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Vacation rentals with a pool in Florida Keys

Find and book unique homes with a pool on Airbnb

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Popular amenities for Florida Keys rentals with a pool

House rentals with a pool

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, 135 reviews

Cancellation Deal: 07/26 thru 08/09

VictoriaRating, 5 stars4 weeks ago
Eddie’s place was perfect for our family vacation! It was beautifully furnished and decorated. The house was clean and clutter free. There were plenty of linens and towels. The kitchen had everything you need and was well organized. The pool area was so relaxing. The location was incredibly convenient to grocery stores and activities as well as just a short walk to the beach which also had a park and great playground for kids. We hope to come back again soon!
Guest favorite
A clear blue sky with scattered clouds is visible above the pool area. Palm trees line the edge of the space, providing a tropical feel. A rectangular pool and a smaller octagonal pool are present, surrounded by lounge chairs and an open expanse of sandy ground.
Home in Cudjoe Key
4.97 out of 5 average rating, 159 reviews

Cudjoe Key Home with a View

RobRating, 5 stars1 week ago
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!
Top guest favorite
A welcoming entrance to the home features a spacious front porch with double doors framed by large, arched windows. Lush landscaping includes various plants and stones, creating a well-defined pathway leading to the entrance. The architecture incorporates a tile roof and a modern design.
Home in Marco Island
4.98 out of 5 average rating, 49 reviews

Gorgeous Marco Island Pool Home near Mackle Park!

NicholasRating, 5 starstoday
This was the perfect house for a family with small kids. We bikes to the park and walked the trail. Everything was 5 minutes away. Gist was perfect, provided everything we needed and answered all questions. Wonderful first time in Marco island, would rent this place again for sure!
Top guest favorite
The illuminated pool glistens in a tranquil setting, adorned with floating yellow lily candles. Lounge chairs with striped towels are positioned beside the water, while soft lights provide ambiance around the area, creating a serene space for relaxation.
Home in Marco Island
4.98 out of 5 average rating, 131 reviews

Top-rated luxury pool home in prime location

SaraRating, 5 stars1 month ago
Our family of four had a great stay at Kate's property. It is in a great location close to beaches and restaurants yet private enough to really be able to relax quietly by the pool. The house is spacious and had all of the amenities we needed for a terrific vacation.
Guest favorite
The exterior of the house features a private pool surrounded by a spacious grassy area. A wooden deck with seating is situated at the back, providing a relaxing spot to enjoy the outdoors. Lush palm trees frame the setting, creating a serene atmosphere.
Home in Pompano Beach
4.97 out of 5 average rating, 117 reviews

•Floasis• Your private FL oasis 5 min to beach!

TravisRating, 5 stars2 weeks ago
Cristina has made a very special place to enjoy with your family/ friends. I felt right at home, and my son started walking alone as soon as he arrived, but he didn’t stop, lol 😆 . That’s the type of energy Cristina Airbnb brings to the table. Keep up the fantastic job. I can’t wait to try one of your other places :)
Top guest favorite
An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.
Home in Key Colony Beach
5 out of 5 average rating, 17 reviews

Bohemian Beach Bungalow

DeborahRating, 5 stars3 weeks ago
The Bohemian Beach Bungalow is amazing! My husband and I can't talk enough about what a wonderful time we had. It was literally one of our best Airbnb stays. Karen our host was great. She answered all our questions so quickly and was very accommodating. Everything is brand new in the house, and it was immaculate inside. We will definitely be returning next year and can't wait. I will be telling all my friends about this amazing find! Thank you, Karen, for a wonderful vacation!!
Guest favorite
A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.
Home in Cudjoe Key
4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

FlorianRating, 5 stars2 weeks ago
There were five of us in the house and we felt immediately comfortable. Everything was super clean. The location right on the water was overwhelming as expected. Everything that is needed was there. The kitchen and terrace were very large and the mattresses were very comfortable. Key West is about 30 minutes away. Check-in and check-out as well as contact were completely unproblematic. We will be back!
Guest favorite
A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.
Home in Marathon
4.96 out of 5 average rating, 113 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JasonRating, 5 stars1 week ago
We really enjoyed this home in Marathon. Sitting by the canal for morning coffee, swimming in the pool on a hot afternoon, having dinner on the covered porch, or plying corn hole on the roof… it was all super enjoyable. Andy even dropped off some wonderful bagels one morning! The location is super close to all that Marathon has to offer. We would recommend this home to anyone

