
Holiday rentals with a pool in Florida Keys
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Florida Keys
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Florida Keys rentals with a pool
House rentals with a pool

Cancellation Deal: 08/02 thru 08/09
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!

Cudjoe Key Home with a View
The house is located in a peaceful community with a store inside that was perfect because you don’t have to drive to get basic necessities. Pool and spa were perfect. And the view is magical. The house was cleaned and beautifully decorated. The outside areas were perfect too. I loved take breakfast on the porch.

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

•Floasis• Your private FL oasis 5 min to beach!
Cristina’s place was lovely! We really enjoyed our time in the pool and hot tub and really got a lot of time to relax! She was responsive and more than helpful! We traveled with a toddler and she had a pack n play and a highchair for us along with recommendations for child friendly activities!

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

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

Anglers Terrace, Condé Nast Traveler's Best Airbnb
The house was beautiful!We thoroughly enjoyed all the outdoor spaces.With 4 bedrooms and an 8 month old, the house offered many spaces for everyone to be comfortable. The beds were comfortable and we were all well rested. The rooftop area for grilling and chilling was amazing. The outdoor seating area off the main level was where we celebrated Father’s Day dinner. Morning snuggles were spent in the seating area off the den.The pool area was where we laughed and swam and had many a cocktail. We loved our week as a family there and had no reason to leave except for a few dinners out.Andy was very responsive, dropped off bagels one morning and a great resource for recommendations. Highly recommend Anglers Terrace as we loved our week there!

Sunset Serenity | Heated Pool | SPA |5min Beach
It was a wonderful six days! Being able to bring my dog was great💙house was exactly as pictured…great experience, thank you Rachell!
Condo rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR
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!

Luxury Beach & City View Condo 5 min walk to beach
I took my teenage girls here for our summer vacation. The location was perfect. The condo and pool was exactly as pictured. The beach is walking distance. My girls lived there lights (in their words “it was an entire vibe”). Joe and Cindy were super responsive to the questions I had. I highly recommend!!

Chic Studio 5 Icon Brickell Amazing View
The place was beautiful looked even better than the photos, the bed was super comfortable, view was extremely beautiful, only problem was I wish it was more towels I asked for them but nobody ever brought them. Other than that everything was great, also be prepared to pay at least $40-50 a day for parking. Great host he was there right away to help with check in and gave us a better rate for parking which was $40 a day.

Your Happy Place - Oceanfront
Sandra's place was very nice and clean. She was very reponsive with any and all questions. The accomodations are as listed. I enjoyed the peace and quiet. I most enjoyed relaxing on the balcony listening to the ocean. All you need is you, clothes, and the memories you will make. The rest is provided. However I will note that I was expecting a "real" beach and it was more of a lagoon. although still nice. Thanks Sabdra I would definitely book again. 🙂

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
This is a top notch airbnb. Excellent communication from the host, extremely clean, well stocked condo, generous supplies beautiful decor. We stayed 8 days in the condo and felt right at home. Loved the large pool. We caught many fish and cooked at the condo all but 2 evenings and had everything we needed to prepare meals. Really appreciated the assortment of coolers provided for day trips. Thank you again, John!

Florida Keys Getaway - Slps 4 - Ocean View
We had a fantastic stay. Melanie gave us some good recommendations and was quick to respond. The apartment had everything we needed. We made use of the pool, bar and restaurant and we love watching the wildlife from the balcony. We would definitely stay here again!!

Upper Penthouse Corner Unit 2B/2B | Icon Brickell
My 2 daughters and I had a wonderful stay at Alican Penthouse. The place was spotless, tastefully decorated, and had all the essentials. The view from the balcony was breathtaking, especially at night. It was a peaceful escape with restaurants, spas, gyms, hot and cold pools on site but still just a 10-minute drive from the restaurants , beaches, clubs, shops and malls. Looking forward to another visit.

