
VRBO
From $537 per night (USD)
Expedia
'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic ...
From $537 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $560 per night (USD)
VRBO
From $1932 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1932 per night (USD)
Expedia
Click For Pricing
VRBO
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
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VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
Expedia
From $1550 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1550 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
Expedia
From $528 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $528 per night (USD)
VRBO
From $1441 per night (USD)
Expedia
Steps from Duval with Private Pool – Coconut Palm
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Coconut Palm is the perfect place for your beautiful tropical getaway in Key West. It is located just one block ...
From $1441 per night (USD)
Expedia
From $1310 per night (USD)
VRBO
Parking & Shared Pool - Casa Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: - Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with p ...
From $1310 per night (USD)
VRBO
From $831 per night (USD)
Expedia
Private Parking & Near Downtown - Sea Breeze
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $831 per night (USD)
Expedia
From $1355 per night (USD)
VRBO
Coastal Comfort; Waterfront Luxury Home with private pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1355 per night (USD)
VRBO
From $795 per night (USD)
Expedia
Panoramic Ocean: Beach from every window
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Paradise Found is perched on the top floor with breathtaking Ocean Views, Reconfigured Master Bedroom and Rem ...
From $795 per night (USD)
Expedia
$Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!$
From $339 per night (USD)
VRBO
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 $339 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Penthouse Beach Ocean Views- Live the Dream
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You feel the excitement the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm ...
From $783 per night (USD)
Expedia
From $1343 per night (USD)
VRBO
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
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 $1343 per night (USD)
VRBO
From $813 per night (USD)
Expedia
Beach Penthouse: Ocean Views from every room Tropical Excellence
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean views from every room with floor to ceiling windows. Feel the warm tropical breezes as the palm trees sway to the ...
From $813 per night (USD)
Expedia
From $1383 per night (USD)
VRBO
Banana Breeze: Oceanview 4-bedroom 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 $1383 per night (USD)
VRBO
From $755 per night (USD)
Expedia
Hemingway Hideaway in the Truman Annex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $755 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Fantasy Fest Special Discount-Beach House Ocean View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
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 $360 per night (USD)
VRBO
Click For Pricing
Expedia
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
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Expedia
From $1484 per night (USD)
VRBO
A SUNSET BREEZE Beautiful private home with pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $1484 per night (USD)
VRBO
From $431 per night (USD)
Expedia
A SUNSET POOLSIDE in the Truman Annex
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 $431 per night (USD)
Expedia
From $466 per night (USD)
VRBO
ARCHIPELAGO ll at The Truman Annex in Key West
Bedrooms:
3
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 $466 per night (USD)
VRBO
From $333 per night (USD)
Expedia
ALHAMBRA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $333 per night (USD)
Expedia
From $608 per night (USD)
VRBO
SAILOR'S STORY at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $608 per night (USD)
VRBO
From $440 per night (USD)
Expedia
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 $440 per night (USD)
Expedia
From $442 per night (USD)
VRBO
CONCH ISLAND 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 $442 per night (USD)
VRBO
$*Casa-Amelia-Key-West* 1\/2 block off Duval Street$
From $587 per night (USD)
Expedia
*Casa-Amelia-Key-West* 1\/2 block off Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $587 per night (USD)
Expedia
$Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony$
From $1537 per night (USD)
VRBO
Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $1537 per night (USD)
VRBO
From $210 per night (USD)
Expedia
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $210 per night (USD)
Expedia
From $1289 per night (USD)
VRBO
Parking, & Near Duval - Commodore's Cove
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $1289 per night (USD)
VRBO
From $2948 per night (USD)
Expedia
Hot Tub, & Near Duval - Commodore's Compound
Bedrooms:
7
Bathrooms:
10
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2948 per night (USD)
Expedia
From $1310 per night (USD)
VRBO
Hot Tub, & Near Duval - Seaport Suite
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Situated in the heart of Old Town Key West, Seaport Suite is the perfect vacation spot for large groups of up t ...
From $1310 per night (USD)
VRBO
From $496 per night (USD)
Expedia
SEASCAPE 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 $496 per night (USD)
Expedia
From $421 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 $421 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Conch House in the Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $387 per night (USD)
Expedia
Click For Pricing
VRBO
ISLAND SPA in the Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
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VRBO
$Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View$
Click For Pricing
Expedia
Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For Pricing
Expedia
From $410 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 $410 per night (USD)
VRBO
From $399 per night (USD)
Expedia
A Bella Capri in Key West by the Beach! *Monthly rental*
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $399 per night (USD)
Expedia
From $421 per night (USD)
VRBO
OYSTER'S PEARL at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $421 per night (USD)
VRBO
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $3494 per night (USD)
Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..
Bedrooms:
8
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $3494 per night (USD)
Expedia
From $718 per night (USD)
VRBO
A LATITUDE ADJUSTMENT at the Truman Annex in Key West
Bedrooms:
3
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 $718 per night (USD)
VRBO
From $501 per night (USD)
Expedia
ANOTHER DAY IN 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 $501 per night (USD)
Expedia
From $392 per night (USD)
VRBO
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 $392 per night (USD)
VRBO
From $432 per night (USD)
Expedia
ANOTHER THREE HOUR TOUR 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 $432 per night (USD)
Expedia
From $416 per night (USD)
VRBO
CONCH RETREAT Truman Annex Condo with 2 decks, Close to Beach, 2 Bikes
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the prestigious Truman An ...
