Key West Rentals
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 $392 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 $392 per night (USD)Expedia
From $925 per night (USD)VRBO
Island Time | Gorgeous Condo, Steps To The Beach!
- 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 $925 per night (USD)VRBO
From $560 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 $560 per night (USD)Expedia
From $1321 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 $1321 per night (USD)VRBO
From $401 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 $401 per night (USD)Expedia
Click For PricingVRBO
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 $654 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 $654 per night (USD)VRBO
From $1710 per night (USD)VRBO
Southern Palms | Pool & Parking
- 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 $1710 per night (USD)VRBO
From $486 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 $486 per night (USD)Expedia
From $727 per night (USD)VRBO
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 $727 per night (USD)VRBO
From $490 per night (USD)Expedia
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 $490 per night (USD)Expedia
From $574 per night (USD)VRBO
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 $574 per night (USD)VRBO
From $814 per night (USD)VRBO
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 $814 per night (USD)VRBO
From $1613 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 $1613 per night (USD)VRBO
From $1131 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 $1131 per night (USD)VRBO
From $1612 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 $1612 per night (USD)VRBO
From $892 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 $892 per night (USD)VRBO
From $2149 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 $2149 per night (USD)VRBO
From $987 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 $987 per night (USD)VRBO
From $2262 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 $2262 per night (USD)VRBO
From $1392 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 $1392 per night (USD)VRBO
From $1505 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 $1505 per night (USD)VRBO
From $1074 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 $1074 per night (USD)VRBO
From $2006 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 $2006 per night (USD)VRBO
From $1397 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 $1397 per night (USD)VRBO
From $1302 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 $1302 per night (USD)VRBO
From $1650 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 $1650 per night (USD)VRBO
From $900 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 $900 per night (USD)VRBO
From $1911 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 $1911 per night (USD)VRBO
From $534 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 $534 per night (USD)VRBO
From $429 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 $429 per night (USD)VRBO
From $528 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 $528 per night (USD)VRBO
From $478 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 $478 per night (USD)VRBO
From $503 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 $503 per night (USD)VRBO
From $867 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 $867 per night (USD)VRBO
From $486 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 $486 per night (USD)VRBO
From $432 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 $432 per night (USD)VRBO
From $489 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 $489 per night (USD)VRBO
From $465 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 $465 per night (USD)VRBO
Click For PricingVRBO
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 PricingVRBO
From $441 per night (USD)Expedia
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 $441 per night (USD)Expedia
From $360 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 $360 per night (USD)VRBO
From $365 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 $365 per night (USD)Expedia
From $276 per night (USD)VRBO
Unique Home with loft @ Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $276 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 in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $419 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 $419 per night (USD)Expedia
From $404 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 $404 per night (USD)VRBO
From $462 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 $462 per night (USD)Expedia
From $485 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 $485 per night (USD)VRBO
From $615 per night (USD)Expedia
Classic Key West condo w\/ private parking, covered porches, & shared pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $615 per night (USD)Expedia
From $531 per night (USD)VRBO
**LAYOVER in PARADISE @ CASA MARINA** New 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! A home design ...
From $531 per night (USD)VRBO
From $592 per night (USD)Expedia
AAH PARADISE at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
AAH PARADISE This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been r ...
From $592 per night (USD)Expedia
From $477 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 $477 per night (USD)VRBO
From $694 per night (USD)Expedia
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 $694 per night (USD)Expedia
From $1332 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 $1332 per night (USD)VRBO
From $276 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 $276 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 $588 per night (USD)Expedia
AMBERJACK at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $588 per night (USD)Expedia
From $1018 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 $1018 per night (USD)VRBO
From $447 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 $447 per night (USD)Expedia
From $309 per night (USD)VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $309 per night (USD)VRBO
From $855 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 $855 per night (USD)Expedia
From $730 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 $730 per night (USD)VRBO
From $761 per night (USD)Expedia
Sunnyside Up | Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
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 $242 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 $242 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 $765 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 $765 per night (USD)VRBO
From $499 per night (USD)Expedia
A SUNRISE COTTAGE at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $499 per night (USD)Expedia
From $428 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 $428 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
From $5532 per night (USD)VRBO
The Curry House, Downtown | Historic Guesthome
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $5532 per night (USD)VRBO
From $338 per night (USD)Expedia
Curry House #6 | King Bed & Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guest ...
