Key West Rentals
From $394 per night (USD)VRBO
Paradise Island Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island C ...
From $394 per night (USD)VRBO
From $511 per night (USD)Expedia
Bimini Suite one block of Famous Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island C ...
From $511 per night (USD)Expedia
From $532 per night (USD)VRBO
Mesa House Dos- Updated Home In Perfect Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Whether you're lounging on the front porch's rocking chair or enjoying a seafood dinner inside, this 2 bedroom ...
From $532 per night (USD)VRBO
From $595 per night (USD)VRBO
3 bedroom accommodation in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Portside Villa, a multi-million dollar old town treasure Vacation Townhouse for rent by the month Welcome to the m ...
From $595 per night (USD)VRBO
From $264 per night (USD)VRBO
SUN, SEA, AND SKY in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to rest ...
From $264 per night (USD)VRBO
From $336 per night (USD)VRBO
ANGLER'S RETREAT @ the Truman Annex
- 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 $336 per night (USD)VRBO
From $280 per night (USD)VRBO
Downtown Location in Historic District-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 $280 per night (USD)VRBO
From $290 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 $290 per night (USD)Expedia
From $156 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 $156 per night (USD)VRBO
From $545 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 $545 per night (USD)Expedia
From $234 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 $234 per night (USD)VRBO
From $313 per night (USD)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 ...
From $313 per night (USD)Expedia
From $452 per night (USD)VRBO
Grand Bahama Suite one block of Famous Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island C ...
From $452 per night (USD)VRBO
From $470 per night (USD)Expedia
Nassau Suite one block of Famous Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island C ...
From $470 per night (USD)Expedia
From $130 per night (USD)VRBO
**MARINA MELODIES @ SUNSET MARINA** Waterfront 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! Imagine relax ...
From $130 per night (USD)VRBO
From $565 per night (USD)Expedia
Island Time - Modern Condo, Steps To The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: NEWLY RENOVATED! Island Time is a bright and airy two bedroom condo located at the gated La Brisa Condominium c ...
From $565 per night (USD)Expedia
From $379 per night (USD)VRBO
CAPTAINS WHEEL in the Truman Annex
- 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 $379 per night (USD)VRBO
From $710 per night (USD)Expedia
**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 $710 per night (USD)Expedia
From $336 per night (USD)VRBO
A LOW TIDE in Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Tr ...
From $336 per night (USD)VRBO
From $1000 per night (USD)Expedia
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 ...
From $1000 per night (USD)Expedia
From $336 per night (USD)VRBO
HEMINGWAY'S HAMMOCK in the Truman Annex
- 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 $336 per night (USD)VRBO
From $307 per night (USD)VRBO
GREEN BAMBOO in the Truman Annex
- 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 $307 per night (USD)VRBO
From $555 per night (USD)VRBO
Superb Location! Pet-friendly, 3 Pools, Near Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $555 per night (USD)VRBO
From $547 per night (USD)VRBO
Dream Vacation! Near 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 $547 per night (USD)VRBO
From $1162 per night (USD)VRBO
Ultimate Vacation! Harbor View, 3 Pools, Pets Allowed!
- 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 $1162 per night (USD)VRBO
From $5511 per night (USD)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 ...
From $5511 per night (USD)VRBO
From $1339 per night (USD)VRBO
Look No More! Onsite Dining, Bicycle Rental, Pets Allowed, 3 Swimming Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1339 per night (USD)VRBO
From $2374 per night (USD)Expedia
Southern Palms- NEW Pool, Lanai, Hot Tub & 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 $2374 per night (USD)Expedia
From $336 per night (USD)VRBO
FLAMINGO BEACH in the Truman Annex
- 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 $336 per night (USD)VRBO
From $379 per night (USD)VRBO
PELICAN'S PERCH in the Truman Annex
- 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 $379 per night (USD)VRBO
From $586 per night (USD)VRBO
A SUNSET AND A HARBOUR VIEW in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, ...
From $586 per night (USD)VRBO
From $350 per night (USD)VRBO
ANNIE'S HIDEAWAY in the Truman Annex
- 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 $350 per night (USD)VRBO
From $350 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 $350 per night (USD)VRBO
From $360 per night (USD)Expedia
Walk to Higgs Beach Hideaway- Heated Amazing Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Looking for something close enough to everything, but far enough away to feel like your own private island sanc ...