From $416 per night (USD)
VRBO
From $509 per night (USD)
Expedia
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
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 $509 per night (USD)
Expedia
From $605 per night (USD)
VRBO
Private Heated Pool, Cabana, & Prime Key West Location Near Truman Annex!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated po ...
From $605 per night (USD)
VRBO
From $2686 per night (USD)
Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $2686 per night (USD)
Expedia
From $505 per night (USD)
VRBO
ADRIFT in Key West at the Truman Annex
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 $505 per night (USD)
VRBO
From $228 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 $228 per night (USD)
Expedia
From $680 per night (USD)
VRBO
FOREVER YOUNG at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $680 per night (USD)
VRBO
From $449 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 $449 per night (USD)
Expedia
From $456 per night (USD)
VRBO
HAVANA VIEWS 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 $456 per night (USD)
VRBO
From $414 per night (USD)
Expedia
SAND CRAB CABANA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $414 per night (USD)
Expedia
From $795 per night (USD)
VRBO
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
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 $795 per night (USD)
VRBO
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $597 per night (USD)
Expedia
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
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 $597 per night (USD)
Expedia
From $271 per night (USD)
VRBO
The Estela, Old Town Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away just 1 block from the action of Duval Street lies our newest space located at 613 Fleming Street. Find your ...
From $271 per night (USD)
VRBO
From $353 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 $353 per night (USD)
Expedia
From $361 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $361 per night (USD)
VRBO
From $1952 per night (USD)
Expedia
QUEEN EMMA in the Truman Annex 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 $1952 per night (USD)
Expedia
From $400 per night (USD)
VRBO
A PLEASANT STAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $400 per night (USD)
VRBO
Click For Pricing
Expedia
ANGEL FISH at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...
Click For Pricing
Expedia
From $630 per night (USD)
VRBO
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $630 per night (USD)
VRBO
From $821 per night (USD)
Expedia
TROPICAL EXECUTIVE at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $821 per night (USD)
Expedia
$Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking$
From $832 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 must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $832 per night (USD)
VRBO
$Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking$
From $1028 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 must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $1028 per night (USD)
Expedia
From $734 per night (USD)
VRBO
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...
From $734 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned 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 $399 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Steps To The Beach And The Sunrise-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnis ...
From $374 per night (USD)
VRBO
From $254 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 $254 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $803 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in ...
From $310 per night (USD)
Expedia
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VRBO
2 BR at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium ...
Click For Pricing
VRBO
$Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $1133 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 must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $1133 per night (USD)
Expedia
$Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $970 per night (USD)
VRBO
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: All guests must be 25 years of age or older at this property- NO EXCEPTIONS RESTRICTIONS: We do not ...
From $970 per night (USD)
VRBO
From $437 per night (USD)
Expedia
SUN, SEA, AND SKY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sun Sea and Sky is blocks from bustling Duval Street, the heart of Old Town Key West, and an easy walk to restaurants, s ...
From $437 per night (USD)
Expedia
From $236 per night (USD)
VRBO
December Reduced Rate-Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and c ...
From $236 per night (USD)
VRBO
From $434 per night (USD)
Expedia
ANGLER'S RETREAT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...
From $434 per night (USD)
Expedia
From $497 per night (USD)
VRBO
A Seaglass 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 $497 per night (USD)
VRBO
From $562 per night (USD)
Expedia
GREEN BAMBOO at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Paradise! This 2 bedroom townhouse, one bedroom is a king and the second bedroom features twin beds which can ...
From $562 per night (USD)
Expedia
From $874 per night (USD)
VRBO
Balcony, Pet Friendly, & Shared Pool - Island Time
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: "Island Time" is a newly renovated, 2 bed 2 bath condo located in the gated La Brisa Condominium complex. Situa ...
From $874 per night (USD)
VRBO
From $640 per night (USD)
Expedia
CAPTAINS WHEEL at The Truman Annex in Key West
Bedrooms:
3
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 $640 per night (USD)
Expedia
From $1207 per night (USD)
VRBO
**WALKING ON SUNSHINE @ THE BEACH** Ocean Condo & Large Pool + LAST KEY SERVICES
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 $1207 per night (USD)
VRBO
From $425 per night (USD)
Expedia
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 $425 per night (USD)
Expedia
Click For Pricing
VRBO
Private luxury retreat all included.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
All included in this large home has a huge master bedroom with 2 walking closets, opens to large wrap around balcony ove ...
Click For Pricing
VRBO
$Key West Retreat Near Duval Street | Scenic Resort w\/ Outdoor Pool$
From $871 per night (USD)
VRBO
Key West Retreat Near Duval Street | Scenic Resort w\/ Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $871 per night (USD)
VRBO
From $2438 per night (USD)
VRBO
Steps from Duval with Private Pool – Southern Palms
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Summary: Southern Palms is the perfect vacation rental for your large group! It is a property split into three separated ...
From $2438 per night (USD)
VRBO
From $642 per night (USD)
Expedia
PELICAN'S PERCH at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $642 per night (USD)
Expedia

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