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Holiday rentals with a pool in Key West

Find and book unique homes with a pool on Airbnb

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Popular amenities for Key West rentals with a pool

House rentals with a pool

Superhost
Home in Key West
4.9 out of 5 average rating, 21 reviews

Easy Livin' by AvantStay | Mins to the Ocean!

KathleenRating, 5 stars3 weeks ago
The house was absolutely immaculate. We were so impressed with how clean everything was. My husband, who is an electrician, spotted an issue with the ceiling fans and when we reached out for assistance we got immediate attention from the friendliest employees. With it being in the perfect location you can walk to Duval St in minutes while still being in a quiet neighborhood. We had an unexpected guest, Charlie, the neighborhood cat who came outside the house to visit us. He was a pleasant surprise when we were missing our own furbabies at home! We are absolutely going to use AvantStay in the future!
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Vaca Vista 3

DoreenRating, 5 stars1 month ago
What a wonderful place to vacation. My entire family had a fabulous time. A bonus was seeing the manatees in the canal. The home was very clean and was very spacious. We all highly recommend this home!!
Guest favourite
Home in Cudjoe Key
4.97 out of 5 average rating, 159 reviews

Cudjoe Key Home with a View

RobRating, 5 stars3 weeks ago
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!
Superhost
Home in Key West
4.85 out of 5 average rating, 157 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

SarahRating, 5 stars1 month ago
Had a wonderful stay for 3 nights. The house was super clean and was located right behind the pool. The house had everything you could need for a stay in the Keys, including beach towels and chairs. Our only complaint was the upstairs AC struggled to keep up, with a noticeable difference between the upstairs and downstairs. However, there were plenty of fans for us to use making this less of an inconvenience as it would have been. Overall would recommend this property for anyone who wants to stay close to Key West but far enough to have peace and quiet.
Superhost
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars2 weeks ago
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 265 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

FrankRating, 5 stars1 day ago
We had a great time at Janet and Jerry’s home at Venture Out in Cudjoe Key! We made the short drive down to Key West after some morning pickleball. Our only unexpected (not welcome) surprise was the rotten egg smell all the way down the Keys. The smell is apparently from the over abundant seaweed blooming due to very warm water temps. Unfortunately this is a norm between May and October now? Key West did not have the smell due to wind direction, so overall we really enjoyed our stay!
Guest favourite
Home in Cudjoe Key
4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

FlorianRating, 5 stars1 month ago
There were five of us in the house and we immediately felt comfortable. Everything was super clean. The location directly on the water was overwhelming as expected. Everything that is needed was there. The kitchen and terrace were very large and the mattresses were very comfortable. Key West is about 30 minutes away. Check-in and check-out as well as contact were completely unproblematic. We will be back!
Luxe
Home in Key West
4.83 out of 5 average rating, 6 reviews

Truman's Trove at The Annex

KristaRating, 5 stars2 months ago
Wonderful location, quiet community, and the property manager was amazing with communication. The home was absolutely beautiful, a great outdoor space, clean and cozy. Definitely would recommend!!

Apartment rentals with a pool

Superhost
Apartment in Key West
4.83 out of 5 average rating, 276 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

MichaelRating, 5 stars3 weeks ago
Right next to Duval Street, easily walkable to major attractions, restaurants, bars.. Host was super responsive, friendly, and really worked with us on anything we needed.. Great place!
Guest favourite
Apartment in Key West
4.97 out of 5 average rating, 74 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

BrianRating, 5 stars2 months ago
Great space with everything you need. Patio is a perfect place to relax. The house is well stocked. Plenty of room for a group. Access to hotel pools/restaurant with transportation into town if you need it. Great host communication. All you could want!
Superhost
Apartment in Key West
5 out of 5 average rating, 6 reviews

Galleon Resort - Walk to Duval & Mallory Square!

PatriciaRating, 5 stars5 months ago
Incredible view! Place was clean and what we expected. Gorgeous unit right on the water. Watching the boats go by was so relaxing. Tiki bar right below us was convenient if we wanted a drink while relaxing. Had a small problem with the dryer and they came to fix it within the hour, so I was more than satisfied with upkeep. Walk to restaurants and hot spots was easy. Great Irish pub a block away (Celtic Conch). Unit is convenient for any type of boating excursion you would like to book as the boardwalk/marina is right there. Chris, our host, was very responsive to any questions we had and very helpful in booking arrangements. We did not have recommendation questions for him, as we’ve been to key west a number of times and have friends who live there, but I’m sure based on the dealings we had with him, he’d be happy to help. One note, this is a timeshare community. I was worried we’d be hounded. We were not.
Guest favourite
Apartment in Key West
4.89 out of 5 average rating, 142 reviews

Tropical Escape at Sunrise

MalloryRating, 5 stars4 weeks ago
We enjoyed our stay! A little outside of the heart of Key West so it was very quiet. This place does have a unit above, luckily we were not bothered by any sort of upstairs noise. Would recommend!
Guest favourite
Apartment in Key West
4.78 out of 5 average rating, 299 reviews

Affordable Beachfront Luxury Condo Sleeps 6

SharonRating, 5 stars1 month ago
Traci’s condo was great in every way! Everything was very clean and the view was amazing. We could enjoy watching the turquoise water and swaying palm trees from almost every room – both bedrooms, living room, kitchen, dining area, or relaxing on the large balcony. Some of the furniture is different in the photos, but my group agrees it is even better now than what you see. Having our own parking space in the garage was much appreciated, too. Traci responded quickly; clear check-in instructions. We would definitely stay here again.
Guest favourite
Apartment in Tavernier
4.9 out of 5 average rating, 288 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

MariaRating, 5 stars2 weeks ago
Kimberly’s condo was the perfect home base for exploring the upper keys. We enjoyed the views, the well equipped kitchen, and the pool!
Guest favourite
Apartment in Tavernier
4.94 out of 5 average rating, 146 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

KatieRating, 5 stars3 weeks ago
This is a top notch airbnb. Excellent communication from the host, extremely clean, well stocked condo, generous supplies beautiful decor. We stayed 8 days in the condo and felt right at home. Loved the large pool. We caught many fish and cooked at the condo all but 2 evenings and had everything we needed to prepare meals. Really appreciated the assortment of coolers provided for day trips. Thank you again, John!
Superhost
Apartment in Tavernier
4.77 out of 5 average rating, 369 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Angel MiguelRating, 5 stars3 weeks ago
Would come back again. Very peaceful and good location. Host was very responsive and friendly.

Quick stats about holiday rentals with a pool in Key West

  • Total rentals

    1.7K properties

  • Nightly prices starting at

    ₹6,923 before taxes and fees

  • Total number of reviews

    40K reviews

  • Family-friendly rentals

    1.1K properties are a good fit for families

  • Pet-friendly rentals

    520 properties allow pets

  • Rentals with dedicated workspaces

    900 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Rentals with pools