Vacation rentals with a pool in Big Pine Key

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Popular amenities for Big Pine Key rentals with a pool

House rentals with a pool

Top guest favorite
An outdoor Tiki bar area with tall bar stools arranged around a counter. The bar features a sign reading 'Toasted Coconut Tiki Bar'. A serene sunset sky illuminates the scene, while palm trees and a fenced space add to the tropical ambiance.
Home in Marathon
5 out of 5 average rating, 51 reviews

The Toasted Coconut-Pool-Bikes-Grill-Chic!

RitaRating, 5 stars2 weeks ago
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
Top guest favorite
An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.
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 favorite
The image showcases a modern two-story home with a light blue exterior, surrounded by lush landscaping. A heated pool is visible in the foreground, alongside kayaks and paddle boards. The ocean view offers clear, open water, enhancing the tranquil setting of 'The 7-Mile Villa.'
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.
Top guest favorite
An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.
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.
Superhost
A serene outdoor space includes a private pool surrounded by a spacious deck. Palm trees frame the scene, casting shadows on the white tiles. A furnished sitting area can be seen nearby, offering a relaxing spot to enjoy the warm weather.
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!
Top guest favorite
A swimming pool area is surrounded by tropical landscaping, featuring lounge chairs positioned for relaxation. The white cottage with a sloping roof is visible in the background, complemented by vibrant greenery and palm trees. The atmosphere is tranquil, ideal for unwinding in a serene setting.
Home in Key West
4.97 out of 5 average rating, 260 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

JRating, 5 stars1 week ago
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!
Guest favorite
The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.
Home in Marathon
5 out of 5 average rating, 23 reviews

Spacious lux home, private pool/spa, 80' dock

KelliRating, 5 stars3 weeks ago
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!
Superhost
An aerial view showcases a spacious waterfront home surrounded by lush greenery and palm trees. A private heated pool is bordered by a white fence, with lounge chairs and umbrellas nearby. A boat dock extends into the water, enhancing the serene setting.
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.

Condo rentals with a pool

Superhost
A community pool is shown, featuring a clear blue water surface with visible lane markings. Surrounding the pool are lounge areas with light-colored decking and palm trees in the background, adding to the open and airy feel of the space.
Condo in Key West
4.83 out of 5 average rating, 276 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

MichaelRating, 5 stars1 month ago
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!
Guest favorite
A bright and airy living area features a comfortable sofa in shades of grey and white, contrasted by decorative blue pillows. A glass coffee table sits on a patterned rug, and large windows allow ample natural light. A dining area is visible in the background.
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 favorite
A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.
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.
Top guest favorite
The image showcases a clear blue pool surrounded by lounge chairs with bright umbrellas, set against the backdrop of the ocean. A sandy beach extends nearby, with a distant building featuring multiple balconies. Fluffy clouds dot the sunny sky above.
Condo in Marathon
5 out of 5 average rating, 15 reviews

*NEW* Kokomo Views-Pool/Beach

AnnRating, 5 stars3 weeks ago
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
Guest favorite
A large swimming pool is surrounded by palm trees and lounge chairs. Sun umbrellas provide shade near the water's edge. The inviting blue water reflects the clear sky above, contributing to a relaxing outdoor space ideal for leisure and socializing.
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 favorite
A spacious outdoor pool area is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool, reflecting a serene atmosphere. A shaded gazebo offers a relaxing spot nearby, while the clear water invites refreshment under the bright sky.
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 favorite
A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.
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 favorite
An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.
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.

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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