Key West Rentals
- From $498 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 $498 per night (USD)VRBO
- From $245 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 $245 per night (USD)Expedia
- From $1029 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 $1029 per night (USD)VRBO
- From $379 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 $379 per night (USD)Expedia
- From $821 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 $821 per night (USD)VRBO
- From $364 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 $364 per night (USD)Expedia
- From $121 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 $121 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 $332 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 $332 per night (USD)VRBO
- From $668 per night (USD)
Expedia
Sunnyside Up by Brightwild | Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Summary: This charming Key West conch home is situated on United Street, on the edge of "Old Town" Key West. The kitchen ...
From $668 per night (USD)Expedia
- From $586 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 $586 per night (USD)VRBO
- From $379 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 $379 per night (USD)Expedia
- From $325 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 $325 per night (USD)VRBO
- From $336 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 $336 per night (USD)Expedia
- From $1641 per night (USD)
VRBO
The Curry House by Brightwild | 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 $1641 per night (USD)VRBO
- From $227 per night (USD)
Expedia
Curry House #6 by Brightwild | King Bed, 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 $227 per night (USD)Expedia
- From $384 per night (USD)
VRBO
Curry House by Brightwild | Balcony & Pool -Rm 3&4
- 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 $384 per night (USD)VRBO
- From $245 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 $245 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Curry House #8 by Brightwild | King Bed, 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 $219 per night (USD)VRBO
- From $233 per night (USD)
Expedia
Curry House #7 by Brightwild | King Bed, 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 $233 per night (USD)Expedia
- From $222 per night (USD)
VRBO
Curry House #2 by Brightwild | 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 $222 per night (USD)VRBO
- From $207 per night (USD)
Expedia
Curry House by Brightwild | Heated Pool - Rm #9
- 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 $207 per night (USD)Expedia
- From $245 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 $245 per night (USD)VRBO
- From $165 per night (USD)
Expedia
**PAINTED SKY @ 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! With a backdr ...
From $165 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Sweet Caroline by Brightwild | Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $476 per night (USD)VRBO
- From $235 per night (USD)
Expedia
Key Lime Cottage by Brightwild | Pool & 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 $235 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Sugar Pie Suite by Brightwild | 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 $201 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Honey Bun Hideaway by Brightwild | 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 $202 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Banana Split by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $250 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Creme Brulee Suite by Brightwild | 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 $211 per night (USD)Expedia
- From $165 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 $165 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $429 per night (USD)
VRBO
COLORFUL COCKTAIL at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $429 per night (USD)VRBO
- From $729 per night (USD)
Expedia
**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 $729 per night (USD)Expedia
- From $557 per night (USD)
VRBO
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 $557 per night (USD)VRBO
- From $256 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 $256 per night (USD)VRBO
- From $141 per night (USD)
VRBO
Colorful beachfront condo w\/ ocean view balcony & shared hot tub\/pool\/tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $141 per night (USD)VRBO
- From $175 per night (USD)
Expedia
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 $175 per night (USD)Expedia
- From $379 per night (USD)
VRBO
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 $379 per night (USD)VRBO
- From $295 per night (USD)
Expedia
**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 30 days prior to your arrival! You don’t oft ...
From $295 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $240 per night (USD)
Expedia
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 ...
From $240 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $431 per night (USD)
Expedia
~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 $431 per night (USD)Expedia
- From $152 per night (USD)
VRBO
Escape the Snow - Paradise awaits. A month in Key West Jan 15th- Feb 18th 22
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located facing the tranquil lush courtyard at 1800 Atlantic. This spacious family retreat features a renovated kitchen. ...
From $152 per night (USD)VRBO
- From $523 per night (USD)
Expedia
**THE BEAMING BARRACUDA @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERV
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...
From $523 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Hyatt Beach House! Quiet Key West Location! Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $465 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $550 per night (USD)Expedia
- From $460 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $460 per night (USD)VRBO
- Click For Pricing
Expedia
Studio at Hyatt Residence Club Key West, Sunset Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Seth Nock Licensed Broker, Selling Timeshares INC. Studio at Hyatt Residence Club Key West, Sunset Harbor. Check-in: ...
Click For PricingExpedia
- From $250 per night (USD)
VRBO
Anchors Away - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $250 per night (USD)VRBO
- From $250 per night (USD)
Expedia
TAILGATE KEY at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $250 per night (USD)Expedia
- From $436 per night (USD)
VRBO
SWEET'S SPOT at The Truman Annex in Key West
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $436 per night (USD)VRBO
- From $317 per night (USD)
Expedia
Red Room at Grand Maloney Hotel with Pool!
- 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 $317 per night (USD)Expedia
- From $184 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $184 per night (USD)VRBO
- From $307 per night (USD)
Expedia
BEST TIME at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This Shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and e ...
From $307 per night (USD)Expedia
- From $649 per night (USD)
VRBO
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $649 per night (USD)VRBO
- From $296 per night (USD)
Expedia
African Queen by Brightwild | GREAT Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: African Queen Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seapo ...
