Resort vacation rentals in Key West

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Popular amenities for Key West resort rentals

Resort rentals with a pool

Resort in Key West

4.83 out of 5 average rating, 12 reviews

1BR 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 reviews

Charming 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 reviews

1BR #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 reviews

Parrot'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 reviews

Hyatt 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 reviews

Katie'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!

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

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