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Vacation 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

Guest favorite
A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.
Home in Key West
4.9 out of 5 average rating, 91 reviews

Gone Coastal

JimRating, 5 stars2 weeks ago
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.
Superhost
A private outdoor space is featured, showcasing a clear blue pool surrounded by lounge chairs and a dining area with chic striped umbrellas. Lush palm trees provide shade, while a stone pathway leads to the waterfront, enhancing the coastal ambiance.
Home in Islamorada
5 out of 5 average rating, 3 reviews

Islamorada Cay Home. Elegant home

MarlaRating, 5 stars1 month ago
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!
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars17 months ago
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
Superhost
A private pool glistens under the sun, surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. In the background, a tiki palapa with a thatched roof offers shaded seating, complemented by lush tropical foliage and a distant pink house.
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars6 days ago
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!
Guest favorite
Home in Key Colony Beach
4.97 out of 5 average rating, 36 reviews

P23 - New 3 bedroom 2 bath duplex with private po

AndreaRating, 5 stars13 months ago
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!
Superhost
A private heated pool is surrounded by wooden decking and lush landscaping. The exterior features light grey siding, large windows, and a covered outdoor dining area. Relaxing lounge chairs are positioned beside the pool, inviting guests to enjoy the tranquil setting.
Home in Key West
4.9 out of 5 average rating, 143 reviews

A Royal Escape in Key West

ChristinaRating, 5 stars3 months ago
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.
Superhost
A private pool area is surrounded by tropical landscaping, featuring lush greenery. Several lounge chairs with blue and white stripes are positioned around the pool, inviting relaxation. Bright sunshine casts light across the tranquil water, enhancing the peaceful outdoor setting.
Home in Key West
5 out of 5 average rating, 9 reviews

Casablanca ~ Fabulous Home w/ Private Pool/Parking

KathleenRating, 5 stars2 months ago
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.
Superhost
Home in Marathon
4.73 out of 5 average rating, 59 reviews

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage

BryanRating, 5 stars2 months ago
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

Superhost
The room features two spacious beds with crisp white bedding and decorative pillows. Light-colored walls complement the beach-themed artwork. Plantation shutters allow natural light to filter in, and bedside tables with lamps are positioned between the beds. A ceiling fan enhances comfort in the space.
Condo in Key Colony Beach
4.75 out of 5 average rating, 164 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

RobertRating, 5 stars3 weeks ago
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!
Superhost
A spacious living area features a light-colored marble floor and contemporary furnishings. A large flat-screen TV is mounted on an entertainment unit, while comfortable blue sofas are arranged around a glass-top table. A mirrored wall enhances the openness, with the kitchen area visible in the background.
Condo in Key West
4.68 out of 5 average rating, 85 reviews

BOOK today and enjoy our amazing discounts for yo

MarkRating, 5 stars1 month ago
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.
Guest favorite
The Olympic-sized pool is illuminated at night, surrounded by lounge chairs and umbrellas. Lush greenery and palm trees form the backdrop, creating a serene environment for relaxation and recreation.
Condo in Tavernier
4.94 out of 5 average rating, 17 reviews

Resort Condo: Pool | Marina | Beach | Pickleball

SamRating, 5 stars1 week ago
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!
Guest favorite
A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.
Condo in Key West
4.97 out of 5 average rating, 72 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

BrianRating, 5 stars1 week ago
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!
Superhost
A panoramic view showcases the tranquil ocean, framed by palm trees and lush greenery. The scene captures a clear blue sky and the vibrant color of the water, with the outline of nearby buildings visible in the backdrop.
Condo in Key West
4.73 out of 5 average rating, 93 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

JudyRating, 5 stars1 month ago
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!!
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, 138 reviews

Tropical Escape at Sunrise

RobertaRating, 5 stars1 week ago
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.
Superhost
A spacious balcony features a table and four chairs, surrounded by tropical plants. Comfortable seating options are positioned for relaxation, offering views of the calm water and a vibrant sunset in the background.
Condo in Key West
4.75 out of 5 average rating, 4 reviews

Promenade to Paradise at The Annex

AlanRating, 5 stars58 months ago
Absolutely fantastic unit and location, and the communication and service from Last Key was white glove. Top notch. We will be back.
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
4.94 out of 5 average rating, 143 reviews

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

YinanRating, 5 stars3 days ago
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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