
Holiday rentals with a pool in Sunset Key
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Top-rated rentals with a pool in Sunset Key
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House rentals with a pool

Key West Charming by AvantStay | Week-Long Stays
Unbeatable location (in a quiet area walking distance from bars, restaurants, shops, museums, beaches, and parks!), and well kept condominium. Avantstay was very helpful and responded to my questions quickly. Loved the location so much! Would come back again

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!

106 Newly Renovated House with Oceanview and Pool
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.

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Gorgeous Romantic Private Villa, Steps from Duval!
We had a fantastic stay at Villa Serendipity. Great location right off Duval Street within walking distance to everything. Private and secluded. The pool is small and shared with 12 units, but it was nice. The courtyard is welcoming and peaceful. Bed was very comfortable. Well appointed kitchen; having the ice machine was great! Hosts communicate well. Parking was tight but once we got a spot we didn’t move the car for the rest of the trip. Overall had a great time at this excellent spot in Key West!

Waterfront Home 37.5-ft dock, Cabana Club Included
Clean house, well decorated, great location and responsive hosts! It’s also a plus that they accept pets for a reasonable pet fee. Key Colony Beach is a great location and this is a lovely little home. Book with confidence!

Paradise found
The house was clean and a great option for traveling as a large group. It was away from the bustle of Key West, but still easy to get around, and the restaurants nearby are delicious.

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
The house was exactly as pictured and in a very peaceful community. The beds were comfortable, as was the couch (two of our group opted to sleep on the couch itself instead of pulling out the sleeper sofa, and said it was pretty comfy!). Several of our group enjoyed using the bikes at night, and while we didn’t use the kayaks, it’s nice they were available. We didn’t get to do everything we hoped to do on our trip to Keys, but we plan to stay here again someday when we come back!
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.

Beach Heaven-Private Beach, Pool
Yuni was a great host! her place was just as described and we had a wonderful time.

EYW Getaway
We had a great stay! The place was clean, comfortable, and had everything we needed. The location was perfect, and communication with the host was smooth and easy. Would definitely stay here again, highly recommended!

Saltwater Harmony @ The Annex - Charming Condo
Had an incredible stay at Sweet Harmony! Super nice place with a great pool and the location was perfect. Everything was provided and the process was Super smooth. I was contacted throughout the process about every detail and Christian sent messages daily to check in or if I needed anything! Highly recommended......Would definitely stay here again! Thank you
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