
Holiday rentals with a pool in Key West
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Top-rated rentals with a pool in Key West
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Popular amenities for Key West rentals with a pool
House rentals with a pool

Easy Livin' by AvantStay | Mins to the Ocean!
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!

Vaca Vista 3
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!!

Cudjoe Key Home with a View
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute
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.

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

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

Rise And Shine On The Water
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!

Truman's Trove at The Annex
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

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

Oceanfront 3 bed condo Ocean Edge w/ optional slip
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!

Galleon Resort - Walk to Duval & Mallory Square!
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.

Tropical Escape at Sunrise
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!

Affordable Beachfront Luxury Condo Sleeps 6
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.

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Kimberly’s condo was the perfect home base for exploring the upper keys. We enjoyed the views, the well equipped kitchen, and the pool!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
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!

Florida Keys Getaway - Slps 4 - Ocean View
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
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