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Key West Rentals
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- From $362 per night (USD)
VRBO
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 $362 per night (USD)VRBO
- From $402 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 $402 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 $394 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 $394 per night (USD)Expedia
- From $394 per night (USD)
VRBO
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 $394 per night (USD)VRBO
- From $236 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 $236 per night (USD)Expedia
- From $336 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
- 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 $336 per night (USD)VRBO
- From $321 per night (USD)
Expedia
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 $321 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $613 per night (USD)
Expedia
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)Expedia
- From $394 per night (USD)
VRBO
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 $394 per night (USD)VRBO
- From $1291 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 $1291 per night (USD)Expedia
- From $292 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 $292 per night (USD)VRBO
- From $477 per night (USD)
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, ...
From $477 per night (USD)Expedia
- From $568 per night (USD)
VRBO
ABSOLUTE KEY WEST in Truman Annex
- 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 $568 per night (USD)VRBO
- From $713 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 $713 per night (USD)Expedia
- From $519 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
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $519 per night (USD)VRBO
- From $750 per night (USD)
Expedia
Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $750 per night (USD)Expedia
- From $738 per night (USD)
VRBO
Mesa House, Dos by Brightwild | Unreal Location
- 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 Mes ...
From $738 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $710 per night (USD)
VRBO
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $710 per night (USD)VRBO
- From $552 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $552 per night (USD)Expedia
- From $340 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 $340 per night (USD)VRBO
- From $424 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 $424 per night (USD)Expedia
- From $448 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 $448 per night (USD)VRBO
- From $401 per night (USD)
Expedia
GREEN BAMBOO at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Paradise! This 2 bedroom townhouse, one bedroom is a king and the second bedroom features twin beds which can ...
From $401 per night (USD)Expedia
- From $585 per night (USD)
VRBO
Island Time | Gorgeous Condo, Steps To The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: "Island Time" is a newly renovated, 2 bed 2 bath condo located in the gated La Brisa Condominium complex. Situa ...
From $585 per night (USD)VRBO
- From $480 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 $480 per night (USD)Expedia
- From $751 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 $751 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 PricingVRBO
- From $348 per night (USD)
VRBO
Dream Vacation! Near The Famous Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $348 per night (USD)VRBO
- Click For Pricing
VRBO
Amazing Vacation for 16 Guests! 3 Pools, Onsite Dining Pets Allowed!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $2777 per night (USD)
Expedia
Southern Palms by Brightwild | Pool & Parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Southern Palms is the perfect vacation rental for your large group! It is a property split into three separated ...
From $2777 per night (USD)Expedia
- From $482 per night (USD)
VRBO
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 $482 per night (USD)VRBO
- From $724 per night (USD)
Expedia
A SUNSET AND A 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 $724 per night (USD)Expedia
- From $446 per night (USD)
VRBO
ANNIE'S HIDEAWAY at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...
From $446 per night (USD)VRBO
- From $573 per night (USD)
Expedia
Balmy Ocean Breezes Island Sunrises Afternoon Poolside Fun & Key West charm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bluegrass Seabbatical is a Spectacular 3 bedroom 2 bath oceanfront condominium at 1800 Atlantic. Enjoy the incredible oc ...
From $573 per night (USD)Expedia
- From $325 per night (USD)
VRBO
**VILLA MODERNA @ MIDTOWN** Immaculate Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This beautifu ...
From $325 per night (USD)VRBO
- From $641 per night (USD)
Expedia
Exquisite Elegance in Old Town Key West: Your Stylish Sanctuary Awaits
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This stylish Conch home is tucked away on a quiet lane in Old Town Key West. Newly remodeled, impressively decorated 3 B ...
From $641 per night (USD)Expedia
- From $1749 per night (USD)
VRBO
Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!
