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

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.

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!

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

Ultimate Getaway! Private Beach Access, Pools
This resort was absolutely stunning, and we will definitely be visiting again! The beaches and pool were perfect and the Bakers Cay staff was unbelievably friendly and helpful throughout our entire trip. Both restaurants on site were also delicious and very conscientious of any allergies. I will say that since this particular Airbnb host is actually a third-party company, the communication was a little bit poor (they could not provide me with a confirmation number); however everything worked out great and the hotel had our room ready for us.

Charming 2 Bedroom Suite Beach Resort
We were amazed by this property. pics weren't exactly like the unit we got, but very comparable. it was the first floor in the building closest to the beach. It was steps to the pool, the ocean and a bar Rita at the front desk was very helpful. p.s. the beds were very comfortable

Enticing two Bedroom at Hyatt Sunset Harbor!
Concierge was AMAZING to work with, so helpful and kind.

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!

Katie's Kottage
Very convenient. Rained a lot so didn’t get to use pools as much but liked the layout. Breakfast was a nice touch and lived the refreshed linens and towels daily. Only small suggestion is a small table in lower level bedroom.

Orchid Suite
Loved the place and the location. Peaceful and quiet on a beautiful street in Old Town, but walking distance to restaurants and bars. Communication was great, too. Would definitely stay here again!

Fleming's Veranda Townhome

Relaxing Ocean Front Suite w/ Outdoor Pool
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.

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

Pool, Private Beach Access, Pet-friendly!
The friendly and attentive staff really made our stay top tier. This is a beautiful place to relax and have fun.

Ultimate Getaway! Private Beach Access, Pools
This resort was absolutely stunning, and we will definitely be visiting again! The beaches and pool were perfect and the Bakers Cay staff was unbelievably friendly and helpful throughout our entire trip. Both restaurants on site were also delicious and very conscientious of any allergies. I will say that since this particular Airbnb host is actually a third-party company, the communication was a little bit poor (they could not provide me with a confirmation number); however everything worked out great and the hotel had our room ready for us.

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!

Windward Point Beachfront Resort, Hot Tub, Pool

Studio Galleon, Hot Tub, In Town, Pool, Marina
Quick stats about resort rentals in Key West
Total rentals
70 properties
Nightly prices starting at
$166 NZD 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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