Skip to content

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.

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Entire house · 6 guests · 3 beds · 2 baths

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!*ALL NEWLY RENOVATED*PERFECT LOCATION! *35' Seawall *Magnificent newly renovated 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 19 minutes to Key West. Located in the gated community of Venture Out. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Bring Your Boat! 2 BR/2BA Waterfront Paradise!
SUPERHOST
Entire house · 4 guests · 2 beds · 2 baths

Bring Your Boat! 2 BR/2BA Waterfront Paradise!Bring your boat and enjoy the ideal Florida Keys waterfront location! SLACK TIDE is located on Cudjoe Key, on the Atlantic side of the Overseas Highway at mile marker 23. Situated on a 60 ft wide, deep water canal with direct access to the Atlantic Ocean, it's easy to relax and enjoy the incredible open water views and 35 ft of dock space for your boat. We encourage you to use the 2 kayaks and 1 paddle board we keep onsite to explore the gorgeous Florida Keys waters right outside the back door.

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

Get the amount of space that is right for you

  • Houses
  • Apartments
  • Unique stays

Popular house amenities in Key West

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

Apartments in Key West

SUPERHOST
  1. Entire apartment
  2. Key West
Duval Retreat- Contemporary Duval Street Condo
$405 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Mango Hideaway steps off World Famous Duval street
$284 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
$378 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Duval Balcony - Suite Mischief
$385 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Island Color Suite
$250 per night
  1. Entire apartment
  2. Key West
Key West - Sunrise ❀ The Green House
$209 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Key West Suites Hotel -Adam Scott Rote Suite #203
$298 per night
  1. Entire apartment
  2. Key West
Key West - Sunset ❀ The Green House
$198 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Bella Vita - 1B/1B Condo Just Steps from Duval
$200 per night
SUPERHOST
  1. Private room
  2. Key West
The Galleria~Unit 11 -- Recently Remodeled!
$175 per night
  1. Entire apartment
  2. Key West
Luxurious apartment with pool #2
$350 per night
  1. Entire apartment
  2. Key West
Sunshine Suite Condo Enjoy outdoor Hot tub & Pool
$300 per night

Pet-friendly houses

SUPERHOST
  1. Entire house
  2. Cudjoe Key
Cudjoe Key Home with a View
$280 per night
SUPERHOST
  1. Entire house
  2. Upper Sugarloaf Key
Palms Resort at Sugarloaf / Green House
$1,040 per night
SUPERHOST
  1. Entire house
  2. Key West
Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
$257 per night
  1. Entire house
  2. Key West
Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
$863 per night
  1. Entire house
  2. Cudjoe Key
Judy's Place
$175 per night
SUPERHOST
  1. Entire house
  2. Key West
WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
$425 per night
  1. Entire house
  2. Key West
Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
$442 per night
SUPERHOST
  1. Entire house
  2. Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
$388 per night
  1. Entire house
  2. Key West
Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
$171 per night
  1. Entire house
  2. Cudjoe Key
Beautiful & Private Pool with Atlantic Ocean view
$438 per night
SUPERHOST
  1. Entire house
  2. Key West
Casa Cristol - Family Friendly Classic KW Charm
$551 per night
  1. Entire house
  2. Key West
Duval Delight
$604 per night

Houses with pools

SUPERHOST
  1. Entire house
  2. Key West
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
$1,208 per night
SUPERHOST
  1. Private room
  2. Key West
Old Town - Room Opens to Private Pool and Garden
$239 per night
  1. Entire house
  2. Key West
A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly
$787 per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Daisy Space on a Cudjoe Key Canal *Plz read sumry*
$261 per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Newly Renovated Oceanside House with Pool
$315 per night
  1. Entire house
  2. Cudjoe Key
Fabulous Florida Keys!
$215 per night
  1. Entire house
  2. Cudjoe Key
Sunrise Supreme Paradise: your 2bdrm2bath vacation
$199 per night
  1. Entire house
  2. Cudjoe Key
OCEAN VIEW PARADISE AT VENTURE OUT + BIKES/KAYAKS
$249 per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Erin Go "Spaaagh" canal-front mid-rise
$250 per night
SUPERHOST
  1. Entire house
  2. Key West
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
$498 per night
  1. Entire house
  2. Cudjoe Key
Ocean View 2/2 on canal recently refurbished.
$176 per night
SUPERHOST
  1. Entire house
  2. Key West
Robinson Crusoe Cottage
$308 per night

Nearby destinations