Villa vacation rentals in Key West
Find and book unique villas on Airbnb
Top-rated villa rentals in Key West
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West villa rentals
Villa rentals with a pool
Villa in Key West
4.52 out of 5 average rating, 27 reviewsPilar's Cottage by Brightwild | Studio w/Pool!
Jul 5 – 12
Villa in Marathon
5.0 out of 5 average rating, 7 reviewsThe Peninsular House
Oct 12 – 19
Villa in Marathon
4.88 out of 5 average rating, 32 reviewsCanal Front, Tiki Hut, Kayaks, Bikes, Pool, Beach!
Sep 24 – Oct 1
Villa in Marathon
5.0 out of 5 average rating, 15 reviewsIndigo Reef water view Villa- #1 Guest Favorite
Jan 2 – 9
Villa in Islamorada
5.0 out of 5 average rating, 27 reviewsAnglers Reef Islamorada
Apr 18 – 25
Villa in Marathon
4.73 out of 5 average rating, 33 reviewsPrivate Pool and Dock, Canal Front, Bikes, Beach!
Nov 24 – Dec 1
Villa in Marathon
5.0 out of 5 average rating, 5 reviewsWaterfront Villa (38) w/ sunset views & boat slip
Aug 31 – Sep 7
Villa in Marathon
4.86 out of 5 average rating, 7 reviewsFlorida Keys Wellness Gem Tranquility & Activity
Aug 23 – 30
Beachfront villa rentals
Villa in Marathon
4.81 out of 5 average rating, 31 reviewsBeautiful 3 bedroom house with loft, pool and dock
Nov 2 – 9
Villa in Marathon
4.61 out of 5 average rating, 46 reviewsParadise Duck Key Villa 2B/1.5B
Mar 8 – 15
Villa in Islamorada
5.0 out of 5 average rating, 18 reviewsBayside Villa in Islamorada
Oct 19 – 26
Villa in Cudjoe Key
5.0 out of 5 average rating, 13 reviewsHoward House on the Sea
Sep 29 – Oct 6
Villa in Duck Key
Florida Keys | Exclusive Resort Amenities | 2BR
Sep 7 – 14
Villa in Marathon
Refreshed & Elevated Indigo Reef Luxury Villa 15
Aug 10 – 17
Villa in Cudjoe Key
Key West Paradise w/ Private Pool + Ocean View
Oct 27 – Nov 3
Place to stay in Islamorada
Paradise Found! Outdoor Pool, Pets Allowed!
Dec 16 – 23
Private villa rentals
Villa in Marathon
5.0 out of 5 average rating, 6 reviewsTranquil Ocean View Villa with relaxing tiki
Mar 27 – Apr 3
Villa in Marathon
4.38 out of 5 average rating, 8 reviewsIt's all here for you. Sunsets, snorkeling, swimming, kayaking. See dolphins, turtles and manatees off the back deck
Dec 5 – 12
Villa in Islamorada
Conch Villa 6
May 17 – 24
Villa in Marathon
The Salty Mermaid 4BR/3BA Anglers at Sombrero Beach with Private Pool and Dockage
Feb 16 – 23
Villa in Marathon
4.86 out of 5 average rating, 83 reviewsVilla 5023 on Duck Key BOAT SLIP available
Sep 22 – 29
Villa in Marathon
5.0 out of 5 average rating, 8 reviewsWaterfront Home w/Dock, Pool, Bikes & SO MUCH MORE
Oct 16 – 23
Villa in Duck Key
4.86 out of 5 average rating, 85 reviewsWaterfront villa for families * Family friendly*
Aug 29 – Sep 5
Villa in Duck Key
4.77 out of 5 average rating, 39 reviewsVilla 5086 on Duck Key BOAT SLIP available
May 11 – 18
Quick stats about villa rentals in Key West
Total rentals
10 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
230 reviews
Nightly prices starting at
$280 before taxes and fees
Destinations to explore
- Varadero Vacation rentals
- Havana Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Villa rentals United States
- Beach condo rentals Key West
- Rentals with beach access Key West
- Bungalow rentals Key West
- Rentals with breakfast Key West
- Family-friendly rentals Key West
- Waterfront rentals Key West
- Rentals with a hot tub Key West
- Rentals with an EV charger Key West
- Rentals with a washer and dryer Key West
- Pet-friendly rentals Key West
- Townhouse rentals Key West
- Beach house rentals Key West
- Rentals with a patio Key West
- Fitness-friendly rentals Key West
- Monthly Rentals Key West
- Cottage rentals Key West
- Rentals with pools Key West
- Beachfront rentals Key West
- Rentals with outdoor seating Key West
- Rentals with a fire pit Key West
- Cabin rentals Key West
- Apartment rentals Key West
- Mansion rentals Key West
- Kid-friendly rentals Key West
- Rentals with an accessible height toilet Key West
- Rentals with a kayak Key West
- Condo rentals Key West
- House rentals Key West
- Villa rentals Florida
- Villa rentals Florida Keys
- Villa rentals Marco Island
- Villa rentals Monroe County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom