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Vacation rental houses in Key West

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.

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.

Family House, 2 K BR's, Private Spa/Deck, 2 pools.
SUPERHOST
Entire house · 6 guests · 3 beds · 1.5 baths

Family House, 2 K BR's, Private Spa/Deck, 2 pools.Family House is decorated in a light, Caribbean motif. It is an historic Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 56” Smart TV. Bring your Netflix, Amazon or other UN and PW for your favorite programming. Bose blue tooth speakers and Alexa Echos. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 8 person Jacuzzi. 2 heated pools!

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOST
Entire house · 4 guests · 2 beds · 1 bath

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a King size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner electric stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular house amenities in Key West

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

Apartments in Key West

Duval Balcony Spanky's Retreat
SUPERHOSTEntire apartment
Duval Balcony Spanky's Retreat
Price:€107 / night
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOSTEntire apartment
Bella Vita - 1B/1B Condo Just Steps from Duval
Price:€170 / night
Duval Balcony - Suite Mischief
SUPERHOSTEntire apartment
Duval Balcony - Suite Mischief
Price:€111 / night
Duval Balcony - Street Suite
SUPERHOSTEntire apartment
Duval Balcony - Street Suite
Price:€115 / night
Studio Blu
SUPERHOSTEntire apartment
Studio Blu
Price:€92 / night
Old Town Suites - 2 Bedroom Suite
SUPERHOSTEntire apartment
Old Town Suites - 2 Bedroom Suite
Price:€138 / night
1 bedroom Cottage
SUPERHOSTEntire apartment
1 bedroom Cottage
Price:€124 / night
Honeymoon Hideaway, King bed, Private Deck & Spa!
SUPERHOSTEntire apartment
Honeymoon Hideaway, King bed, Private Deck & Spa!
Price:€280 / night
KW Luxury 2/2 Beachfront resort  Tropical Oasis
SUPERHOSTEntire apartment
KW Luxury 2/2 Beachfront resort Tropical Oasis
Price:€251 / night
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
Price:€213 / night
The Green House ❀ Garden
SUPERHOSTEntire apartment
The Green House ❀ Garden
Price:€152 / night
Starr's Suite - 2 person K Suite w/Private Spa!
SUPERHOSTEntire apartment
Starr's Suite - 2 person K Suite w/Private Spa!
Price:€280 / night
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Pet-friendly houses

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire house
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Price:€305 / night
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
SUPERHOSTEntire house
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
Price:€424 / night
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOSTEntire house
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Price:€288 / night
Lennon's Lodge, Luxury Accommodations for up to 6!
SUPERHOSTEntire house
Lennon's Lodge, Luxury Accommodations for up to 6!
Price:€390 / night
MERMAID COVE- Funky Getaway on Duval
SUPERHOSTEntire house
MERMAID COVE- Funky Getaway on Duval
Price:€547 / night
Casa Cristol
SUPERHOSTEntire house
Casa Cristol
Price:€376 / night
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
SUPERHOSTEntire house
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
Price:€280 / night
Big Blu - 5 bedroom, 4 bath in old town
SUPERHOSTEntire house
Big Blu - 5 bedroom, 4 bath in old town
Price:€610 / night
Royal Escape
SUPERHOSTEntire house
Royal Escape
Price:€539 / night
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
SUPERHOSTEntire house
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
Price:€850 / night
Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!
Entire house
Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!
Price:€570 / night
Large, dog-friendly home on three secluded acres w/ balconies, deck, views
Entire house
Large, dog-friendly home on three secluded acres w/ balconies, deck, views
Price:€328 / night
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Houses with pools

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire house
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Price:€305 / night
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
SUPERHOSTEntire house
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
Price:€424 / night
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOSTEntire house
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Price:€288 / night
Lennon's Lodge, Luxury Accommodations for up to 6!
SUPERHOSTEntire house
Lennon's Lodge, Luxury Accommodations for up to 6!
Price:€390 / night
Coral Hammock Poolside House
Entire house
Coral Hammock Poolside House
Price:€263 / night
Casa Cristol
SUPERHOSTEntire house
Casa Cristol
Price:€376 / night
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
SUPERHOSTEntire house
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
Price:€280 / night
Daisy Space on a Cudjoe Key Canal
SUPERHOSTEntire house
Daisy Space on a Cudjoe Key Canal
Price:€229 / night
Big Blu - 5 bedroom, 4 bath in old town
SUPERHOSTEntire house
Big Blu - 5 bedroom, 4 bath in old town
Price:€610 / night
Royal Escape
SUPERHOSTEntire house
Royal Escape
Price:€539 / night
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
SUPERHOSTEntire house
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
Price:€850 / night
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
Entire house
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
Price:€183 / night
Show all

Learn more about Key West

What types of vacation rentals are available in Key West?

Here in Key West, there are plenty of options for places to stay. Here are a few examples:
  • Houses (310 rentals)
  • Apartments (149 rentals)
  • Boats (89 rentals)

Are there houses with pools?

Who doesn’t want a pool at their house? Here in Key West, you’ll find 217 houses that have pools.

What are the top attractions in Key West?

Locals agree that these attractions are worth a visit:
  • The Ernest Hemingway Home and Museum (816 rentals)
  • Duval Street (290 rentals)
  • Southernmost Point Of The Continental Us (255 rentals)
  • The Key West Butterfly and Nature Conservatory (288 rentals)
  • Fort Zachary Taylor (24 rentals)

What are some kid-friendly activities in Key West?

Locals agree—these are all great places to take the kids:
  • The Ernest Hemingway Home and Museum
  • Southernmost Point Of The Continental Us
  • The Key West Butterfly and Nature Conservatory
  • Mallory Square
  • Dry Tortugas National Park

What are the top places to eat in Key West?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • Mallory Square
  • Blue Heaven
  • Sloppy Joe's Bar
  • Roostica
  • Santiago's Bodega | Key West