
Holiday rentals with a pool in Big Pine Key
Find and book unique homes with a pool on Airbnb
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

Cancellation Deal: 08/02 thru 08/09
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024
We loved the house! Everything was exactly as described. I would even say pictures didnt do complete justoce to the space and views! We had everything we needed at the house with ample dishes and cookware. We drove down to Key West which wasnt too far of a trip. We definitely would always recommend and stay again! Jessieca was an amazing host with great recommendations and general info for the area.

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Family House, 2 K BR's, Private Spa/Deck, 2 pools.
Fabulous vacation in Key West with family. Location was convenient, quiet, and beautiful. Although only a block from Duval, the space was far from chaotic. Beautiful pool and surrounding area. The house could not have been more clean, and instructions were extremely easy to follow. Would recommend this space to all!

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

Waterfront Beach House with Dock & Heated Pool!
House was very clean, host very responsive, beautiful location, pool was perfect and the view was amazing. Definitely recommend and will be staying there again.

Oceanside home 107,dock,kayaks,bikes,pool,fishing,
loved staying here - amenities were so awesome our teens loved fishing off the dock and learned to kayak with the provided equipment. comfy beds and plenty of extras that were thought of for guests. the area feels very private. highly recommended!
Condo rentals with a pool

Condo de Paradise/Salt Water Pool/Boat Dock
We are absolutely in love with this place. The views are gorgeous. the grounds were immaculately groomed. There are so many colorful trees and flowers. The pool is slightly heated, which is perfect. Everyone we met was so nice and helpful with recommendations. We got to see the jets fly over a few times, so cool. The kitchen has everything you need to prepare meals and snacks. The beds in both rooms are very comfortable. We hope to stay here again in the future.

Tropical Escape at Sunrise
Great place to stay. Overall very satisfied. Nice patio area. Clean condo. Having accommodations there in place was a nice touch as well. Would recommend staying here for your trip to Key West.

A Perfect Getaway
We had a wonderful visit in Key west. The place was very clean, close to everything. We enjoyed this place very much and would rent it again. Thank you so very much. Sue and Dave Hopper.

Fully renovated 2/2 bath condo w/ shared pool!
This listing was everything and more! The space was very clean, and provided all of the necessary amenities. As far as location…top tier. All the major attractions and beaches were a short 15 minute drive. Chris was responsive when I reached out. Truly a gem, and I would recommend this space again and again.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
Jennifer’s place was exactly what we were looking for, it was a quiet corner unit with lots of space for four guests, a large kitchen (we love to cook elaborate meals even when we travel and we had everything we needed here), great views of the harbor, was squeaky clean, and ample parking. Jennifer communicated everything we needed to know well ahead of time and promptly replied to any questions we had. Would absolutely stay here again!

*NEW* Private Beach, pool & fully loaded kitchen
Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.

Ocean Potion 1B/2B 3Balconies Ocean View
The place was very comfortable, very well appointed and centrally located to all kinds of great things to do! The one issue we reported was addressed right away! Would definitely go back!

Sombrero Beach Tropical Getaway
The room was very clean and tidy and perfectly cooled temperature. All amenities worked and were very clean. Enjoyed the security of the place. We enjoyed the stay & will book again for later trips to the area. Very recommended! Thanks Phil!
Quick stats about holiday rentals with a pool in Big Pine Key
Total rentals
130 properties
Nightly prices starting at
$184 NZD 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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