Holiday rentals with a pool in Key Haven, Key West

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Popular amenities for Key Haven, Key West rentals with a pool

House rentals with a pool

Guest favourite
Home in Key West
4.97 out of 5 average rating, 38 reviews

Casa Serendipity at Old Town

PamelaRating, 5 stars1 week ago
Highly recommend this place for a top notch experience with a home that matched and exceeded our expectations for a Key West experience. The service was impeccable and went out of their way to make us comfortable and feel welcome.
Top Guest favourite
Home in Marathon
4.99 out of 5 average rating, 138 reviews

Cancellation Deal: 08/02 thru 08/09

ShelleyRating, 5 stars1 week ago
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!
Guest favourite
Home in Marathon
5 out of 5 average rating, 14 reviews

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024

AieshaRating, 5 stars1 week ago
We loved the house! Everything was exactly as described. I would even say pictures didnt do complete justoce to the space and views! We had everything we needed at the house with ample dishes and cookware. We drove down to Key West which wasnt too far of a trip. We definitely would always recommend and stay again! Jessieca was an amazing host with great recommendations and general info for the area.
Guest favourite
Home in Cudjoe Key
4.97 out of 5 average rating, 160 reviews

Cudjoe Key Home with a View

YirenyRating, 5 stars2 weeks ago
The house is located in a peaceful community with a store inside that was perfect because you don’t have to drive to get basic necessities. Pool and spa were perfect. And the view is magical. The house was cleaned and beautifully decorated. The outside areas were perfect too. I loved take breakfast on the porch.
Guest favourite
Home in Cudjoe Key
4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

JoanRating, 5 stars1 month ago
As always, Michael’s place was spotless, perfectly stocked and just as pictured. We come back here annually to fish at Sugarloaf Marina and are always satisfied. Michaels house is in the perfect location, with the best sunsets, an amazing dock and pool, and the house is always stocked and we're able to relax for another day of tarpon fishing.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Grand Blue Arenas/ 120'Dock/Mini golf/GameRoom

GinaRating, 5 stars1 week ago
We had an absolutely amazing stay at this beautiful home in Marathon Keys! From the moment we arrived, it was clear that this property is extremely well-maintained and spotless. The house was immaculately clean, which made settling in with kids feel effortless and comfortable.The two-story layout was perfect for our family, offering plenty of space for everyone to spread out and relax. The home is definitely kid-friendly and family-oriented, with thoughtful touches throughout. The pool was a huge hit with both the kids and adults, and we had so much fun spending our evenings enjoying it! The kitchen was gorgeous and fully equipped with high-quality appliances, which made cooking meals together easy and enjoyable. We brought both a 22-foot bay boat and a 22-foot pontoon, and docking was a breeze. Overall, this home was the perfect place for our family getaway. We made unforgettable memories here and would absolutely return. Highly recommended for families looking for a home in the Keys!
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 stars3 days 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, 35 reviews

Rise And Shine On The Water

JemmaRating, 5 starstoday
The home is beautiful and not too far from Key West. Very calm peaceful area, and we loved the view.

Condo rentals with a pool

Superhost
Condo 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 stars4 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!
Superhost
Condo 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.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 14 reviews

*NEW* Kokomo Views-Pool/Beach

CourtneyRating, 5 stars4 weeks ago
The condo was spacious, super clean and absolutely beautiful! Steps from the beach and pool. Broken shelf in the master shower made for a minor inconvenience but we understand things happen. Would stay again!
Superhost
Condo in Key West
4.86 out of 5 average rating, 14 reviews

Andy’s Attic | Budget-Friendly!

ChristinaRating, 5 stars3 weeks ago
The room was very small, but was exactly as described. It required a bit of creativity to unpack, but once we figured out how to set ourselves up it was perfect. Perfect location and accommodations. Staff was super responsive & helpful with our random questions. Definitely encourage visitors to rent bicycles to get around!
Guest favourite
Condo 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.
Superhost
Condo in Key West
4.89 out of 5 average rating, 27 reviews

New Listing! Key Lime Paradise/Condo

StevenRating, 5 stars1 week ago
We Definitely would stay again if we are in the area. The place was exactly as advertised and centrally located. we had a nice relaxing time.
Top Guest favourite
Condo in Key West
5 out of 5 average rating, 33 reviews

EYW Getaway

JaneRating, 5 stars1 week ago
We were next to the airport but didn't hear the planes. It was far away from Key West tourist attractions and restaurants. It was nice to come back to our place for peace and quiet. It was nicely decorated and felt like a beach get-away.
Top Guest favourite
Condo in Marathon
4.96 out of 5 average rating, 103 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars3 weeks ago
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.

Quick stats about holiday rentals with a pool in Key Haven, Key West

  • Total rentals

    70 properties

  • Nightly prices starting at

    $151 NZD before taxes and fees

  • Total number of reviews

    990 reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

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