Resort vacation rentals in Key West

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Popular amenities for Key West resort rentals

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 stars10 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 stars20 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
4.83 out of 5 average rating, 12 reviews

1BR Condo Banyan Tree, KeyWest Unit 505/701

JulieRating, 5 stars29 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.
Superhost
Resort in Key West
4.91 out of 5 average rating, 11 reviews

Parrot's Perch

Bernard And TracyRating, 5 stars2 weeks 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 stars35 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
4.83 out of 5 average rating, 12 reviews

Katie's Kottage

JennRating, 5 stars4 weeks ago
Great place to stay. Close to everything! The property is quiet and relaxing and the pool was great!

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 stars10 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.
Resort in Key West
5 out of 5 average rating, 5 reviews

The Galleon, Key West

KimmyRating, 5 stars7 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.
Hotel room in Key Largo
4.8 out of 5 average rating, 10 reviews

Pool, Private Beach Access, Pet-friendly!

TerryRating, 5 stars20 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.
Top guest favorite
Hotel room in Key Largo
4.88 out of 5 average rating, 88 reviews

Ultimate Getaway! Private Beach Access, Pools

MackenzieRating, 5 stars1 month 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 stars2 weeks 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!

Quick stats about resort rentals in Key West

  • Total rentals

    50 properties

  • Nightly prices starting at

    $100 before taxes and fees

  • Total number of reviews

    160 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

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