
Vacation rentals with a pool in Big Pine Key
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Top-rated rentals with a pool in Big Pine Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Big Pine 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.

Islamorada Cay Home. Elegant home
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!

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!

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!

A Royal Escape in Key West
The Royal Escape house was beautiful inside and out. The outdoor patio & pool area was the perfect place to start the morning and end the day after a day out enjoying Key West. The house was spotless and had brand new appliances as well as plenty of supplies to get us through our stay. We loved the location -- the privacy was perfect and being just slightly off the main tourist areas of Key West was great. It was still an easy walk to everything, especially the beach. We will definitely come back for another visit.

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
Everything about this place was perfect! The location was great, plenty to do in the immediate area and close enough for a day trip to Key West. The pool and backyard provided everything we needed for those lazy days we just wanted to stay in and enjoy the Florida weather. Boat dock was really convenient for our boat rental. Fully functional kitchen and grill allowed us to prepare meals when we wanted. Our host was available anytime we had questions. Honestly don’t have one negative thing to say!
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!

BOOK today and enjoy our amazing discounts for yo
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.

Resort Condo: Pool | Marina | Beach | 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
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!

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.

Promenade to Paradise at The Annex
Absolutely fantastic unit and location, and the communication and service from Last Key was white glove. Top notch. We will be back.

Fully renovated 2/2 bath condo w/ shared pool!
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!
Quick stats about vacation rentals with a pool in Big Pine Key
Total rentals
130 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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