Key West Rentals
From $1825 per night (USD)VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool / Modern / Balcony over Duval +
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1825 per night (USD)VRBO
From $240 per night (USD)Expedia
**CARSTEN CONCH COTTAGE @ OLD TOWN** Quaint Cottage + LAST KEY SERVICE…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CARSTEN CONCH ...
From $240 per night (USD)Expedia
From $1134 per night (USD)VRBO
Duval Duo- Two Premier Lofts w/ Pvt Balconies!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval D ...
From $1134 per night (USD)VRBO
From $260 per night (USD)Expedia
Clean/stylish Old Town Key West- Walk to Duval
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/1.5 bathroom Key West cottage has all the comforts of home and is the perfect place to relax and enjoy is ...
From $260 per night (USD)Expedia
From $245 per night (USD)VRBO
Old Town- Walk to everything- Banyan tree view
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/1.5 bathroom Key West cottage has all the comforts of home and is the perfect place to relax and enjoy is ...
From $245 per night (USD)VRBO
From $353 per night (USD)Expedia
NEW! Completely Renovated | Close to Everything | Private Courtyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
La Cala is a Newly Renovated Historic Home Situated on a Corner Lot within Walking Distance to Everything you want to Se ...
From $353 per night (USD)Expedia
From $1166 per night (USD)VRBO
GREAT HOME pool, wifi, Truman Annex, steps to Duval, extra cottage, GREAT PRICES
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
You will love our newly renovated 4 BR 3 1/2 bath home. 4th bedroom and a full bath is located in the guest cottage whic ...
From $1166 per night (USD)VRBO
From $586 per night (USD)VRBO
A BIT OF AQUA in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Foundry a Bostonian style, 3 level townhouses that have been refurbished with tropical flair. Vaulted cei ...
From $586 per night (USD)VRBO
From $190 per night (USD)VRBO
The Emelina, Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $190 per night (USD)VRBO
From $450 per night (USD)Expedia
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $450 per night (USD)Expedia
From $510 per night (USD)VRBO
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $510 per night (USD)VRBO
From $249 per night (USD)Expedia
NEW! Charming 'Boho Breeze' Retreat w/ Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $249 per night (USD)Expedia
From $213 per night (USD)VRBO
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $213 per night (USD)VRBO
From $614 per night (USD)VRBO
ISLAND OASIS in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $614 per night (USD)VRBO
From $629 per night (USD)VRBO
Sea Esta Suite- New Kitchen, Rooftop Pool on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This bright, airy home is located right in the middle of all the action on Duval Street. Located on the interse ...
From $629 per night (USD)VRBO
From $143 per night (USD)Expedia
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard and decks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $143 per night (USD)Expedia
From $299 per night (USD)VRBO
NEW Conch Cottage- SunFilled with Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go ...
From $299 per night (USD)VRBO
From $583 per night (USD)Expedia
Enjoy Old Town Key West in this Beautifully furnished house
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $583 per night (USD)Expedia
From $344 per night (USD)VRBO
Yellow 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 $344 per night (USD)VRBO
From $334 per night (USD)Expedia
Blue 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 $334 per night (USD)Expedia
From $329 per night (USD)VRBO
Green 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 $329 per night (USD)VRBO
From $440 per night (USD)Expedia
Home Away From Home-Beautiful Duval Duplex
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Come stay in paradise! Golf cart available for rent! We are perfectly located one block from Duval Street but in a tranq ...
From $440 per night (USD)Expedia
From $399 per night (USD)VRBO
Poolside King Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $399 per night (USD)VRBO
From $419 per night (USD)Expedia
Poolside Queen Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $419 per night (USD)Expedia
From $579 per night (USD)VRBO
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $579 per night (USD)VRBO
From $377 per night (USD)Expedia
Duval Street Suite on Duval Free Parking and Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $377 per night (USD)Expedia
From $467 per night (USD)VRBO
Duval Street Suite full kitchen, parking, & pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $467 per night (USD)VRBO
From $346 per night (USD)Expedia
Duval Street Suites full kitchen, parking, pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Paradise Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic Old T ...
From $346 per night (USD)Expedia
From $346 per night (USD)VRBO
Duval Street Suite full kitchen and pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlookin ...
From $346 per night (USD)VRBO
From $365 per night (USD)Expedia
Duval Street Suite with full kitchen pool, parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duv ...
From $365 per night (USD)Expedia
From $2374 per night (USD)VRBO
6 BR 6 BA Guesthouse Suites on Duval parking, pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $2374 per night (USD)VRBO
From $457 per night (USD)Expedia
VILLA AZURA THE BEST place to be in Key West!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Villa Azura - this is Enjoy this gem on a quiet lane in the award-winning gated community of the Truman An ...
From $457 per night (USD)Expedia
From $340 per night (USD)VRBO
Island Paradise- Home w/ Historic Finishes & Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Beautifully restored historic home located on one of the most desirable and pristine blocks of William Street w ...