Condo rentals with a pool

Guest favorite
A large pool area is surrounded by lounge chairs and lush greenery. Towering residential buildings are visible in the background, with clear blue skies above. The pool invites guests for a refreshing swim, contributing to a relaxed atmosphere.
Condo in Miami
4.9 out of 5 average rating, 173 reviews

Feels Like Summer ~ Panoramic Water Views! 2BR

ThomasRating, 5 stars2 weeks ago
Wow! What a fabulous apartment! We had the most amazing stay to celebrate my birthday! This apartment had everything we needed, a home from home! Immaculate throughout and in such a central location with AMAZING views!! These hosts were fantastic! Thank you so much! If you’re looking to stay in Miami, this is the one to book!
Guest favorite
A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.
Condo in Key Largo
4.93 out of 5 average rating, 107 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

JodiRating, 5 stars4 weeks ago
Would definitely rent again! Relaxing with plenty of outdoor spaces to enjoy. Comfortable condo with everything you need.
Guest favorite
A spacious living room features a light color palette with a large flat-screen television mounted on the wall. Comfortable seating is arranged around a coffee table, and large windows provide a view of the ocean and natural light. Coastal decor enhances the atmosphere.
Condo in Tavernier
4.9 out of 5 average rating, 124 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

WilliamRating, 5 stars4 days ago
This was a great place to stay in Tavanier! Very close to Key Largo and a short drive to all the charters and activities in Islmarada. Very roomy condo with every at home convenience. Great community pool that had food and drinks available on site from Island Grill. Will definitely consider staying here again. Also.....our host "Largo" was great to deal with. Nice, Friendly, and quick to answer any questions. My boys and I had a wonderful stay!
Superhost
Aerial view of a resort pool area features multiple swimming pools surrounded by palm trees. Lounge chairs are positioned around the pools, some offering shade under canopies. Clear blue water reflects the sky, while buildings in the background complete the resort atmosphere.
Condo in Hollywood
4.92 out of 5 average rating, 132 reviews

Beachfront and Lovely Unit Near Aventura Mall

HaileyRating, 5 stars1 week ago
Nice apartment on the beach with a gorgeous view. Just was super easy to get ahold of and helped us to check in early. 10/10 would recommend!
Top guest favorite
A light-filled living space features a turquoise sofa with yellow accent pillows, paired with a round glass dining table. Rattan chairs complement the decor, which includes a vibrant tropical wall mural and a circular mirror. Modern appliances are visible in the kitchen area.
Condo in Tavernier
4.95 out of 5 average rating, 190 reviews

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba

TimothyRating, 5 stars2 weeks ago
Laurie and Co. were so responsive and welcoming. The place is beautiful and the amenities are lovely. Much like the other reviews, we had a wonderful stay and totally recommend this place!
Guest favorite
A large outdoor pool is surrounded by lounge chairs and shaded umbrellas. Lush palm trees and tropical foliage create a serene atmosphere. Guests can be seen enjoying the water under a clear blue sky, contributing to a relaxed community setting.
Condo in Tavernier
4.94 out of 5 average rating, 103 reviews

Sugar Cane - Florida Keys tropical retreat

KarrinaRating, 5 stars3 weeks ago
Had a great time here. Enjoyed the beach and pool along with the location.
Guest favorite
Condo in Tavernier
4.94 out of 5 average rating, 142 reviews

Keys Life Ocean Pointe Pool Jacuzzi Beach Crib

StefRating, 5 stars3 weeks ago
My family had a wonderful time. The property was clean and well-appointed. Responses from our hosts were always super-quick. I highly recommend!
Guest favorite
A spacious living area features a light and airy design with coastal decor. Large windows offer views of the ocean, while a modern flat-screen television is mounted on the wall. A marble countertop provides a stylish separation from the kitchen area, and natural light enhances the overall ambiance.
Condo in Tavernier
4.96 out of 5 average rating, 138 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

