Resort vacation rentals in Key West
Find and book unique resort rentals on Airbnb
Top-rated resort rentals in Key West
Guests agree: these resort rentals are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 2 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West resort rentals
Family-friendly resort rentals
Resort in Key West
4.83 out of 5 average rating, 12 reviews1BR Condo Banyan Tree, KeyWest Unit 505/701
JulieRating, 5 stars27 months ago
Fantastic location… walked everywhere! Enjoyed the pool and tiki area and the pathway, trees and foliage just gorgeous. I’m a sucker for a spiral staircase so loved the interior! We had everything we needed.
Resort in Key West
4.67 out of 5 average rating, 9 reviewsStudio#202CondoBanyan Tree Key West
MelissaRating, 5 stars29 months ago
WOW! I was so impressed with the amenities and the location of this place. I would most definitely try to stay here again the next time I come to Key West. Such a good location. So close to all the fun. A short bike ride away from EVERYTHING. The regulars at the resort were a blast too. Everyone was so nice and friendly.
Resort in Key West
5 out of 5 average rating, 5 reviewsThe Galleon, Key West
KimmyRating, 5 stars6 months ago
We have been visiting key west for 25+ years and always stay at the galleon. There is no better place in key west. You arrive park your car and can walk to everything for your entire stay. We will absolutely be back. Thanks Roger for a smooth booking process.
Resort in Key West
4.88 out of 5 average rating, 16 reviews1BR #405 Banyan Resort Key West, FL
KimRating, 5 stars1 month ago
Great location! Enjoyed the beauty of the banyan trees.
Resort rentals with a pool
Resort in Key West
4.83 out of 5 average rating, 12 reviews1BR Condo Banyan Tree, KeyWest Unit 505/701
JulieRating, 5 stars27 months ago
Fantastic location… walked everywhere! Enjoyed the pool and tiki area and the pathway, trees and foliage just gorgeous. I’m a sucker for a spiral staircase so loved the interior! We had everything we needed.
Resort in Key West
4.73 out of 5 average rating, 52 reviewsCharming 2 Bedroom Suite Beach Resort
MichaelRating, 5 stars3 months ago
Great spot. Will definitely try and book here again my next time in Key West. Beach /pool/spa was the cherry on top. 10/10.
Resort in Key West
4.88 out of 5 average rating, 16 reviews1BR #405 Banyan Resort Key West, FL
KimRating, 5 stars1 month ago
Great location! Enjoyed the beauty of the banyan trees.
Superhost
Resort in Key West
4.89 out of 5 average rating, 9 reviewsParrot's Perch
JonathanRating, 5 stars10 months ago
easy walk to everything and housekeeping daily was nice.
Resort in Key West
5 out of 5 average rating, 4 reviewsHyatt Windward Pointe - Key West - Amazing Resort!
DonnaRating, 5 stars33 months ago
Resort was great. Fun location, beautiful room. Cleaning service or restocking of items was slow and needed to be scheduled at least 24 hours in advance. But overall an amazing time and great spot.
Superhost
Resort in Key West
4.8 out of 5 average rating, 10 reviewsKatie's Kottage
AmyRating, 5 stars5 months ago
What a great stay! First impression, this place looks exactly like the pictures but was much smaller than I was expecting. The sofa bed is also a tiny bit short for two taller people (designed for 5’ 8” or under, I’d say). That said, it was overall the perfect stay for our family of six + an infant! The location is ideal no matter where you want to go in Key West. We walked to many restaurants and local attractions, but could’ve truthfully spent our entire stay in the pools. The stay felt private and comfortable. The location, amenities, and price make this stay unmatched. Thoughtful touches like breakfast in the gazebo were an added treat. Cleaning staff came daily and refreshed the space. We truly loved this space and would definitely stay here again!
Resort rentals with a gym
Quick stats about resort rentals in Key West
Total rentals
50 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
150 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Florida Keys Vacation rentals
- Havana Vacation rentals
- Miami Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Kissimmee Vacation rentals
- Four Corners Vacation rentals
- Resort rentals United States
- Resort rentals Florida
- Townhouse rentals Key West
- Beach house rentals Key West
- Rentals with a hot tub Key West
- Rentals with a washer and dryer Key West
- Rentals with breakfast Key West
- Rentals with an EV charger Key West
- Luxury rentals Key West
- Villa rentals Key West
- Beachfront rentals Key West
- Family-friendly rentals Key West
- Rentals with pools Key West
- Houseboat rentals Key West
- Mansion rentals Key West
- Pet-friendly rentals Key West
- Rentals with a patio Key West
- Beach condo rentals Key West
- Fitness-friendly rentals Key West
- Condo rentals Key West
- Waterfront rentals Key West
- Rentals with a kayak Key West
- Kid-friendly rentals Key West
- Rentals with a fireplace Key West
- Monthly Rentals Key West
- Rentals with an accessible height toilet Key West
- Cottage rentals Key West
- Apartment rentals Key West
- Rentals with lake access Key West
- Hotel rentals Key West
- House rentals Key West
- Rentals with a fire pit Key West
- Rentals with beach access Key West
- Rentals with outdoor seating Key West
- Resort rentals Miami-Dade County
- Resort rentals Florida Keys
- Resort rentals Monroe County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Sports activities United States
- Wellness United States
- Entertainment United States
- Nature and outdoors United States
- Art and culture United States
- Things to do Florida
- Art and culture Florida
- Wellness Florida
- Entertainment Florida
- Sightseeing Florida
- Food and drink Florida
- Sports activities Florida
- Nature and outdoors Florida
- Things to do Monroe County
- Sightseeing Monroe County
- Nature and outdoors Monroe County
- Food and drink Monroe County
- Entertainment Monroe County
- Sports activities Monroe County
- Art and culture Monroe County
- Things to do Key West
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes