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Vacation rental houses in Key West

Book beachfront vacation rental houses, houseboats, and more on Airbnb

Top-rated houses in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Old Town - Room Opens to Pool and Garden
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Old Town - Room Opens to Pool and GardenLocated in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Waterfront Gem! With Boating access!
SUPERHOST
Entire residential home · 4 guests · 2 beds · 2 baths

Waterfront Gem! With Boating access!7 day rental now available! Enjoy new comfortable waterfront living in a 2 bedroom, 2 bath open floor plan home. Central A/c, full kitchen with microwave, coffee maker, washer/dryer, dinning table sits (6), lots of closet space, master bedroom with private bathroom with walk-in shower. The Waterfront home has a large dock with BBQ Grill, outdoor seating. Spend the day and evening fishing from your dock or enjoy kayaking or paddle boarding activities from your private backyard.

A Little Place in Key West
SUPERHOST
Private room · 1 guest · 1 bed · 1 private bath

A Little Place in Key WestJust one bedroom for a single traveler with a private entry and private bathroom. Luxury finishings, linens, claw foot tub; cable internet, easy parking out-front. Walking distance to beach, cafes and Duval Street life. Max 1 person no exceptions. Cozy private and comfortable.

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Apartments
  • Unique stays

Popular house amenities in Key West

  • Pool
  • Air conditioning
  • Kitchen
  • Wifi
  • Pets allowed

Apartments in Key West

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Dog-friendly studio in historic building w/ shared pool - beach nearby!
R4,027 ZAR per night
SUPERHOST
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Duval Retreat- Contemporary Duval Street Condo
R6,736 ZAR per night
SUPERHOST
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Key West - Sunrise ❀ The Green House
R2,834 ZAR per night
SUPERHOST
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Key West Suites #203
R4,159 ZAR per night
SUPERHOST
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Duval Balcony - Street Suite
R2,830 ZAR per night
SUPERHOST
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Key West Suites #202
R4,159 ZAR per night
SUPERHOST
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Bella Vita - 1B/1B Condo Just Steps from Duval
R3,583 ZAR per night
SUPERHOST
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Key West - Sunset ❀ The Green House
R2,834 ZAR per night
SUPERHOST
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Duval Balcony Spanky's Retreat
R3,083 ZAR per night
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Luxurious upstairs apartment with pool #3
R2,213 ZAR per night
SUPERHOST
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Mile Zero Suite
R2,974 ZAR per night
SUPERHOST
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Key west in town studio with free bikes
R2,265 ZAR per night

Pet-friendly houses

SUPERHOST
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Mango Tree Cottage
R1,460 ZAR per night
SUPERHOST
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
R6,638 ZAR per night
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
R8,261 ZAR per night
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Vacasa | Family and dog-friendly island condo w/ full kitchen and a great location!
R12,568 ZAR per night
SUPERHOST
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Family House, 2 K BR's, Private Spa/Deck, 2 pools.
R8,822 ZAR per night
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Peaceful home w/ yard, hot tub, off street-parking
R2,582 ZAR per night
SUPERHOST
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Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
R6,904 ZAR per night
SUPERHOST
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Clean and Bright Key West Inspired Home/ Nov 3
R2,641 ZAR per night
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Vacasa | Charming house w/ private patio - great central location, dogs OK
R7,051 ZAR per night
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Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
R16,330 ZAR per night
SUPERHOST
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Casa Cristol - Family Friendly Classic KW Charm
R8,259 ZAR per night
SUPERHOST
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**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
R7,228 ZAR per night

Houses with pools

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Key West, Home, Pool and Electric Car!
R1,932 ZAR per night
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Vacasa | Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok
R5,827 ZAR per night
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Coral Hammock Poolside House
R5,827 ZAR per night
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Newly remodeled family home with a shared swimming pool and fitness center!
R8,394 ZAR per night
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Royal Poinciana Cottage-
R3,195 ZAR per night
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Vacasa | Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
R4,426 ZAR per night
SUPERHOST
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LOOK!! Bargain reduced Sept. private pool, wifi.
R7,302 ZAR per night
SUPERHOST
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Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
R5,901 ZAR per night
SUPERHOST
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Historic Key West - Turtle House - Sleeps 6
R11,787 ZAR per night
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Papa's Hideaway - Garden of Eden
R8,430 ZAR per night
SUPERHOST
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McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
R6,904 ZAR per night
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Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
R17,348 ZAR per night

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