- Bedrooms:
- 4
- 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 $1749 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Sunsplashed Tropical Gem! Two Amazing Rooms with Breathtaking Views in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $600 per night (USD)VRBO
- From $764 per night (USD)
VRBO
Your Next Getaway is Here! Three Premium Ocean View (w\/ 2 Queens Each), Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $764 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Escape To Paradise in Key West! 2 Relaxing Spaces, Minutes Away From The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $425 per night (USD)VRBO
- From $1018 per night (USD)
VRBO
Close to Nearest Beach! Four Premium Ocean View Rooms (w\/ 2 Queen Beds), Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1018 per night (USD)VRBO
- From $494 per night (USD)
VRBO
Amazing Stay in the Keywest! Two Deluxe Pool View Two Queen Beds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $494 per night (USD)VRBO
- From $1199 per night (USD)
VRBO
Perfect Staycation! Four Fantastic Ocean View Rooms, Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1199 per night (USD)VRBO
- From $658 per night (USD)
VRBO
Delight In The Florida Sun! 3 Gorgeous Spaces In Sun Soaked Key West, Onsite Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $658 per night (USD)VRBO
- From $779 per night (USD)
VRBO
3x Deluxe Pool View Two Queen Beds at 24 North Hotel Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $779 per night (USD)VRBO
- From $510 per night (USD)
VRBO
Your Next Beach Getaway is Here! Two Premium Ocean View Rooms, Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $510 per night (USD)VRBO
- From $1038 per night (USD)
VRBO
Close to the Nearest Beach! Four Amazing Rooms w\/ Pool View
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1038 per night (USD)VRBO
- From $665 per night (USD)
VRBO
Perfect Beach Getaway! 3 Amazing Rooms Rooms, Driving Distance to the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $665 per night (USD)VRBO
- From $591 per night (USD)
VRBO
Key West Vacation! 3 Comfortable Units, Onsite Pool, Close to Smathers Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $591 per night (USD)VRBO
- From $667 per night (USD)
VRBO
Amazing Stay Perfect for the Whole Family! Four Convenient Rooms, Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $667 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Two Amazing Rooms (w\/ 2 Queen Beds), Outdoor Pool, Close to Nearest Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $399 per night (USD)VRBO
- From $891 per night (USD)
VRBO
You Found it! Amazing Stay w\/ 4 Deluxe Pool View (w\/ Two Queen Beds Each)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $891 per night (USD)VRBO
- From $253 per night (USD)
VRBO
Amazing Stay in the Key West! Premium Ocean View w\/ King Bed, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $253 per night (USD)VRBO
- From $154 per night (USD)
VRBO
Perfect Location for Your Next Getaway! Amazing Room w\/ King Bed, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $154 per night (USD)VRBO
- From $268 per night (USD)
VRBO
Dream Vacation! Fantastic Panoramic Ocean View Room, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $268 per night (USD)VRBO
- From $223 per night (USD)
VRBO
Short Drive to the Nearest Beach! Amazing Deluxe Room w\/ Amazing Pool View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $223 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Fantastic Beach Vacation! Amazing Room, 2 Queen Beds, Pool w\/ Sun Loungers
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $261 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Rare Find! 2 Comfortable Rooms In The Heart Of Key West Minutes From The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $395 per night (USD)VRBO
- From $232 per night (USD)
VRBO
Look No More! Perfect for a Getaway! Close to Nearest Beach, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $232 per night (USD)VRBO
- From $224 per night (USD)
VRBO
Perfect Location! Spacious Deluxe Pool View, Outdoor Swimming Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $224 per night (USD)VRBO
- From $226 per night (USD)
VRBO
Beautiful Key West! Close to the Beach! Amazing Ocean View, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $226 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Escape To Paradise in Key West! Relaxing Room, Minutes Away From The Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $215 per night (USD)VRBO
- From $236 per night (USD)
VRBO
Key West Paradise Getaway! Hidden Key West Gem Minutes From The Beach, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $236 per night (USD)VRBO
- Click For Pricing
Expedia
KEY WEST - Weekly Stay Only - 2 Bedroom 2 Bathrooms Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Coconut Mallory Marina and Resort is located in the southernmost city in the continental United States. Key West, Fl ...
