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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

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 stars2 weeks 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!
Top guest favorite
A shaded porch area features comfortable seating with patterned cushions and a blue-framed bench. A table with chairs is seen nearby, set on a textured outdoor rug that enhances the space. Two ceiling fans are installed above for added comfort.
Home in Key West
5 out of 5 average rating, 7 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

AmyRating, 5 stars2 weeks ago
We had a great time at Judy’s airbnb. It was super nice, clean and had really comfortable beds. The pool was right across the parking area, very clean, private and always had chairs available. Over all our stay was great and we will definitely be back.
Guest favorite
A quaint outdoor seating area features a round glass table surrounded by two wicker chairs, each adorned with colorful cushions. A decorative wall panel with a Buddha motif adds an artistic touch, while large windows invite ample natural light into the space.
Home in Key West
5 out of 5 average rating, 23 reviews

Catherine House: A charming Old Town Key West

MichaelRating, 5 stars2 months ago
We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!
Superhost
Home in Key Colony Beach
4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

BrittanyRating, 5 stars31 months ago
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.
Guest favorite
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars1 week ago
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!
Superhost
Home in Marathon
4.74 out of 5 average rating, 61 reviews

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

BethRating, 5 stars2 weeks ago
It really is the perfect place to stay. We picked this house after our last trip to FL where we rented a beach house only to have high winds and man of war jellyfish so couldn't get in the water at all. This place with its amazing hot tub and pool, tons of pool toys and floaties, books and games, would be a wonderful vacation even if you were stuck there the whole time due to bad weather, These owners have done a wonderful job thinking of so many amenities- cozy couch blankets, life jackets, tons of beach equipment, so many dishes and pans and various drink holders. The only complaint I could think of if I had to would be to have another ice tray (there were two semi broken ones but not a big deal as we just bought ice). But that's a pretty small thing in the long list of things that were superb. Even the beds were as soft and as comfortable as mine at home. I hate to let the secret out, but this house is fantastic.
Superhost
A private pool is surrounded by lounge chairs on a concrete patio. The stilted home features a balcony above, supported by pillars. Lush greenery frames the area, while a bright blue sky adds to the inviting atmosphere.
Home in Marathon
4.82 out of 5 average rating, 17 reviews

Sale! Pool, Hot Tub, Dock & Putting Green!

NicoleRating, 5 stars1 month ago
We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!
Top guest favorite
Home in Tavernier
5 out of 5 average rating, 17 reviews

Islamorada Reef Canal & Pool home off Tav Creek-

TiffanyRating, 5 stars1 week ago
Isa was an amazing host! The house is beautiful and pristine! We loved the pool and how close the house is to everything. Our only regret is we couldn’t stay longer!!!! Thank you so much!

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 stars1 month 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!
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, 18 reviews

Resort Condo: Pool | Beach | Marina | Pickleball

SamRating, 5 stars2 weeks 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, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars2 weeks ago
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.
Guest favorite
A large junior Olympic size pool is surrounded by lounge chairs and umbrellas, set against a backdrop of lush tropical greenery. The clear blue water reflects the sky, inviting relaxation in a tranquil environment.
Condo in Tavernier
4.89 out of 5 average rating, 133 reviews

1BR - Key Largo Sun & Sand Hideaway

JosephRating, 5 stars1 week ago
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.
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, 94 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 stars3 weeks 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.
Guest favorite
An aerial view of a large pool area, surrounded by lounge chairs and umbrellas in vibrant colors. Lush greenery and trees border the space, while the ocean can be seen in the distance. A hot tub is positioned near the pool, enhancing the resort-like setting.
Condo in Tavernier
4.9 out of 5 average rating, 281 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

SheilaRating, 5 starstoday
Kimberly was a very responsive host providing clear instructions, local recommendations and checking in on our stay to see if she could help with anything else. The unit was clean and comfortable. Wish the deck was larger was our only negative. The community pool area was great to hang out at with plenty of chairs, lounges and umbrellas. And we enjoyed the poke bowl and cocktails at the on-site grill. Would stay again if in the area.
Guest favorite
An aerial view captures the large swimming pool surrounded by lounge chairs with blue umbrellas. The pool is bordered by tropical landscaping and leads to a scenic stretch of ocean in the background. Nearby, a hot tub and shaded seating areas add to the inviting environment.
Condo in Tavernier
4.94 out of 5 average rating, 140 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

BrianRating, 5 stars2 weeks ago
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again

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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