From $340 per night (USD)VRBO
From $148 per night (USD)Expedia
NEW MONTHLY RENTAL, Old Town, Newly Furnished, Duplex, month for price of week
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $148 per night (USD)Expedia
From $554 per night (USD)VRBO
Poolside Suite- Bright and Sunny Home with Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $554 per night (USD)VRBO
From $671 per night (USD)VRBO
ABOVE IT ALL in Mills Place in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
IMMACULATE RETREAT STEPS FROM IT updated and redecorated, this beautifully designed and appointed Truman Annex multi-le ...
From $671 per night (USD)VRBO
From $345 per night (USD)VRBO
AWAY FROM IT ALL @ 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 $345 per night (USD)VRBO
From $525 per night (USD)Expedia
Galleon Resort Waterfront Luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $525 per night (USD)Expedia
From $304 per night (USD)VRBO
**PERFECT HARMONY @ MIDTOWN** Home + Pool / Near Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! PERFECT HARMO ...
From $304 per night (USD)VRBO
From $1879 per night (USD)Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1879 per night (USD)Expedia
From $408 per night (USD)VRBO
Samana Cay - Granite Countertops & Pool! Suite 405
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This sea-themed condo provides all of your comforts of home at your fingertips. Feel like a local and enjoy the ...
From $408 per night (USD)VRBO
From $409 per night (USD)Expedia
Grand Turk - Top Floor with Sunset views! Suite 404
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Make the Grand Turk Suite your next home for your family vacation! Including resort amenities find all of your ...
From $409 per night (USD)Expedia
From $1322 per night (USD)VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + 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! Key West is k ...
From $1322 per night (USD)VRBO
From $287 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $287 per night (USD)Expedia
From $290 per night (USD)VRBO
Hydration Station - Single Family Home in Old Town neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This traditional Conch house (shotgun style, single floor) in Old Town has quite a history. It is said to be the first ...
From $290 per night (USD)VRBO
From $275 per night (USD)Expedia
Historic Caroline Street Condo!1 Bedroom 2 Bath, Pool, Amazing Old Town Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history ...
From $275 per night (USD)Expedia
From $199 per night (USD)VRBO
~Galveston Getaway~ Shotgun-style house with Key West vibe and hot tub.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a loca ...
From $199 per night (USD)VRBO
From $405 per night (USD)Expedia
Duval Street Suite full kitchen Old Town with heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $405 per night (USD)Expedia
From $561 per night (USD)VRBO
Ocean Hideaway Key West Retreat Private Nature preserve and Ocean views await
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Where the Ocean Meets the Windswept is nothing like . You don't have to spend a fortune to enjoy a spacious, clean and ...
From $561 per night (USD)VRBO
From $580 per night (USD)Expedia
Catch the sunrise at the complex Shoreline & enjoy the best pool in Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Caribbean Conch is a fantastic rental with a great location in the 1800 Atlantic Condo Complex. This unit features an ex ...
From $580 per night (USD)Expedia
From $375 per night (USD)VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
From $375 per night (USD)VRBO
From $407 per night (USD)Expedia
Trinidad Suite 105 - Pool View & Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Key West has all of your must-sees for a Florida vacation. Just 1 mile away enjoy sun-kissed beaches lapped by ...
From $407 per night (USD)Expedia
From $414 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $414 per night (USD)VRBO
From $223 per night (USD)Expedia
Charming dog-friendly home surrounded by palm trees! Close to attractions!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Barefoot Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $223 per night (USD)Expedia
From $352 per night (USD)VRBO
Classic Dog-Friendly Condo with Shared Pool, Central AC, and High-Speed WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Butterfly Nest 107 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $352 per night (USD)VRBO
From $550 per night (USD)Expedia
The Palms...A beautiful space in the perfect place.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect space in the perfect place. Beautifully renovated two-bedroom on the 2nd floor in the historic Truman Annex ...
From $550 per night (USD)Expedia
From $598 per night (USD)VRBO
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $598 per night (USD)VRBO
From $366 per night (USD)Expedia
Poolside Palms @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $366 per night (USD)Expedia
From $347 per night (USD)VRBO
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** 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! For a month i ...
From $347 per night (USD)VRBO
From $1195 per night (USD)Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + 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! Throughout Ke ...
From $1195 per night (USD)Expedia
From $367 per night (USD)VRBO
Margarita - Bright Condo w/ Pool Access! Suite 305
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Just a short distance from the Key West Airport or right off of US-1 South find comfort in the luxurious living ...
From $367 per night (USD)VRBO
From $291 per night (USD)Expedia
**FAIRWAY TO HEAVEN @ THE GOLF CLUB** Lavish Home + 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! ‘There’s a fe ...
From $291 per night (USD)Expedia
From $613 per night (USD)VRBO
Atocha Cottage- Modern Space w/ Temper-Pedic Beds
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Atocha is part of the newly renovated complex called "Harborwalk Hideaways," located in the Historic Seaport di ...
