Resort holiday rentals in Key West

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Popular amenities for resort rentals in Key West

Family-friendly resort rentals

Resort in Key West
4.67 out of 5 average rating, 9 reviews

Studio#202CondoBanyan Tree Key West

MelissaRating, 5 stars31 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.
Superhost
Hotel room in Key Largo
4.67 out of 5 average rating, 6 reviews

Key Largo Cottages w/ Free Sailboat, Kayaks + More

NataliaRating, 5 stars49 months ago
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!
Resort in Key West
5 out of 5 average rating, 5 reviews

The Galleon, Key West

KimmyRating, 5 stars8 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
4.83 out of 5 average rating, 12 reviews

1BR Condo Banyan Tree, KeyWest Unit 505/701

JulieRating, 5 stars30 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
4.88 out of 5 average rating, 16 reviews

1BR #405 Banyan Resort Key West, FL

KimRating, 5 stars3 months ago
Great location! Enjoyed the beauty of the banyan trees.

Resort rentals with a pool

Hotel room in Key Largo
4.83 out of 5 average rating, 12 reviews

Explore Key Largo! Beach Access, Pool, Parking!

BethanyRating, 5 stars12 months ago
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.
Hotel room in Key Largo
4.8 out of 5 average rating, 10 reviews

Pool, Private Beach Access, Pet-friendly!

TerryRating, 5 stars21 months ago
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.
Resort in Key West
4.75 out of 5 average rating, 4 reviews

Hyatt Beach House - Key West - Amazing Resort!!!

StacyRating, 5 stars45 months ago
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!
Superhost
Resort in Key West
4.91 out of 5 average rating, 11 reviews

Parrot's Perch

Bernard And TracyRating, 5 stars1 month ago
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!
Resort in Key West
5 out of 5 average rating, 4 reviews

Hyatt Windward Pointe - Key West - Amazing Resort!

DonnaRating, 5 stars36 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, 15 reviews

Katie's Kottage

BreannaRating, 5 stars1 month ago
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

Hotel room in Key Largo
4.83 out of 5 average rating, 12 reviews

Explore Key Largo! Beach Access, Pool, Parking!

BethanyRating, 5 stars12 months ago
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.
Hotel room in Key Largo
4.8 out of 5 average rating, 10 reviews

Pool, Private Beach Access, Pet-friendly!

TerryRating, 5 stars21 months ago
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.
Guest favourite
Hotel room in Key Largo
4.87 out of 5 average rating, 89 reviews

Ultimate Getaway! Private Beach Access, Pools

MackenzieRating, 5 stars2 months ago
Beautiful resort! Would definitely stay here again. This was an adult trip but there was lots to do for kiddos too.
Hotel room in Key Largo
4.82 out of 5 average rating, 50 reviews

Keys Escape! Close to Beach Road, Onsite Pool!

StacyRating, 5 stars1 month ago
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!
Resort in Key West
4.67 out of 5 average rating, 3 reviews

Studio - Hyatt Residence Club Key West

KatherineRating, 5 stars39 months ago
Great location and beautiful property! We’ll be back! Anthony was an excellent host!
Resort in Key West
5 out of 5 average rating, 5 reviews

The Galleon, Key West

KimmyRating, 5 stars8 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.

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Resort rentals