From $296 per night (USD)Expedia
- From $309 per night (USD)
VRBO
Pilar's Cottage by Brightwild | Studio w\/Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Pilar Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport distr ...
From $309 per night (USD)VRBO
- From $1284 per night (USD)
Expedia
Harborwalk Hideaways by Brightwild |Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $1284 per night (USD)Expedia
- From $350 per night (USD)
VRBO
POOLSIDE HANGOVER at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away ...
From $350 per night (USD)VRBO
- From $775 per night (USD)
Expedia
Windsor Townhome #4- 3 bedroom 3.5 bath with private pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
From $775 per night (USD)Expedia
- From $1157 per night (USD)
VRBO
A Place on Emma at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1157 per night (USD)VRBO
- From $260 per night (USD)
Expedia
A DUCK ON THE GREEN at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $260 per night (USD)Expedia
- From $307 per night (USD)
VRBO
SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $307 per night (USD)VRBO
- From $335 per night (USD)
Expedia
Road's End by Brightwild | Steps to Duval St!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Just a stone's throw away from Mile Marker Zero lies the aptly named "Road's End," a charming 1 Bd, 1.5 Bth tow ...
From $335 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed an ...
From $150 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Margaretaville," your quintessential Key West getaway that offers you the chance to experience life as a loc ...
From $230 per night (USD)Expedia
- From $383 per night (USD)
VRBO
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w\/ pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $383 per night (USD)VRBO
- From $1563 per night (USD)
Expedia
Captain's Daughter: Oversized home for the whole family w\/private pool & dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1563 per night (USD)Expedia
- From $364 per night (USD)
VRBO
HIGH TIDE at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $364 per night (USD)VRBO
- From $252 per night (USD)
Expedia
SHELLABRATION at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY***** This prime two bedroom, two and a half bath fully furnished ...
From $252 per night (USD)Expedia
- From $350 per night (USD)
VRBO
A CONCH ESCAPE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $350 per night (USD)VRBO
- From $336 per night (USD)
Expedia
A SUNSET VIEW at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
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)Expedia
- Click For Pricing
VRBO
GYPSY'S PALACE at The Truman Annex in Key West - Stunning ocean views!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
Click For PricingVRBO
- From $623 per night (USD)
Expedia
Spacious home with pool & balcony - 1 block from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $623 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Charming home in Old Town, walk to shops & restaurants - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gingerbread Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $156 per night (USD)VRBO
- From $379 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $379 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Old Town Charm Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
From $250 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Location, Beauty & Comfort @ Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $360 per night (USD)Expedia
- From $550 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & 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! Like many of ...
From $550 per night (USD)VRBO
- From $799 per night (USD)
Expedia
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $799 per night (USD)Expedia
- From $334 per night (USD)
VRBO
Alluring corner unit w\/ full kitchen & pool - close to beach\/ nightlife
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $334 per night (USD)VRBO
- From $206 per night (USD)
Expedia
Wonderful Condo in Key West w\/Free WiFi, Lanai, A\/C, Shared Hot Tub & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tradewinds at Smathers Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $206 per night (USD)Expedia
- From $407 per night (USD)
VRBO
Sky Loft by Brightwild | Penthouse in Prime Spot!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This gem of a top floor apartment is perfect for your weekend getaway. Sky Loft is located just one block away ...
From $407 per night (USD)VRBO
- Click For Pricing
Expedia
VILLA ALBA at Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy sunny and beautiful Key West at Villa Alba. Start your day watching the sunrise with your first cup of c ...
Click For PricingExpedia
- From $208 per night (USD)
VRBO
Claude Monet Suite by Brightwild | Pool & Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to the Claude Monet Suite! This colorful, tropically-themed 1st floor suite is tucked away in The Galle ...
From $208 per night (USD)VRBO
- From $736 per night (USD)
Expedia
BLUE LAGOON at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $736 per night (USD)Expedia
- From $228 per night (USD)
VRBO
**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private 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! Look for the ...
From $228 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Banyan Resort - 2 Blocks to Sunset Celebration
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed ...
From $375 per night (USD)Expedia
- From $757 per night (USD)
VRBO
ARCHIPELAGO at The Truman Annex in Key West
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $757 per night (USD)VRBO
- From $586 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $586 per night (USD)Expedia
- From $586 per night (USD)
VRBO
AQUA BREEZE at 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 $586 per night (USD)VRBO
- From $473 per night (USD)
Expedia
Hidden Beach Unit 1. The perfect place to stay in Key West for less
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $473 per night (USD)Expedia
- From $307 per night (USD)
VRBO
SHADY NOOK at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $307 per night (USD)VRBO
- From $202 per night (USD)
Expedia
A PALM TREE PARADISE @ the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $202 per night (USD)Expedia
- From $307 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
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 $585 per night (USD)
Expedia
THE PLANTATION at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $585 per night (USD)Expedia
- From $821 per night (USD)
VRBO
A GULFSTREAM DRIFT at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $821 per night (USD)VRBO
- From $429 per night (USD)
Expedia
LIFE IN THE SLOW LANE at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $429 per night (USD)Expedia