
Resort holiday rentals in Key West
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Top-rated resort rentals in Key West
Guests agree: these resort rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for resort rentals in Key West
Family-friendly resort rentals

Studio#202CondoBanyan Tree Key West
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.

Key Largo Cottages w/ Free Sailboat, Kayaks + More
This cottage is in an ideal spot in Key Largo. The amenities here are outstanding - two docks, snorkel gear, kayaks, stand-up paddle boards, and sailing! Great restaurants are within walking distance, too!

The Galleon, Key West
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.

1BR Condo Banyan Tree, KeyWest Unit 505/701
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.

1BR #405 Banyan Resort Key West, FL
Great location! Enjoyed the beauty of the banyan trees.
Resort rentals with a pool

Explore Key Largo! Beach Access, Pool, Parking!
The Key Largo location at Baker’s Cay is truly a gem! I would most definitely return in the future. There is so much to do and the resort is truly beautiful. I did not want to leave! The staff were also very friendly and helpful.

Pool, Private Beach Access, Pet-friendly!
It felt just like we booked through the actual hotel. The front desk even took my Hilton Honors membership and provided some upgrades. This was a great way to access such a beautiful resort at a reasonable rate and we’d certainly stay with them again.

Hyatt Beach House - Key West - Amazing Resort!!!
The condo was great! Nicely updated, close parking, view of the pool with easy access to the pool. Pool was large and never overly crowded. Nice little tiki bar near the pier. The beach wasn’t as big as it appeared in the pictures so that was a little disappointing but everything else was amazing! Met with the activities coordinator when we got there and he gave us the scoop on where to rent scooters, go snorkeling, and rent her skis. Overall, was a great experience!

Parrot's Perch
Our stay was perfect! This Airbnb was clean, spacious and exactly as described. The pull out sofa is a memory foam mattress - very comfortable. We love the location - close to everything but much quieter than being on Duval. The breakfast each morning was delicious. There are two pools and the smaller one was heated like a hot tub which was great during slightly cooler weather. You can’t go wrong with this stay. Highly recommend!

Hyatt Windward Pointe - Key West - Amazing Resort!
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.

Katie's Kottage
We had a wonderful! Everything was clean, perfect location and a private pool! Plus breakfast is included! Thanks so much Lisa!
Resort rentals with a gym

Explore Key Largo! Beach Access, Pool, Parking!
The Key Largo location at Baker’s Cay is truly a gem! I would most definitely return in the future. There is so much to do and the resort is truly beautiful. I did not want to leave! The staff were also very friendly and helpful.

Pool, Private Beach Access, Pet-friendly!
It felt just like we booked through the actual hotel. The front desk even took my Hilton Honors membership and provided some upgrades. This was a great way to access such a beautiful resort at a reasonable rate and we’d certainly stay with them again.

Ultimate Getaway! Private Beach Access, Pools
Beautiful resort! Would definitely stay here again. This was an adult trip but there was lots to do for kiddos too.

Keys Escape! Close to Beach Road, Onsite Pool!
We loved our stay at Bakers Cay. This is our 3rd time staying here, and booking with Victoria. The resort is beautiful. We loved being able to use kayaks and go fishing. We enjoyed restaurants in the area and a trip to the sandbar in Islamorada. We hope to come back again some time soon!

Studio - Hyatt Residence Club Key West
Great location and beautiful property! We’ll be back! Anthony was an excellent host!

The Galleon, Key West
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.
Quick stats about resort rentals in Key West
Total rentals
70 properties
Nightly prices starting at
£76 before taxes and fees
Total number of reviews
170 reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with a pool
70 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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