From $360 per night (USD)Expedia
From $1443 per night (USD)VRBO
Beach Getaway! 3 Convenient Units, 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 $1443 per night (USD)VRBO
From $916 per night (USD)VRBO
Sunsplashed Tropical Gem! 2 Great Units 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 $916 per night (USD)VRBO
From $1424 per night (USD)VRBO
3x Premium Ocean View 2 Queens 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 $1424 per night (USD)VRBO
From $759 per night (USD)VRBO
Escape To Paradise in Key West! 2 Relaxing Units, 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 $759 per night (USD)VRBO
From $1899 per night (USD)VRBO
4x Premium Ocean View 2 Queens at 24 North Hotel Key West
- 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 $1899 per night (USD)VRBO
From $850 per night (USD)VRBO
2x Deluxe Pool View Two Queen Beds at 24 North Hotel 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 $850 per night (USD)VRBO
From $1552 per night (USD)VRBO
4x Standard 2 Queens at 24 North Hotel Key West
- 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 $1552 per night (USD)VRBO
From $1835 per night (USD)VRBO
Perfect staycation! 4 Great Units, Onsite Pool, Close to Smathers Beach!
- 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 $1835 per night (USD)VRBO
From $1103 per night (USD)VRBO
Delight In The Florida Sun! 3 Classy 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 $1103 per night (USD)VRBO
From $1274 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 $1274 per night (USD)VRBO
From $175 per night (USD)VRBO
Namasta on the Beach Key West Available February 2023- Call now to book
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Namasta by the beach is a Beautifully decorated and renovated 2 bedroom 2 bath Island view Condominium. This unit also ...
From $175 per night (USD)VRBO
From $950 per night (USD)VRBO
2x Premium Ocean View 2 Queens at 24 North Hotel 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 $950 per night (USD)VRBO
From $1646 per night (USD)VRBO
Close to the Beach! 4 Great Units, Short Drive to Key West Harbour!
- 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 $1646 per night (USD)VRBO
From $1138 per night (USD)VRBO
Perfect Beach Getaway! 3 Comfortable Units, 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 $1138 per night (USD)VRBO
From $1238 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 $1238 per night (USD)VRBO
From $1515 per night (USD)VRBO
Fun For the Whole Family! 4 Convenient Units, an Onsite 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 $1515 per night (USD)VRBO
From $776 per night (USD)VRBO
2x Standard 2 Queens at 24 North Hotel 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 $776 per night (USD)VRBO
From $1694 per night (USD)VRBO
4x Deluxe Pool View Two Queen Beds at 24 North Hotel Key West
- 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 $1694 per night (USD)VRBO
From $521 per night (USD)VRBO
Premium King Ocean View at 24 North Hotel Key West
- 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 $521 per night (USD)VRBO
From $358 per night (USD)VRBO
Bask In The Key West Sun! Stay Minutes Away From Old Town & Duval Street!
- 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 $358 per night (USD)VRBO
From $475 per night (USD)VRBO
Dream Vacation! Pool, Near the Beach, On-site 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 $475 per night (USD)VRBO
From $414 per night (USD)VRBO
Less Than 5 Miles to Beach! Minutes away from County Beach, Onsite 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 $414 per night (USD)VRBO
From $435 per night (USD)VRBO
Fantastic Beach Vacation! Near County Beach, Onsite 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 $435 per night (USD)VRBO
From $377 per night (USD)VRBO
Standard King at 24 North Hotel Key West
- 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 $377 per night (USD)VRBO
From $826 per night (USD)VRBO
Rare Find! 2 Comfortable Units 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 $826 per night (USD)VRBO
From $483 per night (USD)VRBO
Look No More! Perfect for a Getaway, Close to Smathers Beach, Onsite 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 $483 per night (USD)VRBO
From $448 per night (USD)VRBO
Deluxe Pool View King at 24 North Hotel Key West
- 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 $448 per night (USD)VRBO
From $490 per night (USD)VRBO
Beautiful Key West! Minutes Away from the Beach! Close to Key West Harbour
- 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 $490 per night (USD)VRBO
From $380 per night (USD)VRBO
Standard 2 Queens at 24 North Hotel Key West
- 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 $380 per night (USD)VRBO
From $432 per night (USD)VRBO
Key West Paradise Getaway! Hidden Key West Gem Minutes From The Beach
- 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 $432 per night (USD)VRBO
From $161 per night (USD)VRBO
Old Town Key West Hidden Cottage on Whitehead
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is small ...
