Resort holiday rentals in Key West

Find and book unique resort stays on Airbnb

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Popular amenities for Key West resort stays

Resort rentals with a pool

Guest favourite
Hotel room in Key Largo
4.87 out of 5 average rating, 95 reviews

Ultimate Getaway! Private Beach Access, Pools

LukeRating, 5 stars3 weeks ago
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.
Resort in Key West
4.72 out of 5 average rating, 58 reviews

Charming 2 Bedroom Suite Beach Resort

RoseRating, 5 stars2 weeks ago
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
Superhost
Resort in Key West

Enticing two Bedroom at Hyatt Sunset Harbor!

SheilaRating, 5 stars2 months ago
Concierge was AMAZING to work with, so helpful and kind.
Superhost
Resort in Key West
4.91 out of 5 average rating, 11 reviews

Parrot's Perch

Bernard And TracyRating, 5 stars3 months 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!
Superhost
Resort in Key West
4.82 out of 5 average rating, 17 reviews

Katie's Kottage

SandyRating, 5 stars1 week ago
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.
Superhost
Resort in Key West

Orchid Suite

AnthonyRating, 5 stars3 months ago
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!
Superhost
Resort in Key West

Fleming's Veranda Townhome

Superhost
Hotel room in Islamorada

Relaxing Ocean Front Suite w/ Outdoor Pool

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 stars14 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
4.67 out of 5 average rating, 3 reviews

Studio - Hyatt Residence Club Key West

KatherineRating, 5 stars42 months ago
Great location and beautiful property! We’ll be back! Anthony was an excellent host!
Hotel room in Key Largo
4.82 out of 5 average rating, 11 reviews

Pool, Private Beach Access, Pet-friendly!

JanaRating, 5 stars1 month ago
The friendly and attentive staff really made our stay top tier. This is a beautiful place to relax and have fun.
Guest favourite
Hotel room in Key Largo
4.87 out of 5 average rating, 95 reviews

Ultimate Getaway! Private Beach Access, Pools

LukeRating, 5 stars3 weeks ago
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.
Hotel room in Key Largo
4.82 out of 5 average rating, 50 reviews

Keys Escape! Close to Beach Road, Onsite Pool!

StacyRating, 5 stars3 months 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!
Superhost
Resort in Key West

Windward Point Beachfront Resort, Hot Tub, Pool

Superhost
Resort in Key West

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

Destinations to explore

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