Holiday rentals with a pool in Florida Keys

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Florida Keys rentals with a pool

House rentals with a pool

Top Guest favourite
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 favourite
Home in Cudjoe Key
4.97 out of 5 average rating, 160 reviews

Cudjoe Key Home with a View

YirenyRating, 5 stars2 weeks ago
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.
Top Guest favourite
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.
Guest favourite
Home in Pompano Beach
4.97 out of 5 average rating, 119 reviews

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

AnnaRating, 5 stars1 week ago
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!
Guest favourite
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!
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars1 month ago
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 115 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

SusanneRating, 5 stars2 days ago
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!
Top Guest favourite
Home in Marco Island
4.96 out of 5 average rating, 23 reviews

Sunset Serenity | Heated Pool | SPA |5min Beach

ChristineRating, 5 stars3 weeks ago
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

Guest favourite
Condo in Miami
4.9 out of 5 average rating, 174 reviews

Feels Like Summer ~ Panoramic Water Views! 2BR

ThomasRating, 5 stars4 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 favourite
Condo in Sunny Isles Beach
4.91 out of 5 average rating, 105 reviews

Luxury Beach & City View Condo 5 min walk to beach

KimRating, 5 stars2 weeks ago
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!!
Superhost
Condo in Miami
4.86 out of 5 average rating, 160 reviews

Chic Studio 5 Icon Brickell Amazing View

NatashaRating, 5 stars1 week ago
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.
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 101 reviews

Your Happy Place - Oceanfront

RodRating, 5 stars1 week ago
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. 🙂
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 146 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

KatieRating, 5 stars3 weeks ago
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!
Superhost
Condo in Tavernier
4.77 out of 5 average rating, 370 reviews

Florida Keys Getaway - Slps 4 - Ocean View

JulieRating, 5 stars4 days ago
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!!
Guest favourite
Condo in Miami
4.95 out of 5 average rating, 121 reviews

Upper Penthouse Corner Unit 2B/2B | Icon Brickell

HeatherRating, 5 stars3 weeks ago
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.
Guest favourite
Condo in Tavernier
4.95 out of 5 average rating, 128 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

NicholasRating, 5 stars6 days ago
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

Home in Dania Beach
4.4 out of 5 average rating, 5 reviews

Private Villa with Pool, Sauna, Billiard

SarahRating, 5 stars2 weeks ago
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!
Home in Marco Island
4.84 out of 5 average rating, 19 reviews

Sandcastle of Marco Island Waterfront Private Pool

CatherineRating, 5 stars2 months 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.
Condo in Marco Island

Magnificent Gulf View Condo

GabrielleRating, 5 stars30 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
4.73 out of 5 average rating, 15 reviews

Lighthouse 1124

RalphRating, 5 stars1 month ago
Red Awning and this house was exactly how described. I would 100% stay here again. Clean, quiet
Condo in Hollywood

Incredible Beach Getaway Condo W Resort Amenities

Condo in Marco Island

New! Gulf-View Condo with Resort-Style Amenities

Condo in Hollywood

Private 2br Side Ocean View at Hyde Beach Resort

Destinations to explore