From $338 per night (USD)Expedia
From $517 per night (USD)VRBO
Curry House Room 3&4 | Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $517 per night (USD)VRBO
From $320 per night (USD)Expedia
Curry House Room 1 | Heated Pool & Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $320 per night (USD)Expedia
From $299 per night (USD)VRBO
Curry House #8 | King Bed, Pool & Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $299 per night (USD)VRBO
From $312 per night (USD)Expedia
Curry House #7 | King Bed and Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $312 per night (USD)Expedia
From $329 per night (USD)VRBO
Curry House #2 | Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $329 per night (USD)VRBO
From $276 per night (USD)Expedia
Curry House Room 9 | Little Room & Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $276 per night (USD)Expedia
From $321 per night (USD)VRBO
Curry House Room 5 | King Bed, 1st Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $321 per night (USD)VRBO
From $658 per night (USD)Expedia
Sweet Caroline | Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $658 per night (USD)Expedia
From $353 per night (USD)VRBO
Key Lime Cottage | Pool, Parking, Steps to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $353 per night (USD)VRBO
From $327 per night (USD)Expedia
Sugar Pie Suite | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $327 per night (USD)Expedia
From $318 per night (USD)VRBO
Honey Bun Hideaway | Heated Pool, Steps to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $318 per night (USD)VRBO
From $431 per night (USD)Expedia
Banana Split | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $431 per night (USD)Expedia
From $357 per night (USD)VRBO
Creme Brulee Suite | Steps to Duval, Pvt Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $357 per night (USD)VRBO
From $664 per night (USD)Expedia
COLORFUL COCKTAIL in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This Shipyard unit is a two level condominium which has a private courtyard with a deck to enjoy the beautiful weather a ...
From $664 per night (USD)Expedia
From $1351 per night (USD)VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + LAST KEY SERVICES
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When explorin ...
From $1351 per night (USD)VRBO
From $830 per night (USD)Expedia
A PALM OASIS at The Truman Annex in Key West.....
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
NEW LISTING!!! This charming two bedroom, two and one half bath townhome has recently been updated and added to our rent ...
From $830 per night (USD)Expedia
From $460 per night (USD)VRBO
Coastal Inspired Cottage in Bahama Village Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...
From $460 per night (USD)VRBO
From $977 per night (USD)Expedia
Colorful beachfront condo w\/ ocean view balcony & shared hot tub\/pool\/tennis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $977 per night (USD)Expedia
From $353 per night (USD)VRBO
Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Key Rest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $353 per night (USD)VRBO
From $233 per night (USD)Expedia
MONTHLY RENTAL, block to Duval, POOL, your own personal resort, 3 BR\/ 3 BA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...
From $233 per night (USD)Expedia
From $451 per night (USD)VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $451 per night (USD)VRBO
From $450 per night (USD)Expedia
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...
From $450 per night (USD)Expedia
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FORE REEL at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fore Reel! Have you ever dreamed of living in a quaint Key West Golfing gated community with so many wonderfu ...
Click For PricingExpedia
From $339 per night (USD)Expedia
ISLAND TIME at Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Island Time***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome back ...
From $339 per night (USD)Expedia
From $866 per night (USD)VRBO
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block t ...
From $866 per night (USD)VRBO
From $177 per night (USD)Expedia
Extended Summer Stays for 2024 available now
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located facing the tranquil lush courtyard at 1800 Atlantic. This spacious family retreat features a renovated kitchen. ...
From $177 per night (USD)Expedia