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Vacation rental houses in Key West

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Top-rated houses in Key West

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

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.
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.
2/2 Old Town Waterfront Condo Pet Friendly
SUPERHOST
Entire residential home · 6 guests · 3 beds · 2 baths
2/2 Old Town Waterfront Condo Pet FriendlyTime to relax! Bring your family & friends to this 1350sqft Waterfront corner unit at Pelican Landing. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Vacation rentals for every style

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Popular house amenities in Key West

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

Apartments in Key West

SUPERHOST
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  2. Key West
Mallory House Room #2
$166 per night
SUPERHOST
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Bella Vita - 1B/1B Condo Just Steps from Duval
$207 per night
  1. Private room
  2. Key West
Unit #14 - The Galleria - 2nd Floor near Duval
$209 per night
SUPERHOST
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  2. Key West
Key West Suites #205
$277 per night
SUPERHOST
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Duval Balcony - Suite Mischief
$311 per night
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  2. Key West
Luxurious Apartment with pool #1
$214 per night
SUPERHOST
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  2. Key West
Key West Suites #202
$322 per night
SUPERHOST
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Duval Balcony Spanky's Retreat
$299 per night
SUPERHOST
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  2. Key West
Duval Balcony - Street Suite
$339 per night
SUPERHOST
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Duval Retreat- Contemporary Duval Street Condo
$543 per night
SUPERHOST
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Honeymoon Hideaway, King bed, Private Deck & Spa!
$468 per night
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  2. Key West
Studio condo w/ entertainment, full kitchen & private parking - central location
$330 per night

Pet-friendly houses

SUPERHOST
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$478 per night
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  2. Key West
Almost Southernmost 2 Bedroom Cottage with private spa
$546 per night
SUPERHOST
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Downtown Waterfront Penthouse Pool, Parking, Dock
$769 per night
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  2. Key West
Charming house w/ private patio - great central location, dogs OK
$469 per night
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  2. Key West
NEW! Poolside Paradise - Updated Home with Heated Pool In Heart of Key West
$1,045 per night
SUPERHOST
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  2. Key West
Private 2BR with Pool in Old Town Key West
$251 per night
  1. Entire residential home
  2. Key West
WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
$550 per night
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  2. Key West
Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
$546 per night
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  2. Key West
Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!
$1,500 per night
SUPERHOST
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Waterfront Oasis! With Boating Access!
$195 per night
SUPERHOST
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Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
$1,308 per night
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  2. Key West
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
$1,052 per night

Houses with pools

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Quaint CasaBianca - The Perfect Old Town Sanctuary
$250 per night
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Luxurious, beautiful house with large pool
$350 per night
SUPERHOST
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Historic Key West - Conch House - Sleeps 5
$656 per night
SUPERHOST
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Historic Key West - Turtle House - Sleeps 6
$842 per night
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  2. Key West
Newly remodeled family home with a shared swimming pool and fitness center!
$557 per night
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  2. Key West
Margarita Cottage-
$198 per night
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  2. Key West
Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
$1,122 per night
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  2. Key West
Coral Hammock Poolside Home
$574 per night
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  2. Key West
Coconut Cabana: A restored Old Town home with charm & tropical ambience
$968 per night
SUPERHOST
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Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
$550 per night
SUPERHOST
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McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
$468 per night
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  2. Key West
Almost Southernmost Too - Cute 3BR Cottage with Sundeck and Heated Pool
$989 per night