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
We really enjoyed our stay Beautiful condo extremely clean clear instructions wonderful place to stay pool and hot tub area are amazing. You can swim anytime which is really nice. Most places the pool closes at dusk. There is a nice poolside little restaurant and also a restaurant right by the beach area really convenient would go back there anytime
Home rentals with a private pool

Private Villa with Pool, Sauna, Billiard
We had such a wonderful stay at this beautiful home for our baby shower weekend! It was the perfect space to host a small, family gathering that was clean, spacious, and full of charm. The pool and game areas made it easy for everyone to relax and have fun, and the location was ideal with the beach nearby and friendly neighbors all around. The host was kind and accommodating, and we truly appreciated being able to celebrate such a special moment in a place that felt like home. Thank you for helping make our weekend so memorable . We’d love to stay again in the future!

Sandcastle of Marco Island Waterfront Private Pool
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.

Magnificent Gulf View Condo
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!

Lighthouse 1124
Red Awning and this house was exactly how described. I would 100% stay here again. Clean, quiet

Incredible Beach Getaway Condo W Resort Amenities

New! Gulf-View Condo with Resort-Style Amenities

Private 2br Side Ocean View at Hyde Beach Resort
Destinations to explore
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Key West Holiday rentals
- Havana Holiday rentals
- Central Florida Holiday rentals
- Tampa Bay Holiday rentals
- Kissimmee Holiday rentals
- St Petersburg Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Rentals with a sauna Florida Keys
- Beach house rentals Florida Keys
- Fitness-friendly rentals Florida Keys
- Houseboat rentals Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Smoking-friendly rentals Florida Keys
- Apartment rentals Florida Keys
- Rentals with beach access Florida Keys
- Boutique hotel rentals Florida Keys
- RV rentals Florida Keys
- Villa rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Rentals with lake access Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Bed and breakfasts Florida Keys
- Hotel rentals Florida Keys
- Cottage rentals Florida Keys
- Tiny house rentals Florida Keys
- Bungalow rentals Florida Keys
- Kid-friendly rentals Florida Keys
- Rentals with a fire pit Florida Keys
- Private suite rentals Florida Keys
- Rentals with an accessible height bed Florida Keys
- Beachfront rentals Florida Keys
- House rentals Florida Keys
- Townhouse rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Pet-friendly rentals Florida Keys
- Family-friendly rentals Florida Keys
- Luxury rentals Florida Keys
- Rentals with a washing machine and dryer Florida Keys
- Rentals with a fireplace Florida Keys
- Campsite rentals Florida Keys
- Rentals with breakfast Florida Keys
- Serviced apartment rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Rentals with a patio Florida Keys
- Rentals with a home theatre Florida Keys
- Resort rentals Florida Keys
- Rentals with a kayak Florida Keys
- Condo rentals Florida Keys
- Waterfront rentals Florida Keys
- Beach condo rentals Florida Keys
- Guesthouse rentals Florida Keys
- Mansion rentals Florida Keys
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Bayfront Park
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Trump National Doral Miami
- Crandon Beach
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Coral Castle
- Hobie Island Beach Park North
- Cannon Beach
- Biltmore Golf Course Miami
- Fairchild Tropical Botanic Garden
- Biscayne National Park
- Conch Key
- Venetian Pool
- Everglades Alligator Farm
- Theater of the Sea
- Matheson Hammock Park
- Miami Seaquarium
- Cocoa Plum Beach
- EAA Air Museum
- Virginia Beach
- Things to do Florida Keys
- Tours Florida Keys
- Sightseeing Florida Keys
- Art and culture Florida Keys
- Sports activities Florida Keys
- Things to do Florida
- Wellness Florida
- Entertainment Florida
- Food and drink Florida
- Sightseeing Florida
- Tours Florida
- Art and culture Florida
- Sports activities Florida
- Nature and outdoors Florida
- Things to do United States
- Sports activities United States
- Nature and outdoors United States
- Art and culture United States
- Wellness United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States