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Vacation rentals with a pool in Westchester

Find and book unique homes with a pool on Airbnb

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Popular amenities for Westchester rentals with a pool

House rentals with a pool

Guest favorite

Home in Miami Springs

4.96 out of 5 average rating, 141 reviews

Spanish House 3 Bedroom Pool House

AmandaRating, 5 stars2 weeks ago
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!
Guest favorite

Home in Miami

4.89 out of 5 average rating, 222 reviews

Large heated Pool Home (Centrally Located)

AustinRating, 5 stars1 month ago
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!
Superhost

Home in Cutler Bay

4.96 out of 5 average rating, 141 reviews

Luxe Escape Miami 5BR Heated Pool/ Plays, BB court

CaseyRating, 5 stars3 months ago
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!
Guest favorite

Home in Hollywood

4.95 out of 5 average rating, 130 reviews

LUXURIOUS SUPER HOST HOLLYWOOD HOUSE, POOL HEATER

FernandoRating, 5 stars1 week ago
• house was clean • responded promptly • backyard was fun • very spacious • neighbourhood was great
Guest favorite

Home in North Miami

4.94 out of 5 average rating, 134 reviews

Bright and fun heated POOL home - 5 bedrooms

ShelbyRating, 5 stars6 days ago
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!!
Guest favorite

Home in Hollywood

4.92 out of 5 average rating, 153 reviews

Hard Rock Villa - House With Pool & Selfie Walls

DavyRating, 5 stars1 month ago
I’ve enjoyed my stay here. Private and peaceful environment. I would love if I could stay here again. Very responsive host.
Superhost

Home in Allapattah

4.88 out of 5 average rating, 137 reviews

Urban Oasis With Pool at West Wynwood/Allapattah

TamiresRating, 5 stars1 week ago
Ezequiel is very attentive. The space was spotless.
Guest favorite

Home in Miami

5 out of 5 average rating, 21 reviews

Miami Oasis: Charming home with private pool

VicRating, 5 stars1 month ago
Excelent host. The house is perfect, everything was clean and She always responded very quickly!

Condo rentals with a pool

Superhost

Condo in Sunny Isles Beach

4.9 out of 5 average rating, 10 reviews

le cartier sunny isles ocean paradise

GerbenRating, 5 stars1 week ago
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.
Superhost

Condo in Brickell Business District

4.89 out of 5 average rating, 191 reviews

Luxury Deal!40th Floor*Miami*Sleeps9*RENOVATED!

AngelaRating, 5 stars3 days ago
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.
Superhost

Condo in Sunny Isles Beach

4.89 out of 5 average rating, 105 reviews

Golden Bay Club Beautiful Condo! -STR-02901.

SarahRating, 5 stars2 weeks ago
Nice spacious condo walking distance to the beach in Sunny Isles. Responsive host and no issues throughout the stay.
Superhost

Condo in Hollywood Beach

4.83 out of 5 average rating, 36 reviews

Luxurious 3/3 Resort Condo by the Beach

WinfieldRating, 5 stars3 months ago
Anthony has a great property in a prime location. The view is amazing. Friendly and responsive host. We would stay here again!
Guest favorite

Condo in Miami

4.93 out of 5 average rating, 15 reviews

Modern Spacious 2 Bed In Aventura/ FREE Parking

IvanRating, 5 stars5 months ago
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.
Superhost

Condo in Miami Design District

4.69 out of 5 average rating, 35 reviews

Modern 1BR +Free Parking Pool Gym @Miami Design

StevenRating, 5 stars5 months ago
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!
Superhost

Condo in Key Biscayne

4.88 out of 5 average rating, 32 reviews

Ocean Breeze

PeterRating, 5 stars8 months ago
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!
Guest favorite

Condo in Sunny Isles Beach

5 out of 5 average rating, 22 reviews

Oceanfront Remodeled Beautiful Condo

DianaRating, 5 stars1 month ago
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.

Quick stats about vacation rentals with a pool in Westchester

  • Total rentals

    30 properties

  • Nightly prices starting at

    $70 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

Destinations to explore