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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

Superhost
Home in Miami
4.78 out of 5 average rating, 50 reviews

Miami 3/2 with Pool Home

KristaRating, 5 stars1 week ago
The house was comfortable overall. It was mostly quiet despite houses being close together and being near the airport. Hand soap and lotion were provided but not other toiletries. The pool was very cute and clean, though I only got to stick my legs in since the weather wasn’t hot enough for me to want to go fully in.
Guest favorite
Home in Miami Springs
4.97 out of 5 average rating, 145 reviews

Spanish House 3 Bedroom Pool House

VaughnRating, 5 stars3 weeks ago
This home was absolutely lovely. There was never a time where we were bored. Whether we were just down the road out and about or relaxing in the house playing cards or pool. The backyard was the most relaxing place with the pool, TV, speakers and complete privacy from neighbors. I would 100% recommend staying in this home. Thank you so much to Lesliet for allowing us to stay in your home and being a great host.
Guest favorite
Home in Miami
4.89 out of 5 average rating, 222 reviews

Large heated Pool Home (Centrally Located)

AustinRating, 5 stars2 months 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
4.94 out of 5 average rating, 143 reviews

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

AndreasRating, 5 stars2 months ago
Amazing experience thank you for everything
Guest favorite
Home in North Miami
4.94 out of 5 average rating, 141 reviews

Bright and fun heated POOL home - 5 bedrooms

KarinRating, 5 stars1 week ago
The house is beautifully renovated in a style that reflects the area. The outdoor area is relaxing and fun for families.
Guest favorite
Home in Hollywood
4.92 out of 5 average rating, 153 reviews

Hard Rock Villa - House With Pool & Selfie Walls

DavyRating, 5 stars2 months 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, 142 reviews

Urban Oasis With Pool at West Wynwood/Allapattah

BaijayantiRating, 5 stars2 weeks ago
We had a great time at this place. Ezequiel was a great host. He was very responsive to our queries.
Guest favorite
Home in Miami
5 out of 5 average rating, 22 reviews

Miami Oasis: Charming home with private pool

CooperRating, 5 stars1 month ago
Great place and location. Very clean and comfortable. Great communication from the host and the check in/out was seamless. Walkable to starbucks, food, and grocery stores.

Condo rentals with a pool

Superhost
Condo in Sunny Isles Beach
4.92 out of 5 average rating, 12 reviews

le cartier sunny isles ocean paradise

SoledadRating, 5 stars2 weeks ago
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!!
Guest favorite
Condo in Brickell Business District
4.89 out of 5 average rating, 196 reviews

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

AnalucRating, 5 stars4 weeks ago
The apartment has a breathtaking view, it is very comfortable and well located, easy to get transportation. Also Kleber and Hannah were very kind, responsible and helpful.
Superhost
Condo in Sunny Isles Beach
4.89 out of 5 average rating, 105 reviews

Golden Bay Club Beautiful Condo! -STR-02901.

SarahRating, 5 stars1 month ago
Nice spacious condo walking distance to the beach in Sunny Isles. Responsive host and no issues throughout the stay.
Guest favorite
Condo in Miami
4.89 out of 5 average rating, 18 reviews

Modern Spacious 2 Bed In Aventura/ FREE Parking

MichaelRating, 5 stars6 days ago
Place was spotless and we will stay again! Dmitry is a great host!
Superhost
Condo in South Beach
5 out of 5 average rating, 4 reviews

SoBe condo with amazing views

DanaRating, 5 stars7 months ago
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!
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 stars6 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
4.85 out of 5 average rating, 34 reviews

Ocean Breeze

LouAnnRating, 5 stars1 week ago
Lovely little place and a great value for the price, while being located near everything in the very upscale neighborhood of beautiful Key Biscayne. I was traveling solo and always felt safe out and about, even at night. The accommodations were cozy and clean with warm decorations and artwork. Comfortable bed, great shower. Big closet with plenty of linens. Nice ceiling fans with good A/C. Beach chairs, beach towels, umbrella, beach toys and books too. The private patio was relaxing and peaceful. The public beach and two grocery stores are within walking distance. There is a golf cart rental place also within walking distance and they are handy to rent for visiting the beautiful beaches, sunsets, and restaurants at the Bill Baggs Cape Florida State Park. Miami-Dade county offers great Ecoadventures and I enjoyed kayaking. Ginny is a very friendly and responsive host. Her communication is prompt and she works to accommodate you regarding anything you need. Highly recommend it!
Guest favorite
Condo in Sunny Isles Beach
5 out of 5 average rating, 27 reviews

Oceanfront Remodeled Beautiful Condo

RoseanneRating, 5 stars1 week ago
Beautiful condo, immaculate and charming interior. Loved the decor, very inviting and comfortable. Much larger than I expected. Igor, our host, was extremely helpful and responsive. Loved our visit. Sorry to leave, hope to return next year. Thank you Igor for making our stay in Sunny Isles memorable.

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

    1.5K 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

Destinations to explore