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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 Fort Lauderdale
4.88 out of 5 average rating, 119 reviews

Beautiful 2/1 home with pool

LeonaRating, 5 stars2 weeks ago
We enjoyed our stay and it suited our purposes perfectly. The pool was lovely and the house had everything we needed from cookware to linens to toiletries. Conveniently located as well. Extra shoutout for Ryan for some great local restaurant recommendations (Serafina Italian restaurant was our fave) and for recommending we take the Brightline train for our day trip to Orlando. Saved us hours of driving and hassle! Thanks for a great stay.
Guest favorite
Home in Hollywood
4.94 out of 5 average rating, 145 reviews

LUXURIOUS SUPER HOST HOLLYWOOD HOUSE, POOL HEATER

NarcisoRating, 5 stars3 days ago
The house is well organized and very clean ,the host always respond an a matter of minutes I give her 10 ⭐️
Guest favorite
Home in North Miami
4.95 out of 5 average rating, 150 reviews

Bright and fun heated POOL home - 5 bedrooms

SilviaRating, 5 stars1 week ago
Highly recommend staying here! Everything provided at this Airbnb was nicely organized and perfect for our group. We had a pleasure of staying here for a couple of days and it was all worthwhile. Thankful for the host for accommodating us too.
Guest favorite
Home in Hollywood
4.92 out of 5 average rating, 158 reviews

Hard Rock Villa - House With Pool & Selfie Walls

DavidRating, 5 stars3 weeks ago
This was a great place to stay. At the end of a road next to a park in a quiet subdivision. The pool was great to have for the family. AC worked great and we had a wonderful time. Host was very responsive and flexible with our needs.
Superhost
Home in Fort Lauderdale
4.89 out of 5 average rating, 102 reviews

Fort Lauderdale Home w/Pool & Private Fenced Yard

LiQi An GRating, 5 stars1 month ago
It's very comfortable and cozy. If I may come to Florida again, stay here again. Thank you.
Superhost
Home in Allapattah
4.86 out of 5 average rating, 151 reviews

Urban Oasis With Pool at West Wynwood/Allapattah

AaronRating, 5 stars1 day ago
Perfect for our short stay! Comfortably accommodated our family of 8 and the location was great. Ezequiel was very responsive with any questions we had.
Guest favorite
Home in Miami
4.95 out of 5 average rating, 146 reviews

Heated Pool/Basketball Court/Ping Pong Table/Golf

AliciaRating, 5 stars2 weeks ago
Me and my family enjoyed our stay! The house was lovely and has plenty for you and your family to do, there will never be a dull moment for the kids. Next time I visit Miami I will be booking this home again!
Guest favorite
Home in Fort Lauderdale
4.94 out of 5 average rating, 177 reviews

Downtown Ft Lauderdale 3 bedroom HEATED Pool Home

TaviaRating, 5 stars3 weeks ago
My family & I visited Florida for a week and Jacks home was PERFECT for us. the neighborhood was very nice and quiet, the home itself was wonderful. We really enjoyed the back yard with pool it was beautiful. Would definitely stay here again! The location is also very convenient.

Condo rentals with a pool

Guest favorite
Condo in Sunny Isles Beach
4.88 out of 5 average rating, 107 reviews

Golden Bay Club Beautiful Condo! -STR-02901.

JimRating, 5 stars3 weeks ago
The apartment is exactly as described. This is a tremendous place to relax, recover and enjoy the sunny isles of Florida. Fernando and team were incredibly gracious and responsive. Would definitely stay there again (hopefully very soon)
Superhost
Condo in Hollywood Beach
4.83 out of 5 average rating, 36 reviews

Luxurious 3/3 Resort Condo by the Beach

WinfieldRating, 5 stars5 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
4.9 out of 5 average rating, 20 reviews

Modern Spacious 2 Bed In Aventura/ FREE Parking

CarolinaRating, 5 stars1 month ago
I recently stayed at a beautiful apartment in Miami, hosted by Dmitry and Maria, and we couldn't have been more pleased with the experience. The apartment offered stunning views of the water and boats, making every moment feel like a picturesque escape. It was impeccably clean, which added to the overall comfort and enjoyment of the stay. Dmitry and Maria were incredibly kind and flexible, always available whenever we needed assistance, making the entire process smooth and pleasant. The beds were comfortable, the bathrooms were very nice, and the kitchen was fully equipped.I highly recommend this apartment for anyone looking to visit Miami.
Guest favorite
Condo in Central Beach
4.81 out of 5 average rating, 73 reviews

Luxury 1/1 Beach Condo *No resort Fee* Pools, Gym

DavianRating, 5 stars1 week ago
Really easy check in. Beautiful place. Felt just at home. Talk about a view! Easy instructions to access everything!
Superhost
Condo in Miami Design District
4.69 out of 5 average rating, 36 reviews

Modern 1BR +Free Parking Pool Gym @Miami Design

PumRating, 5 stars6 months ago
The best a vacation Airbnb so far in my life
Top guest favorite
Condo in Sunny Isles Beach
5 out of 5 average rating, 30 reviews

Oceanfront Remodeled Beautiful Condo

UljanaRating, 5 stars1 month ago
We had a wonderful stay at this condo! The space was clean, well-maintained, and had everything we needed for a comfortable stay. The beautiful ocean view from the spacious balcony was a highlight, and the location couldn't have been better - perfect for easy access to everything nearby. The owner was incredibly helpful and made sure we had all the information we needed. Highly recommend this place for anyone looking for a relaxing getaway!
Guest favorite
Condo in Sunny Isles Beach
4.93 out of 5 average rating, 59 reviews

Beautiful modern 2 bedroom condo across the beach.

RaffaeleRating, 5 stars5 days ago
I am a fan of the Ocean Reserve. Daniel’s apartment stood out for the furniture, the amenities and the parking which is right in front of the building.
Top guest favorite
Condo in Victoria Park
5 out of 5 average rating, 18 reviews

Cozy corner condo, just renovated, pool views

KendallRating, 5 stars1 day ago
Gustavo’s place was exactly what we expected! Nicely decorated, clean and in a really nice peaceful neighborhood. A hidden gem that feels right at home in a big city!

Quick stats about vacation rentals with a pool in Westchester

  • Total rentals

    50 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    3K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

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