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From $329 per night (USD)
VRBO
**BIRD of PARADISE** Elegant Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Like witnessi ...
From $329 per night (USD)
VRBO
From $2754 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 $2754 per night (USD)
Expedia
From $3049 per night (USD)
VRBO
Bananas Foster, Downtown | Epic Guesthouse!
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 $3049 per night (USD)
VRBO
From $681 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 $681 per night (USD)
Expedia
From $324 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 $324 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $276 per night (USD)
Expedia
From $1314 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1314 per night (USD)
VRBO
From $444 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $444 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $525 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $461 per night (USD)
VRBO
From $229 per night (USD)
VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & 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! This freshly ...
From $229 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
Poolside Paradise | Private Oasis, 1 Block to Duval!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1168 per night (USD)
Expedia
$Poolside Retreat | Cottage w\/ Pool$
From $374 per night (USD)
VRBO
Poolside Retreat | Cottage w\/ Pool
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 $374 per night (USD)
VRBO
From $390 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 $390 per night (USD)
Expedia
From $1531 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 $1531 per night (USD)
VRBO
From $432 per night (USD)
Expedia
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 $432 per night (USD)
Expedia
From $518 per night (USD)
VRBO
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 $518 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Hip Studio in Old Town - Walk to the Beach!
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 $399 per night (USD)
Expedia
From $413 per night (USD)
VRBO
'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 $413 per night (USD)
VRBO
From $437 per night (USD)
Expedia
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 $437 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Galleon Resort available Jan 4-18 2025
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You can book 1 or both weeks. Saturday-Saturday. This unit has a queen size bed. Updated ceramic stand up shower. The un ...
From $362 per night (USD)
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 $1165 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 $1165 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 $543 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 $543 per night (USD)
VRBO
From $576 per night (USD)
Expedia
Sea Breeze, Near Downtown!| Off-Street Parking!
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 $576 per night (USD)
Expedia
From $1343 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 $1343 per night (USD)
VRBO
From $702 per night (USD)
Expedia
Panoramic Ocean: Beach from every window
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Paradise Found hes been renovated for 2020 and beyond. New Master Bathroom, Reconfigured Master Bedroom and Re ...
From $702 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 $845 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 $845 per night (USD)
Expedia
From $1129 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 $1129 per night (USD)
VRBO
From $674 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 $674 per night (USD)
Expedia
From $1072 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 $1072 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
$Coconut Palm, Great Location | Island Home w\/ Pool$
From $1080 per night (USD)
VRBO
Coconut Palm, Great Location | Island Home w\/ Pool
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 $1080 per night (USD)
VRBO
From $1039 per night (USD)
Expedia
Casa Key West | Pool & Free Parking
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 $1039 per night (USD)
Expedia
From $384 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 $384 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 ...
Click For Pricing
Expedia
From $396 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 $396 per night (USD)
VRBO
From $472 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 $472 per night (USD)
Expedia
From $433 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 $433 per night (USD)
VRBO
From $354 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 $354 per night (USD)
Expedia
$Salt Pond Hideaway | Cute Condo w\/ Pool, Hot Tub$
From $240 per night (USD)
VRBO
Salt Pond Hideaway | Cute Condo w\/ Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: - Recently updated this spacious, airy rental is the perfect location for your next Key West getaway! - If you ...
From $240 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
$Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View$
Click For Pricing
VRBO
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
VRBO
From $489 per night (USD)
Expedia
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 $489 per night (USD)
Expedia
From $473 per night (USD)
VRBO
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 $473 per night (USD)
VRBO
From $292 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $4559 per night (USD)
VRBO
**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 $4559 per night (USD)
VRBO
From $676 per night (USD)
Expedia
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 $676 per night (USD)
Expedia
From $492 per night (USD)
VRBO
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 $492 per night (USD)
VRBO
From $1502 per night (USD)
Expedia
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 $1502 per night (USD)
Expedia
From $450 per night (USD)
VRBO
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 $450 per night (USD)
VRBO
From $588 per night (USD)
Expedia
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 $588 per night (USD)
Expedia
From $279 per night (USD)
VRBO
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 $279 per night (USD)
VRBO
From $508 per night (USD)
Expedia
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 $508 per night (USD)
Expedia
From $392 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 $392 per night (USD)
VRBO
From $448 per night (USD)
Expedia
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 $448 per night (USD)
Expedia
$*Casa-Amelia-Key-West* 1\/2 block off Duval Street$
From $587 per night (USD)
VRBO
*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)
VRBO
$Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony$
From $654 per night (USD)
Expedia
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 $654 per night (USD)
Expedia
From $209 per night (USD)
VRBO
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 $209 per night (USD)
VRBO
From $1328 per night (USD)
Expedia
Commodore's Cove | Epic Location!
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 $1328 per night (USD)
Expedia
From $2738 per night (USD)
VRBO
Commodore's Compound| HUGE Home!
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 $2738 per night (USD)
VRBO
From $1458 per night (USD)
Expedia
Seaport Suite | 2nd Story Hideaway!
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 $1458 per night (USD)
Expedia
From $486 per night (USD)
VRBO
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 $486 per night (USD)
VRBO
From $995 per night (USD)
Expedia
Conch Cove | Heated Pool & Prime Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Conch Cove is a true Key West oasis! Nestled away off of Simonton St, this 3 bed 3 bath home sits just 1 short ...
From $995 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 $3492 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 $3492 per night (USD)
Expedia
From $448 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 $448 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 $690 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 $690 per night (USD)
VRBO
From $425 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 $425 per night (USD)
Expedia
From $431 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 $431 per night (USD)
VRBO
From $464 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 $464 per night (USD)
Expedia
From $728 per night (USD)
VRBO
**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 30 days prior to your arrival! Spanning an e ...
From $728 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Peachy Keen: October, November, December Specials!
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 $342 per night (USD)
Expedia
From $848 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 $848 per night (USD)
VRBO
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $442 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 $442 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 $544 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 $544 per night (USD)
Expedia
From $431 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 $431 per night (USD)
VRBO
From $369 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 $369 per night (USD)
Expedia
From $467 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 $467 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 $613 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 $613 per night (USD)
VRBO
From $299 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 $299 per night (USD)
Expedia
From $1477 per night (USD)
VRBO
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 $1477 per night (USD)
VRBO
From $432 per night (USD)
Expedia
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 $432 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $577 per night (USD)
Expedia
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 $577 per night (USD)
Expedia
From $720 per night (USD)
VRBO
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 $720 per night (USD)
VRBO
$Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking$
From $752 per night (USD)
Expedia
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 $752 per night (USD)
Expedia
$Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking$
From $734 per night (USD)
VRBO
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 $734 per night (USD)
VRBO
From $655 per night (USD)
Expedia
Mesa House, Dos | Unreal Location
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 $655 per night (USD)
Expedia
Click For Pricing
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 $1008 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 $1008 per night (USD)
Expedia
$Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking$
From $837 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 $837 per night (USD)
VRBO
From $215 per night (USD)
Expedia
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 $215 per night (USD)
Expedia
From $409 per night (USD)
VRBO
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 $409 per night (USD)
VRBO
From $425 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 $425 per night (USD)
Expedia

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