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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.

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.
Get Away
Private room · 2 guests · 1 bed · 1 private bath
Get AwayProperty Location - When you stay at Getaway and Va cay in Paradise you will be on the beach and Key West downtown within minutes. Airport and popular locations are near by. The Room - Make yourself at home with central AC, TV, internet access, and cable programming for your entertainment.
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

Get the amount of space that is right for you

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Popular house amenities in Key West

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

Apartments in Key West

SUPERHOST
  1. Private room
  2. Key West
Mallory House Room #2
$175 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Key West Suites #201
$365 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Duval Balcony - Street Suite
$496 per night
  1. Entire rental unit
  2. Key West
Luxurious upstairs apartment with pool #3
$199 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Duval Balcony - Suite Mischief
$336 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Duval Balcony Spanky's Retreat
$362 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Bella Vita - 1B/1B Condo Just Steps from Duval
$291 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Key West Suites #202
$404 per night
  1. Private room
  2. Key West
The Galleria~Unit #14 - Recently Remodeled!
$220 per night
  1. Entire rental unit
  2. Key West
Studio condo w/ entertainment, full kitchen & private parking - central location
$332 per night
SUPERHOST
  1. Entire rental unit
  2. Key West
Duval Retreat- Contemporary Duval Street Condo
$629 per night
  1. Entire rental unit
  2. Key West
Key West - Sunset ❀ The Green House
$296 per night

Pet-friendly houses

SUPERHOST
  1. Entire residential home
  2. Key West
Waterfront Oasis! With Boating Access!
$195 per night
  1. Entire residential home
  2. Key West
WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
$693 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Casa Cristol - Family Friendly Classic KW Charm
$576 per night
  1. Entire residential home
  2. Key West
Charming house w/ private patio - great central location, dogs OK
$483 per night
  1. Entire residential home
  2. Key West
Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
$566 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$451 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Private 2BR with Pool in Old Town Key West
$351 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$468 per night
  1. Entire residential home
  2. Key West
Porchside Paradise
$356 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Downtown Waterfront Penthouse Pool, Parking, Dock
$1,071 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Lennon's Lodge, Luxury Accommodations for up to 6!
$579 per night
  1. Entire residential home
  2. Key West
Dog-friendly Key West cottage with a private hot tub & an unbeatable location!
$858 per night

Houses with pools

SUPERHOST
  1. Entire residential home
  2. Key West
Waterfront Oasis! With Boating Access!
$195 per night
  1. Entire residential home
  2. Key West
WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
$693 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Casa Cristol - Family Friendly Classic KW Charm
$576 per night
  1. Entire residential home
  2. Key West
Charming house w/ private patio - great central location, dogs OK
$483 per night
  1. Entire residential home
  2. Key West
Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
$566 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$451 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Private 2BR with Pool in Old Town Key West
$351 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$468 per night
  1. Entire residential home
  2. Key West
Porchside Paradise
$356 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Downtown Waterfront Penthouse Pool, Parking, Dock
$1,071 per night
SUPERHOST
  1. Entire residential home
  2. Key West
Lennon's Lodge, Luxury Accommodations for up to 6!
$579 per night
  1. Entire residential home
  2. Key West
Dog-friendly Key West cottage with a private hot tub & an unbeatable location!
$858 per night