
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

The Toasted Coconut-Pool-Bikes-Grill-Chic!
Thank you, dear hosts, for the best vaca I've had in years! We loved everything about the house. Plenty of room to spread out and stocked with kitchen accessories, linens, towels, toiletries, etc. The children spent a lot of time in the pool. The adults could relax in the multiple patio chairs, grill our food, all while watching them splash to their heart's content! The Keys were amazing and unique. I didn’t realize how fun snorkeling can be! Sincerely, Rita Dorsey and Family

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.

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.

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!

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Possibly the best Airbnb I have ever stayed at, all amenities listed are better than expected. Host and staff were amazing. Could not get a better location in Key West. We were even going to change plans and stay an extra day, but just couldn’t make it work with the timing of our travel. 6 stars😁 Clean, quiet, perfect!

Spacious lux home, private pool/spa, 80' dock
Beautiful, roomy, comfortable, well appointed home. Has absolutely everything you could need for an incredible vacation! Great little gym, really nice bikes, coolers, pool floats, beach umbrellas, kayaks and paddle boards. The entire game room area is such a great place to hang out. Good size pool, shade keeps it nice and cool. Quiet neighborhood. Owners are super responsive, very helpful. We really loved this place!

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.
Condo rentals with a pool

La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Right next to Duval Street, easily walkable to major attractions, restaurants, bars.. Host was super responsive, friendly, and really worked with us on anything we needed.. Great place!

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.

*NEW* Kokomo Views-Pool/Beach
Our stay was wonderful. The condo was spotless and had everything we needed and more. The beds were comfy. The views were amazing. Would stay there again

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.
Quick stats about vacation rentals with a pool in Big Pine Key
Total rentals
130 properties
Nightly prices starting at
ﺩ.ﺇ404 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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