From $613 per night (USD)VRBO
From $255 per night (USD)Expedia
**PARADISE PERFECTED @ BEACHSIDE** Modern Home / Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden behind ...
From $255 per night (USD)Expedia
From $522 per night (USD)VRBO
Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $522 per night (USD)VRBO
From $302 per night (USD)Expedia
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths. Available May 1st for a 6 month rental 2022. Elegant soph ...
From $302 per night (USD)Expedia
From $230 per night (USD)VRBO
My Florida Escape: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $230 per night (USD)VRBO
From $228 per night (USD)Expedia
**CASTAWAY COTTAGE @ THE GOLF CLUB** Cozy Townhome w/ Community Pool + LAST KEY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASTAWAY COTTA ...
From $228 per night (USD)Expedia
From $2218 per night (USD)VRBO
NEW! Palm Escape - Luxury Home, Pool & Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2218 per night (USD)VRBO
From $350 per night (USD)Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $350 per night (USD)Expedia
From $500 per night (USD)VRBO
Key West Cabana-Old Town Key West- Steps to Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $500 per night (USD)VRBO
From $192 per night (USD)VRBO
CHARMING OLD TOWN CONDO CLOSE TO EVERYTHING
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sunrise @ Southard Square. This lovely townhome community is located in the heart of Old Town and a short str ...
From $192 per night (USD)VRBO
From $324 per night (USD)VRBO
Great Exuma Suite- Sunset view from the 4th Floor!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Great Exuma Suite is located in the beautiful Sunrise Suites Resort community - just a 10 minute drive from Key ...
From $324 per night (USD)VRBO
From $569 per night (USD)Expedia
Happy’s Houseboat Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $569 per night (USD)Expedia
From $275 per night (USD)VRBO
Private Paradise with Heated Waterfall Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $275 per night (USD)VRBO
From $313 per night (USD)Expedia
Bohemian Breeze @ Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $313 per night (USD)Expedia
From $2190 per night (USD)VRBO
FIN & TONIC Waterfront Condo
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $2190 per night (USD)VRBO
From $161 per night (USD)Expedia
Centrally located cottage apartment with patio - walk to beach & dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $161 per night (USD)Expedia
From $223 per night (USD)VRBO
Dog-friendly getaway with furnished patio & shared pool - blocks to the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Conch Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $223 per night (USD)VRBO
From $191 per night (USD)Expedia
Cozy condo with free WiFi & fantastic location in central Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Truman @ Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $191 per night (USD)Expedia
From $234 per night (USD)VRBO
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $234 per night (USD)VRBO
From $1158 per night (USD)VRBO
LADY EMMA in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Lady Emma which is located in the best location in Old Town, the world famous Truman Annex on Emma St. The Tr ...
From $1158 per night (USD)VRBO
From $196 per night (USD)VRBO
~STARFISH~ Spacious and sunny first floor 2B/2BA condo with large pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $196 per night (USD)VRBO
From $270 per night (USD)Expedia
Salida del Sol - Rare Key West Waterfront, Close To Beaches, Duval Street & World Famous Fishing!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Salida del Sol! This luxurious home is one of the few canal front homes located in Key West. You can enjoy a ...
From $270 per night (USD)Expedia
From $275 per night (USD)VRBO
A+ Location in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $275 per night (USD)VRBO
From $914 per night (USD)Expedia
AFTERNOON DELIGHT in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $914 per night (USD)Expedia
From $2878 per night (USD)VRBO
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
- Bedrooms:
- 10
- Bathrooms:
- 8
- Sleeps:
- 20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2878 per night (USD)VRBO
From $1551 per night (USD)Expedia
Luxury Retreat at the Truman Annex near Duval & Beach with Pool, Patio, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Admirals Gold Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1551 per night (USD)Expedia
From $208 per night (USD)VRBO
Julia's Secret
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $208 per night (USD)VRBO
From $293 per night (USD)Expedia
**BIRD of PARADISE** Elegant Home & 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! Like witnessi ...
From $293 per night (USD)Expedia
From $1406 per night (USD)VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1406 per night (USD)VRBO
From $1840 per night (USD)Expedia
Banana's Foster Guest House w/ Heated Pool
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $1840 per night (USD)Expedia
From $499 per night (USD)VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $499 per night (USD)VRBO
From $257 per night (USD)Expedia
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $257 per night (USD)Expedia
From $2310 per night (USD)VRBO
4 The Lifestyle 2 Queens Rooms at The Gates Hotel Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $2310 per night (USD)VRBO
From $561 per night (USD)VRBO
Standard 2 Queens Room at The Gates Hotel Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $561 per night (USD)VRBO
From $1732 per night (USD)VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1732 per night (USD)VRBO
From $423 per night (USD)VRBO
Key West Getaway! Outdoor Pool, Pet-Friendly, Minutes from Key West Lighthouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $423 per night (USD)VRBO
From $497 per night (USD)VRBO
Welcome to Paradise! Lavish and Relaxing. Enjoy the On-site Pool, Restaurant
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $497 per night (USD)VRBO
From $1149 per night (USD)VRBO
Escape to the Keys! 2 Serene Units, Pool, Restaurant, On-Site Bar, Gym, Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1149 per night (USD)VRBO