From $161 per night (USD)VRBO
From $1474 per night (USD)Expedia
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 $1474 per night (USD)Expedia
From $808 per night (USD)VRBO
Paradise on a Quiet Lane
- 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 $808 per night (USD)VRBO
From $299 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 $299 per night (USD)Expedia
From $315 per night (USD)VRBO
Carriage House at Grand Maloney with Parking
- 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 $315 per night (USD)VRBO
From $320 per night (USD)Expedia
Bunk Room at Grand Maloney Hotel with Pool!
- 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 $320 per night (USD)Expedia
From $320 per night (USD)VRBO
2 Blocks east of Sloppy Joes on QUIET Peacon Lane. Kids and Pets welcome.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Single family home. Not a condo. We welcome kids, pets, partners, friends. Free parking for 2-3 vehicles. PRIVATE heat ...
From $320 per night (USD)VRBO
From $197 per night (USD)Expedia
Old Town Key West classic w/ private heated pool and enclosed patio area
- 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 $197 per night (USD)Expedia
From $301 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 $301 per night (USD)VRBO
From $586 per night (USD)VRBO
AAH PARADISE in the Truman Annex
- 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 $586 per night (USD)VRBO
From $370 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 $370 per night (USD)VRBO
From $586 per night (USD)VRBO
A LICENSE TO CHILL in the Truman Annex
- 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 $586 per night (USD)VRBO
From $385 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 $385 per night (USD)VRBO
From $325 per night (USD)Expedia
PELICAN - A cheerful condo in beautiful Truman Annex and close to Duval St.
- Bedrooms:
- 1
- 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 $325 per night (USD)Expedia
From $307 per night (USD)VRBO
STARSHINE KEY WEST in the Truman Annex
- 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 $307 per night (USD)VRBO
From $357 per night (USD)VRBO
MARLIN BLUE in the Truman Annex
- 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 $357 per night (USD)VRBO
From $250 per night (USD)VRBO
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 $250 per night (USD)VRBO
From $331 per night (USD)VRBO
TROPICAL BREEZES in the Truman Annex
- 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 $331 per night (USD)VRBO
From $350 per night (USD)VRBO
MANATEE in the Truman Annex
- 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 $350 per night (USD)VRBO
From $307 per night (USD)VRBO
ISLAND TIME in the Truman Annex
- 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 $307 per night (USD)VRBO
From $341 per night (USD)VRBO
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 $341 per night (USD)VRBO
From $310 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 Truman Annex Shipyard a luxury gated community. No ...
From $310 per night (USD)Expedia
From $1029 per night (USD)VRBO
DOLPHIN WATCH @ 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 $1029 per night (USD)VRBO
From $379 per night (USD)VRBO
AMBERJACK in the Truman Annex
- 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 $379 per night (USD)VRBO
From $821 per night (USD)VRBO
CATCH OF THE DAY in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
View passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former ...
From $821 per night (USD)VRBO
From $307 per night (USD)VRBO
SOUTHARD COMFORT in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOCATION, LOCATION, LOCATION and under new ownership. Southard Comfort is on Southard Street in the TRUMAN ANNEX, which ...
From $307 per night (USD)VRBO
From $97 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 $97 per night (USD)VRBO
From $675 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 $675 per night (USD)Expedia
From $435 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 $435 per night (USD)VRBO
From $999 per night (USD)Expedia
Sunnyside Up- Colorful Home, Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Summary: This charming Key West Conch home is located on United Street on the edge of "Old Town" Key West. The kitchen a ...
From $999 per night (USD)Expedia
From $201 per night (USD)VRBO
South Beachside, Tropical Paradise, Now open Jan 2nd 2023 - Feb 1st
- 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 $201 per night (USD)VRBO
From $200 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 $200 per night (USD)VRBO
From $586 per night (USD)VRBO
PARADISE ON THE OCEAN in the Truman Annex
- 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 $586 per night (USD)VRBO
From $379 per night (USD)VRBO
A SUNRISE COTTAGE in the Truman Annex
- 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 $379 per night (USD)VRBO
From $381 per night (USD)VRBO
Cocktails & Dreams - Updated 2nd Floor Condo, Walk To Duval St, Seaport, Waterpark, Beach & Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Cocktails & Dreams! This updated second floor condo in the Shipyard Condominiums boasts one of the best loca ...
From $381 per night (USD)VRBO
From $336 per night (USD)VRBO
ALMOST PARADISE in the Truman Annex
- 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 $336 per night (USD)VRBO