Holiday rentals with a pool in Westchester
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westchester
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Westchester rentals with a pool
House rentals with a pool
Home in Miami Springs
4.96 out of 5 average rating, 141 reviewsSpanish House 3 Bedroom Pool House
We stayed here before a cruise for 3 nights, 4 adults and 2 kids. The house was awesome and so spacious for us all. The kids lived in the pool and we enjoyed the bbq and outdoor space. The kitchen was well stocked and we were able to make some simple meals for us all. Lesliet was super accommodating with us coming on a late flight from Canada. We were able to place an instacart order and the cleaners were there and put it away for us! Lesliet was very quick to respond to questions and assisted us beyond expectations. We loved having the washer and dryer, clean suitcases before a cruise was so nice! Would stay here again if we come back!
Home in Miami
4.89 out of 5 average rating, 222 reviewsLarge heated Pool Home (Centrally Located)
Arriving from very cold weather up north, Claudia’s warm welcome was just what we needed! Her lovely home felt like our own mini-resort—from the pool and hot tub (which she turned on each evening for us) to the fresh flowers and potted poinsettias, the pickleball court, comfy beds and sofas, beach and bath towels galore. She even supplied beach chairs and a cart for us when we headed to Biscayne Bay for a day. Claudia’s hospitality was truly exceptional, and her home perfectly located for exploring favorite spots: Vizcaya, Fairchild Tropical Gardens, Wynwood walls, a trove of great restaurants, and more. We had a wonderful time!
Home in Cutler Bay
4.96 out of 5 average rating, 141 reviewsLuxe Escape Miami 5BR Heated Pool/ Plays, BB court
It was the perfect house for a large party. It was very clean and Nani was very helpful with recommendations. We will definitely keep this place in mind for future Miami vacays!
Home in Hollywood
4.95 out of 5 average rating, 130 reviewsLUXURIOUS SUPER HOST HOLLYWOOD HOUSE, POOL HEATER
• house was clean • responded promptly • backyard was fun • very spacious • neighbourhood was great
Home in North Miami
4.94 out of 5 average rating, 134 reviewsBright and fun heated POOL home - 5 bedrooms
my friends & i came to miami for the week, this place was perfect! everything we wanted to do was within 30 minutes from the house. the house was clean & comfortable & fit everyone that came. the heated pool was the highlight of the house and was the perfect thing to do at night to unwind after doing activities during the day. we all would definitely recommend this place to anyone & will be booking again in the future. thanks so much again alex!!
Home in Hollywood
4.92 out of 5 average rating, 153 reviewsHard Rock Villa - House With Pool & Selfie Walls
I’ve enjoyed my stay here. Private and peaceful environment. I would love if I could stay here again. Very responsive host.
Home in Allapattah
4.88 out of 5 average rating, 137 reviewsUrban Oasis With Pool at West Wynwood/Allapattah
Ezequiel is very attentive. The space was spotless.
Home in Miami
5 out of 5 average rating, 21 reviewsMiami Oasis: Charming home with private pool
Excelent host. The house is perfect, everything was clean and She always responded very quickly!
Condo rentals with a pool
Condo in Sunny Isles Beach
4.9 out of 5 average rating, 10 reviewsle cartier sunny isles ocean paradise
Great place to stay near the beach (7min walk) and near a grocery store (10min walk). Includes a dedicated parking spot and private pool. Vickie is friendly, proactive as well as very responsive. One slight flaw was the building manager said there was no crib and high chair upon check in which was a shock as we traveled with a baby. It turned out both were available (as well as some amazing toys); the building manager just needs to be more aware what is in the property, but Vickie smoothened that out.
Condo in Brickell Business District
4.89 out of 5 average rating, 191 reviewsLuxury Deal!40th Floor*Miami*Sleeps9*RENOVATED!
Our stay was great and the location was unmatched - we were able to walk to restaurants and activities and our Airbnb had a fantastic view. Even when we did run into hiccups that were out of the hosts control, they were responsive and did their best to make sure we were comfortable.
Condo in Sunny Isles Beach
4.89 out of 5 average rating, 105 reviewsGolden Bay Club Beautiful Condo! -STR-02901.
Nice spacious condo walking distance to the beach in Sunny Isles. Responsive host and no issues throughout the stay.
Condo in Hollywood Beach
4.83 out of 5 average rating, 36 reviewsLuxurious 3/3 Resort Condo by the Beach
Anthony has a great property in a prime location. The view is amazing. Friendly and responsive host. We would stay here again!
Condo in Miami
4.93 out of 5 average rating, 15 reviewsModern Spacious 2 Bed In Aventura/ FREE Parking
10/10 stayed for 2 weeks and just made out extended stay easier. Awesome location and a really great environment to be in. Awesome apartment with all the amenities you need. And an extra note awesome attentiveness from out host to our need and accommodation to help us in any way on out stay.
Condo in Miami Design District
4.69 out of 5 average rating, 35 reviewsModern 1BR +Free Parking Pool Gym @Miami Design
Beautiful building, very clean, everything you could need from an apartment. Loved the bbq and pool area on the 6th floor. Only slight issue was the noise from the road at night but it’s to be expected in a lively city like Miami. Dani was a great host!
Condo in Key Biscayne
4.88 out of 5 average rating, 32 reviewsOcean Breeze
Great value for the price, especially considering the neighborhood of Key Biscayne, which offers few lodging options that are affordable. Many things to do, all within reasonable walking distance, including public beach access. Overall a great find, one I hope to repeat one day!
Condo in Sunny Isles Beach
5 out of 5 average rating, 22 reviewsOceanfront Remodeled Beautiful Condo
We had an amazing stay. incredible condo, extremely clean, organized, all the amenities needed. Fantastic location, on the beach, close to many great restaurants, shopping and entertainment.
Home rentals with a private pool
Villa in Miami
3.13 out of 5 average rating, 8 reviewsPrivate Luxury Spanish Style Home W Private Pool
Although this location is much closer to Ft. Lauderdale than Miami, it was beautiful and spacious. We felt safe and loved the pool! Would definitely recommend.
Home in Dania Beach
4 out of 5 average rating, 3 reviewsPrivate Villa with Pool and Sauna
great place
Villa in Cutler Bay
5 out of 5 average rating, 6 reviewsLuxury Escape: Pool, Hot Tub, Mini Golf, & More!
Very flexible space for a large group of people. Very clean and modern. Pool and Jacuzzi we clean and will kept. Would stay here again for sure.
Quick stats about holiday rentals with a pool in Westchester
Total rentals
30 properties
Nightly prices starting at
$113 AUD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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