
Vacation rentals with a pool in Sunset Key
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Top-rated rentals with a pool in Sunset Key
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Popular amenities for Sunset Key rentals with a pool
House rentals with a pool

Gone Coastal
We enjoyed our stay here. It was an out a 20-25 minute drive to Duval so did have to take an Uber everywhere we went since we hadn’t rented a car. Overall it was a very nice place-we just weren’t crazy about the location.

Waterfront House - 30' Dock & Pool & Cabana Club
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!

Pelico Palms Sunset Suites
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!

Catherine House: A charming Old Town Key West
We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!

P23 - New 3 bedroom 2 bath duplex with private po
Our stay was wonderful! Key Colony is a quiet and peaceful community. Our condo was beautifully decorated and had everything we needed for the first couple days. The sheets and towels were soft The beds were very comfortable. We really enjoyed our stay and hope to go back soon again!

Casablanca ~ Fabulous Home w/ Private Pool/Parking
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.

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage
We had a great stay. The backyard is absolutely beautiful and feels very peaceful. We were treated to four manatees as well as a nurse shark off the dock over the course of our week here! The pool and spa were great and as advertised. Heather’s home is incredibly well stocked- more than enough towels for the baths and pool and the kitchen had everything needed for cooking as well as a great dishwasher which was great for vacation. Although we did have some issues with the property after check-in, the property host, Katie, was immediately available and very responsive to our concerns, and we were more than happy with the outcome. Would stay here again.

Sale! Pool, Hot Tub, Dock & Putting Green!
We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!
Condo rentals with a pool

2 Bedroom Oceanfront Complex Heated Pool KCB
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

On the water! Marina, Pool, Tiki Bar & Restaurant!
We loved our stay at the Dapper Dolphin! The space was so clean. Kate has everything there for you - from beach chairs to laundry detergent! This apartment is conveniently located to great restaurants, attractions and Sombrero Beach. You are just a short walk to the pool at Skipjack Resort. They have poolside karaoke on Monday nights which was very fun. Highly recommend booking this place - we miss it already!

Oceanfront 3 bed condo Ocean Edge w/ optional slip
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.

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants
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.

Top floor Ocean Views, Spacious 2 Bedroom Condo, V
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!!

Tropical Escape at Sunrise
Eric’s place was lovely, well maintained, nicely appointed, and immaculate. The 3 of us enjoyed the balcony overlooking the pool. Even though the apartment is near the airport we only heard planes twice in the 4 days we were there. There is a convenient little grocery store on the site and excellent BBQ from a food truck near the pool. Eric responded to our questions promptly. Comfy beds, everything worked and we enjoyed our stay. Would stay here again.

Anchor Drop modern elegance upgrades throughout vi
We loved everything about this place. It was super clean and fresh. The bedding was very comfortable and felt expensive. We drank coffee on the balcony every morning watching the ocean. The oceanfront pool area was clean and well taken care of. The unit was stocked and well labeled with all that we would need and more. The garage door opener for inside private parking was amazing. We watched the Tyson fight in the living room on the BIG tv! Had a great vacation. Thank you.

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"
Great Place! Everything was so easy from booking to checking out. Jennifer is very communicative, gives clear instructions and responds in a timely manner. The home is clean, comfy, has a very nice view, and we enjoyed sitting on the balcony and listening to the music from the restaurant down below (don't worry, the music stops at a reasonable hour). The downtown area is close enough for us to ride bikes. Publix grocery store is close by too. If we're ever back in Key West, we wouldn't hesitate to stay here again.
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