
Vacation rentals with a pool in Sugarloaf Key
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Top-rated rentals with a pool in Sugarloaf Key
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Popular amenities for Sugarloaf 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.

Coastal Comfort; Waterfront Luxury Home with priva
We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service

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!

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
We had a great time at Judy’s airbnb. It was super nice, clean and had really comfortable beds. The pool was right across the parking area, very clean, private and always had chairs available. Over all our stay was great and we will definitely be back.

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!

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!

Islamorada Reef Canal & Pool home off Tav Creek-
Isa was an amazing host! The house is beautiful and pristine! We loved the pool and how close the house is to everything. Our only regret is we couldn’t stay longer!!!! Thank you so much!
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!

Resort Condo: Pool | Beach | Marina | Pickleball
This place was great for an in between Miami and Key West! The pool was perfect for relaxing at all day! Restaurants near by were all fantastic! Doable drives for day trips to key west and Miami!

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.

1BR - Key Largo Sun & Sand Hideaway
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.

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.

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
My twin sister and I had such a wonderful time at Kim's home celebrating our birthday. She is super responsive and the place was exactly as described! It was so nice to sit on the patio in the morning and overlook the beautiful water. Pool is very nice and plenty to do in the property with the beach, tennis courts, BBQ, restaurant/baror just walk around in a safe, secluded environment. Condo was perfectly appointed with all the comforta and amenities of home! Can't wait to visit with Kim again! Wish I could give her 10 stars !!!!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again
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