Holiday rentals with a pool in Big Pine Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Big Pine Key rentals with a pool

House rentals with a pool

Top Guest favourite
Home in Marathon
4.99 out of 5 average rating, 138 reviews

Cancellation Deal: 08/02 thru 08/09

ShelleyRating, 5 stars1 week ago
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!
Guest favourite
Home in Marathon
5 out of 5 average rating, 14 reviews

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024

AieshaRating, 5 stars1 week ago
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.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Key West
4.92 out of 5 average rating, 290 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

LoriRating, 5 starstoday
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!
Superhost
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars3 weeks ago
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!
Superhost
Home in Summerland Key
5 out of 5 average rating, 3 reviews

Waterfront Beach House with Dock & Heated Pool!

HeatherRating, 5 stars1 month ago
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.
Guest favourite
Home in Cudjoe Key
4.95 out of 5 average rating, 22 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

AlysonRating, 5 stars4 weeks ago
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

Guest favourite
Condo in Key West
4.95 out of 5 average rating, 39 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Lori Rating, 5 stars1 month ago
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.
Guest favourite
Condo in Key West
4.9 out of 5 average rating, 143 reviews

Tropical Escape at Sunrise

CameronRating, 5 stars3 weeks ago
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.
Guest favourite
Condo in Key West
4.89 out of 5 average rating, 168 reviews

A Perfect Getaway

DavidRating, 5 stars3 weeks ago
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.
Guest favourite
Condo in Key West
4.95 out of 5 average rating, 152 reviews

Fully renovated 2/2 bath condo w/ shared pool!

TinaRating, 5 stars1 week ago
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.
Guest favourite
Condo in Key West
4.9 out of 5 average rating, 211 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

AlexRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 20 reviews

*NEW* Private Beach, pool & fully loaded kitchen

JamesRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 14 reviews

Ocean Potion 1B/2B 3Balconies Ocean View

SueRating, 5 stars1 month ago
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!
Superhost
Condo in Marathon
4.85 out of 5 average rating, 239 reviews

Sombrero Beach Tropical Getaway

JoseRating, 5 stars1 day ago
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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