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Vacation rental houses in Key West

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Top-rated houses in Key West

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Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
SUPERHOST
Entire house · 6 guests · 3 beds · 2 baths

Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OKTime to relax! Bring your family & friends to this 1350 sqft Waterfront home 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).

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

Old Town - Room Opens to Private 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.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOST
Entire house · 2 guests · 1 bed · 1 bath

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!Romantic Retreat is a free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon, etc. UN/PW). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

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

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Duval Retreat- Contemporary Duval Street Condo
$409 per night
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Key West - Cool Shade ❀ The Green House
$225 per night
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Mango Hideaway steps off World Famous Duval street
$258 per night
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Honeymoon Hideaway, King bed, Private Deck & Spa!
$398 per night
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Duval Balcony - Suite Mischief
$350 per night
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Island Color Suite
$250 per night
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Luxurious apartment with pool
$110 per night
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Key West Suites Hotel -Adam Scott Rote Suite #203
$329 per night
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Bella Vita - 1B/1B Condo Just Steps from Duval
$200 per night
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Mallory House Room #1
$165 per night
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Location, Location, Location! Cute and Convenient!
$105 per night
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The Galleria~Unit 11 -- Recently Remodeled!
$166 per night

Pet-friendly houses

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Sweet Pea Cottage // 3 Bedroom Home located in Old Town!
$203 per night
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Charming house w/ private patio - great central location, dogs OK
$422 per night
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The Eagle’s Nest (w/ heated pool)
$184 per night
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Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
$959 per night
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
$425 per night
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
$495 per night
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Family House, 2 K BR's, Private Spa/Deck, 2 pools.
$528 per night
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$398 per night
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Angela’s Cottage/Private Pool/Pets Welcome/OldTown
$199 per night
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Casa Cristol - Family Friendly Classic KW Charm
$552 per night
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Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
$1,012 per night
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Duval Delight
$591 per night

Houses with pools

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Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
$1,308 per night
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Royal Poinciana Cottage-
$217 per night
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A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly
$847 per night
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Clean and Bright Key West Inspired Home
$155 per night
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Treasure Cove
$325 per night
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HUGE 5/6 with Pool, Beach and Offstreet Parking!
$1,365 per night
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Charming, Dog-Friendly Getaway w/ a Shared Pool, Free WiFi, Private Washer/Dryer
$154 per night
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Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
$179 per night
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Secret Villa II
$951 per night
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Southern Palms
$1,737 per night
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Clean and Relaxing! 3 King Suites! With everything
$600 per night
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Robinson Crusoe Cottage
$247 per night

Top-rated things to do in Key West

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