Click For PricingExpedia
- From $325 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 $325 per night (USD)VRBO
- From $463 per night (USD)
Expedia
New home for rent located two blocks away from Duval and the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
NEW LISTING!!! THE PROPERTY: Brand new luxury 3 bedroom home built in 2019 located on a quiet street just 2 blocks off D ...
From $463 per night (USD)Expedia
- From $383 per night (USD)
VRBO
Carriage House at Grand Maloney by Brightwild
- 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 br ...
From $383 per night (USD)VRBO
- From $336 per night (USD)
Expedia
Bunk Room at the Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $336 per night (USD)Expedia
- From $273 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 $273 per night (USD)VRBO
- From $253 per night (USD)
Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $253 per night (USD)Expedia
- From $445 per night (USD)
VRBO
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 $445 per night (USD)VRBO
- From $357 per night (USD)
Expedia
COOL BREEZE @ the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...
From $357 per night (USD)Expedia
- From $381 per night (USD)
VRBO
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 $381 per night (USD)VRBO
- From $417 per night (USD)
Expedia
MANATEE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $417 per night (USD)Expedia
- From $381 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 $381 per night (USD)VRBO
- From $632 per night (USD)
Expedia
Classic Key West condo w\/ private parking, covered porches, & shared pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $632 per night (USD)Expedia
- From $401 per night (USD)
VRBO
**LAYOVER in PARADISE @ CASA MARINA** New Home \/ Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A home design ...
From $401 per night (USD)VRBO
- From $620 per night (USD)
Expedia
AAH PARADISE at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
AAH PARADISE This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been r ...
From $620 per night (USD)Expedia
- From $460 per night (USD)
VRBO
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
When choosing your dates, please keep in mind that we rent a minimum of 7 DAYS from SATURDAY to SATURDAY. (One exception ...
From $460 per night (USD)VRBO
- From $633 per night (USD)
Expedia
A LICENSE TO CHILL at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...
From $633 per night (USD)Expedia
- From $1309 per night (USD)
VRBO
**BAHAMIAN BLUES @ BAHAMA VILLAGE** Impeccable Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BAHAMIAN BLUE ...
From $1309 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Quaint Island Escape Condo w\/Spacious Balcony Deck in Beautiful Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental ...
From $236 per night (USD)Expedia
- From $1261 per night (USD)
VRBO
DOLPHIN WATCH in Key West @ The Truman Annex Compass Realty
- 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 $1261 per night (USD)VRBO
- From $477 per night (USD)
Expedia
AMBERJACK at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $477 per night (USD)Expedia
- From $998 per night (USD)
VRBO
CATCH OF THE DAY at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $998 per night (USD)VRBO
- From $456 per night (USD)
Expedia
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 $456 per night (USD)Expedia
- From $139 per night (USD)
VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $139 per night (USD)VRBO
- From $850 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 $850 per night (USD)Expedia
- From $567 per night (USD)
VRBO
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + 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! DOCKSIDE DAYD ...
From $567 per night (USD)VRBO
- From $761 per night (USD)
Expedia
Sunnyside Up by Brightwild | Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This charming Key West conch home is situated on United Street, on the edge of "Old Town" Key West. The kitchen ...
From $761 per night (USD)Expedia
- From $197 per night (USD)
VRBO
South Beachside at 1800 Atlantic by Smathers Beach & 10 minute bike Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully renovated 2 bedroom 2 bath ocean view Condo at 1800 Atlantic. Fabulous layout where both bedrooms and the li ...
From $197 per night (USD)VRBO
- From $345 per night (USD)
VRBO
Lovely 2 bedroom, 2 bathroom steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Key West at La Brisa, a gated Condo community, just steps from the beach on Key West's Atlantic coast. Walk in ...
From $345 per night (USD)VRBO
- From $736 per night (USD)
VRBO
PARADISE ON THE OCEANat The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $736 per night (USD)VRBO
- From $490 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 $490 per night (USD)Expedia
- From $444 per night (USD)
VRBO
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Cocktails & Dreams," an impeccably updated second-floor condo located in the coveted Shipyard Condominiums. ...
From $444 per night (USD)VRBO
- From $410 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 $410 per night (USD)Expedia