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Vacation rentals with a pool in Sugarloaf Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Sugarloaf Key rentals with a pool

House rentals with a pool

Guest favorite
Home in Key West
4.9 out of 5 average rating, 70 reviews

Casa Loca

ElizabethRating, 5 stars2 months ago
Casa loca was Absolutely beautiful! So close to everything in the keys. Host super friendly and helpful. The house was very clean! 10/10 stay LOVED IT!
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars18 months ago
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
Guest favorite
Home in Key Largo
4.94 out of 5 average rating, 68 reviews

Casa Solaris | Key Largo home with Private Pool!

JeffRating, 5 stars4 days ago
I am typically not an Airbnb person, as I prefer a hotel. This home was better than any resort we could’ve stayed at. Check in was simple. The home was beautiful. The location was perfect. Our favorite part was the second space that was separate from the main house. We are a family of four (mom, dad and two kids) who were traveling with my sister. She was able to have her own space with a private bathroom and entrance and could “go home” when the craziness of two kids was enough. Both units were adequately stocked with towels and linens. The kitchens had anything you could need including coffee maker, blender, toaster, pots and pans. The pool and hot tub were incredible! So much so, that we took two full days and only left for dinner! Sean and Denise were great hosts and super responsive! We will be back.
Superhost
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars1 week ago
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!
Top guest favorite
Home in Key West
5 out of 5 average rating, 7 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

AmyRating, 5 stars1 week ago
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.
Guest favorite
Home in Key Colony Beach
4.97 out of 5 average rating, 36 reviews

P23 - New 3 bedroom 2 bath duplex with private po

AndreaRating, 5 stars13 months ago
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!
Guest favorite
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars3 days ago
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!
Superhost
Home in Marathon
4.73 out of 5 average rating, 60 reviews

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage

MichelleRating, 5 stars2 weeks ago
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.

Condo rentals with a pool

Superhost
Condo in Key Colony Beach
4.75 out of 5 average rating, 164 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

RobertRating, 5 stars4 weeks ago
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!
Superhost
Condo in Key West
4.68 out of 5 average rating, 85 reviews

BOOK today and enjoy our amazing discounts for yo

MarkRating, 5 stars1 month ago
We had a great time at Julia's place! The condo was beautifully furnished and we enjoyed pool and private beach area. We love to walk and the location was perfect for us! The nearby deli and restaurants were also very good. Ubers are very quick and reasonable.
Guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 18 reviews

Resort Condo: Pool | Beach | Marina | Pickleball

SamRating, 5 stars1 week ago
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!
Guest favorite
Condo in Key West
4.97 out of 5 average rating, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in Tavernier
4.89 out of 5 average rating, 133 reviews

1BR - Key Largo Sun & Sand Hideaway

JosephRating, 5 stars1 week ago
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.
Superhost
Condo in Key West
4.73 out of 5 average rating, 94 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

JudyRating, 5 stars1 month ago
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!!
Guest favorite
Condo in Key West
4.9 out of 5 average rating, 138 reviews

Tropical Escape at Sunrise

RobertaRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in Tavernier
4.9 out of 5 average rating, 280 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

KristenRating, 5 stars1 week ago
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 !!!!

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