Resort holiday rentals in Key West

Find and book unique resort rentals on Airbnb

0 of 0 items showing
1 of 3 pages

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 stars33 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 stars51 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 stars10 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
4.88 out of 5 average rating, 8 reviews

Hyatt Windward Pointe Resort: Beachfront Condo

LeighRating, 5 stars23 months ago
We really enjoyed our stay. The location is perfect, and there is a nice sidewalk along the water right across the street. There’s a nice pool, shuffle board, ping pong, and on site restaurant. Only took at most 10 to 15 minutes to everything in Key West. The rooms are perfect and offer privacy. Private bathroom for each room. Ample seating on the porch. A perfect area in the living room to play games. Im sure we will be back. :)
Resort in Key West
4.83 out of 5 average rating, 12 reviews

1BR Condo Banyan Tree, KeyWest Unit 505/701

JulieRating, 5 stars32 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 stars5 months ago
Great location! Enjoyed the beauty of the banyan trees.

Resort rentals with a pool

Resort in Key West
4.88 out of 5 average rating, 8 reviews

Hyatt Windward Pointe Resort: Beachfront Condo

LeighRating, 5 stars23 months ago
We really enjoyed our stay. The location is perfect, and there is a nice sidewalk along the water right across the street. There’s a nice pool, shuffle board, ping pong, and on site restaurant. Only took at most 10 to 15 minutes to everything in Key West. The rooms are perfect and offer privacy. Private bathroom for each room. Ample seating on the porch. A perfect area in the living room to play games. Im sure we will be back. :)
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
4.75 out of 5 average rating, 55 reviews

Charming 2 Bedroom Suite Beach Resort

NicoleRating, 5 stars3 months ago
Beautiful place! Very relaxing and peaceful. Also close to everything
Superhost
Resort in Key West

Enticing two Bedroom at Hyatt Sunset Harbor!

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

Studio - Hyatt Residence Club Key West

KatherineRating, 5 stars41 months ago
Great location and beautiful property! We’ll be back! Anthony was an excellent host!
Superhost
Resort in Key West
4.82 out of 5 average rating, 17 reviews

Katie's Kottage

SandyRating, 5 stars3 days 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!

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 stars13 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 stars41 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 stars10 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
4.88 out of 5 average rating, 8 reviews

Hyatt Windward Pointe Resort: Beachfront Condo

LeighRating, 5 stars23 months ago
We really enjoyed our stay. The location is perfect, and there is a nice sidewalk along the water right across the street. There’s a nice pool, shuffle board, ping pong, and on site restaurant. Only took at most 10 to 15 minutes to everything in Key West. The rooms are perfect and offer privacy. Private bathroom for each room. Ample seating on the porch. A perfect area in the living room to play games. Im sure we will be back. :)
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!

Quick stats about resort rentals in Key West

  • Total rentals

    70 properties

  • Nightly prices starting at

    ₹8,579 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