CaroleRating, 5 stars1 month ago
Beautiful condo… met our needs plus…resort was perfect…great location…..very satisfied with this experience

Home rentals with a private pool

A spacious living area is featured, showcasing a comfortable sectional sofa, a TV stand with a large smart TV, and an inviting dining space in the background. Natural light floods the room through sliding doors, enhancing the open design layout. Stylish bar stools line a counter that connects to the kitchen.
Home in Dania Beach
4.25 out of 5 average rating, 4 reviews

Private Villa with Pool, Sauna, Billiard

eric Rating, 5 stars4 weeks ago
It was perfect. We will definitely come back.
The exterior showcases a welcoming entrance with a modern front door framed by bright landscaping. Lush green grass and palm trees line the pathway, leading to the house. A serene sunset casts a warm glow over the facade, enhancing the inviting ambiance of the property.
Home in Marco Island
4.84 out of 5 average rating, 19 reviews

Sandcastle of Marco Island Waterfront Private Pool

CatherineRating, 5 stars1 month ago
Our family came to Marco Beach for our school spring break. What stood out about this house with how close it is to everything. We loved being able to walk to restaurants, coffee, shops, and even the grocery store. The inside of the house was perfect for what we needed. We also greatly enjoyed the pool as well as being able to sit on the dock and look out at the water. Denise, the homeowner, was very easy to work with and was great about giving us recommendations of different things that we could see or do while there. I would highly recommend this property to anybody who is coming to Marco Island, and looking for a place where they can kick back unwind and really enjoy themselves. We will absolutely be back.
An open kitchen features modern appliances, positioned alongside a spacious island with seating. Dark cabinetry contrasts with light countertops, and natural light streams in through large windows. A dining area and living space are visible in the background, enhancing the overall spaciousness.
Condo in Marco Island

Magnificent Gulf View Condo

GabrielleRating, 5 stars29 months ago
The host was responsive and helpful. Fantastic location and views of the ocean! Three pools and three hot tubs, private beach, gym, pickle ball, basketball, etc. so lots to do for families with kids. Beautiful condo, clean, modern, and updated. Peaceful, gorgeous spot on Marco Island - highly recommend!
Home in Marco Island
4.71 out of 5 average rating, 14 reviews

Lighthouse 1124

JoshuaRating, 5 stars6 months ago
Great place to stay in Marco Island. Some minor issues but the host and management are very responsive.
Top guest favorite
A serene outdoor area features a heated saltwater pool surrounded by lounge chairs. A large umbrella offers shade, while the covered patio with seating is visible in the background. Lush greenery adds to the tranquil atmosphere of the space.
Home in Fort Lauderdale
5 out of 5 average rating, 20 reviews

Luxury Waterfront Home Minutes from the Beach

JenelleRating, 5 stars7 months ago
We LOVED our stay in Fort Lauderdale. The place was absolutely beautiful and just like advertised. We had to make a last minute reservation and the hosts were more than accommodating and extremely responsive. We traveled with a family of 6 and the home was the perfect size for us as there was more than enough room and we all had our own bathrooms. The outside area was amazing. The kids loved the pool and it was a very nice quiet, well kept neighborhood. Anytime I had a question I was able to text the hosts and they responded to me almost immediately. I even accidentally sent an amazon package to the wrong address and they offered to bring it to UPS for me. I cant say enough great things about this place, it was close enough to everything that you would need but also private enough to be able to relax when needed. We will definitely be back to Fort Lauderdale and would love to rent this wonderful home again.
Condo in Hollywood

Incredible Beach Getaway Condo W Resort Amenities

Condo in Marco Island

New! Gulf-View Condo with Resort-Style Amenities

A spacious balcony is furnished with a round table and two wicker chairs, offering views of the surrounding cityscape. Large sliding glass doors reflect the bright blue sky and nearby buildings, enhancing the airy atmosphere of the outdoor space.
Condo in Hollywood

Private 2br Side Ocean View at Hyde Beach Resort

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