Skip to content
Sign up
Log in
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.

Family House, 2 K BR's, Private Spa/Deck, 2 pools.
SUPERHOSTEntire 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!

What guests are saying:

“We LOVED our stay here. One block away from Duval Street where all of the restaurants and night life are. We rented bikes and mopeds from the rental company on the corner and they had fantastic deals. Everything is in walking distance, but the area itself is bike friendly so we took our rental bikes everywhere. The actual house is in a little shared courtyard with 4 other rental properties, but you don’t really interact with any of the other guests if you don’t want to. Property was very well kept and clean. Had everything we needed, and if we are ever back in Key West we will definitely look up this property!”

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOSTEntire 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.

What guests are saying:

“It was lovely staying at Harrison’s Hideaway! It was the perfect amount of space for us, lovely finishes, amenities and super clean. Staff greeted us at the front door when we arrived and gave great recommendations for nearby amenities. (There’s a great Cuban coffee place just steps from the front door). It truly was as advertised, a private oasis right in the heart of old town. And that bed is sooo comfortable. More than we would usually spend and it was worth every penny!”

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire 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.

What guests are saying:

“This place is extremely close to Duval street (where the bars are), walking distance to the "90 miles to Cuba" sign, extremely close and within walking distance to a ton of fabulous restaurants. You don't need a car here. The trolley and bus are a block away and it's super easy to use. This place has everything! You only need to bring your toothpaste, toothbrush and clothes. Everything is provided. Think hotel amenites with that home feeling. The staff are helpful, wonderful and absolutely amazing”

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

1 bedroom Cottage
SUPERHOSTEntire apartment
1 bedroom Cottage
Price:$139 / night
Honeymoon Hideaway, King bed, Private Deck & Spa!
SUPERHOSTEntire apartment
Honeymoon Hideaway, King bed, Private Deck & Spa!
Price:$328 / night
The Green House ❀ Garden
SUPERHOSTEntire apartment
The Green House ❀ Garden
Price:$162 / night
Duval Balcony - Suite Mischief
SUPERHOSTEntire apartment
Duval Balcony - Suite Mischief
Price:$133 / night
Starr's Suite - 2 person K Suite w/Private Spa!
SUPERHOSTEntire apartment
Starr's Suite - 2 person K Suite w/Private Spa!
Price:$288 / night
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
Price:$250 / night
Studio Blu
SUPERHOSTEntire apartment
Studio Blu
Price:$158 / night
Duval Balcony - Street Suite
SUPERHOSTEntire apartment
Duval Balcony - Street Suite
Price:$132 / night
Duval Balcony Spanky's Retreat
SUPERHOSTEntire apartment
Duval Balcony Spanky's Retreat
Price:$149 / night
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOSTEntire apartment
Bella Vita - 1B/1B Condo Just Steps from Duval
Price:$199 / night
Old Town Suites - 2 Bedroom Suite
SUPERHOSTEntire apartment
Old Town Suites - 2 Bedroom Suite
Price:$190 / night
KW Luxury 2/2 Beachfront resort  Tropical Oasis
SUPERHOSTEntire apartment
KW Luxury 2/2 Beachfront resort Tropical Oasis
Price:$340 / night
Show all

Pet-friendly houses

Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
SUPERHOSTEntire house
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
Price:$998 / night
Big Blu - 5 bedroom, 4 bath in old town
SUPERHOSTEntire house
Big Blu - 5 bedroom, 4 bath in old town
Price:$716 / night
Lennon's Lodge, Luxury Accommodations for up to 6!
SUPERHOSTEntire house
Lennon's Lodge, Luxury Accommodations for up to 6!
Price:$458 / night
MERMAID COVE- Funky Getaway on Duval
SUPERHOSTEntire house
MERMAID COVE- Funky Getaway on Duval
Price:$895 / night
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
Entire house
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
Price:$795 / 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:$383 / night
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
SUPERHOSTEntire house
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
Price:$3,150 / 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:$673 / night
Royal Escape
SUPERHOSTEntire house
Royal Escape
Price:$632 / night
Casa Cristol
SUPERHOSTEntire house
Casa Cristol
Price:$406 / night
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
SUPERHOSTEntire house
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
Price:$328 / night
Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
Entire house
Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
Price:$811 / night
Show all

Houses with pools

Sunrise Beach Escape
SUPERHOSTEntire house
Sunrise Beach Escape
Price:$280 / night
The Palm Villa, Island Oasis steps from Duval
Entire house
The Palm Villa, Island Oasis steps from Duval
Price:$664 / night
VENTURE OUT  Waterfront with dock/Gated community
Entire house
VENTURE OUT Waterfront with dock/Gated community
Price:$186 / night
Real World MTV House Key West
SUPERHOSTEntire house
Real World MTV House Key West
Price:$2,470 / night
Daisy Space on a Cudjoe Key Canal
SUPERHOSTEntire house
Daisy Space on a Cudjoe Key Canal
Price:$269 / night
Newly Renovated Oceanside House with Pool
SUPERHOSTEntire house
Newly Renovated Oceanside House with Pool
Price:$290 / night
VENTURE OUT 308  WATERFRONT /GATED COMMUNITY
Entire house
VENTURE OUT 308 WATERFRONT /GATED COMMUNITY
Price:$186 / night
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
Entire house
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
Price:$235 / night
OCEAN VIEW PARADISE AT VENTURE OUT + BIKES/KAYAKS
Entire house
OCEAN VIEW PARADISE AT VENTURE OUT + BIKES/KAYAKS
Price:$172 / night
Coral Hammock Poolside House
Entire house
Coral Hammock Poolside House
Price:$318 / night
Secret Villa II
Entire house
Secret Villa II
Price:$1,049 / night
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
SUPERHOSTEntire house
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Price:$1,240 / night
Show all