Holiday rentals with a pool in Sunset Key

Sharon was an excellent host that answered any of our questions promptly. The place was even better than what the photos showed. Comfortable enough for 7 people to stay for a long weekend. We didn't use the pool, but it was nice to have the option. Easy to get into the gated community, and we didn't struggle to find parking with our rental car. Easy to get to many different popular spots around Key West with rideshare. Convenient to have some convenience stores like CVS within walking distance, and a Publix not too far via car. Only thing I would improve is having more toilet paper and hand soap refills in each bathroom, especially with 7 people staying over a long weekend.

We loved our stay and will definitely recommend to friends and family. Hope to return someday soon!

Beautiful place to stay with family and friends. The location is great. Everything was as described in the listing. We really enjoyed our time there.

This was an awesome home for our family of 4 + dog. We felt right at home for the week! The pool was perfectly warm, and the kids had so much fun playing by the dock. We rented a pontoon boat and were able to dock it easily. Honestly, we hardly used the other amenities in the home because the weather was so nice, but if it rained we probably would have loved the game room too! Overall this was a great home for our family. The neighborhood isn’t super walkable, but the grocery store was just down a little footpath, allowing us to walk to get groceries as needed. Loved this!

We did a couples’ trip with our three toddlers and had a wonderful stay at Ruth’s place! We had everything we needed and the location was awesome - close to beautiful Sombrero beach, restaurants, nightlife and had a dock where we could dock our rental boat. Would come back in a heartbeat!

fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!

We recently had the pleasure of staying at a fantastic vacation rental, and it exceeded all our expectations! The house was comfortable, spacious, and perfectly equipped for a peaceful and relaxing stay. One of the highlights was the location—just a short and scenic walk to the beach, making it easy to enjoy the sound of the waves and the coastal vibe. We were also treated to the most beautiful sunrises each morning, a sight that truly made the experience unforgettable. The home was spotlessly clean, with thoughtful details that made us feel at ease. And Sheri, the host, was incredibly friendly and welcoming, ensuring every part of our stay was smooth and enjoyable. Her kindness added an individualized touch to the experience. If you’re looking for a perfect getaway with stunning views, a cozy atmosphere, and a host who genuinely cares, this place is absolutely worth considering!

The house is perfect! It’s very clean and has everything you need. The kitchen is fully stocked with plates, glasses, etc. The bathroom had a nice shower and plenty of towels. We love the location! We parked our car and never used it. You can walk everywhere. The backyard is amazing. The pool is beautiful. We swam every day and loved sitting in the yard relaxing. We will be back.

Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

Absolutely amazing! Our stay at Key West Hideaways exceeded every expectation. The location couldn't have been better—just steps away from Duval Street, yet blissfully quiet, offering the perfect balance of excitement and relaxation. The property itself was even better than the photos, which is a rare treat. Everything was within walking distance, making it incredibly convenient to explore all that Key West has to offer. The cleanliness was impeccable. The housekeeping and maintenance team deserve major kudos for keeping the grounds and common areas spotless. We were blown away by the attention to detail—you didn’t even see handprints on the stainless steel elevator for the entire week we were there! That level of care is hard to find. This was hands down the best Airbnb experience we’ve ever had, and we can’t imagine staying anywhere else when we visit Key West in the future. Highly recommended to anyone looking for a perfect getaway!

Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!

We enjoyed our stay in Key West away from the hub-bub of Duvall Street! We had a rental car for getting around the island. The condo was great for our group of 4. Two full bathrooms were a bonus! Very clean! Smathers Beach was a short drive away. Free parking for a public beach with bath house! Also super close to the airport, but we never heard any overnight flights. A great spot!

We had a great stay at Chris’s place in Key West! The property was exactly what we needed for a relaxing getaway. Chris is an excellent communicator—his instructions were clear, detailed, and made everything super easy from check-in to check-out. We felt well taken care of and really appreciated the smooth experience. I’d definitely recommend this place to anyone planning a trip to Key West!

Went for a quick fishing trip. Great location. Enjoyed it so much

Mike was great and communicative the whole time leading up to the stay. The place was great. I would totally stay again.