
Vacation 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.
Vacation rentals for every style
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Popular amenities for Westchester rentals with a pool
House rentals with a pool

Miami 3/2 with Pool Home
The house was extremely nice and exactly what we were looking for. The rules were not hard to follow at all. The pool and outside seating area was where we spent the most of our time. If I come back to Miami I will definitely check to see if this house is available first!

Spanish House 3 Bedroom Pool House
This place was amazing! There was lots to do for people of all ages. The place was super clean and Lesliet was very welcoming and willing to assist with every request. A great find!

Large 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!

LUXURIOUS SUPER HOST HOLLYWOOD HOUSE, POOL HEATER
The was one of the better vacation rental experiences I have had. Everything in the house was in great condition and working order.

Bright and fun heated POOL home - 5 bedrooms
reasonable price, looks exactly like the pictures, easy check in

Hard Rock Villa - House With Pool & Selfie Walls
Easy to find and nice keypad entry! House had a LOT of room - we had 5 adults and we could easily spread out. We used 3 bedrooms - with the 4th bedroom (with a desk) used as an office. Seating available for 6 in the dining room; kitchen updated and very handy! Linens and towels were ample. Washer & dryer were also nice to have. We enjoyed sitting outside by the pool with the colorful wall murals!! The house is on a dead-end; NO traffic noise; a park is located across the street. We had easy access to University Drive - and all the retail and restaurants it had in close proximity. It was also easy to get to The Guitar Hotel and Casino; Hard Rock Stadium; the beaches, and all points North and South! Great LOCATION! Joseph was also GREAT to work with - FRIENDLY and TIMELY communication!!

Modern home, Pool & Grill
Santi’s place was great. Outdoor area was fantastic. Nice to have the beverage fridge and ice in the outdoor cooking area (and the grill itself was top of the line). House was spotless. Santi was responsive and informative. Very good overall experience. He made it a pleasure to rent from him. No issues whatsoever.

Urban Oasis With Pool at West Wynwood/Allapattah
Great place
Condo rentals with a pool

le cartier sunny isles ocean paradise
An excellent apartment and location. Fully equipped to make you feel at home. Vickie was very helpful and kind to us, she gave us great answers to our needs. We would be hesitating again!!

Luxury Deal!40th Floor*Miami*Sleeps9*RENOVATED!
Our daughter and mama getaway was a huge success!! We loved our accommodations. The condo was beautiful and located in the heart of the city. The views from the balcony were breathtaking! Restaurants and shopping were all in walking distance. We highly recommend!! We are already talking about booking again!! The hosts were amazing, helpful and very genuine. We appreciate the quick response and appreciated the early check in! We had a blast and will hopefully book again soon!! Thanks for such an amazing experience!

Golden 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.

Luxurious 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!

Modern Spacious 2 Bed In Aventura/ FREE Parking
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.

SoBe condo with amazing views
Had a pleasant stay! This Airbnb is located in a beautiful, large luxury building in a perfect area of south beach! Building has many upscale amenities like fitness center, pool etc. The host was very responsive and if there was an issue it was handled swiftly. Would recommend!

Modern 1BR +Free Parking Pool Gym @Miami Design
The best a vacation Airbnb so far in my life

Oceanfront Remodeled Beautiful Condo
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!
Home rentals with a private pool

Private Villa with Pool, Sauna, Billiard
great place

Private 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.
Quick stats about vacation rentals with a pool in Westchester
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
1.5K 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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- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Hard Rock Stadium
- Ocean Terrace Public Beach
- John Pennekamp Coral Reef State Park
- Broward Center for the Performing Arts
- Trump National Doral Miami
- Key Biscayne Beach
- Zoo Miami
- Crandon Beach
- Biltmore Golf Course Miami
- Anne Kolb Nature Center
- Miami Beach Golf Club
- Palm Aire Country Club
- Monkey Jungle
- Boca Dunes Golf & Country Club
- Jungle Island
- Port Everglades
- Gulfstream Park Racing and Casino
- Dania Beach
- Margaret Pace Park
- Venetian Pool
- Deering Estate