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.

0 of 0 items showing

1 of 3 pages

Guest favorite

A modern two-story house is surrounded by lush greenery, with large glass doors providing a view of the interior. A circular salted swimming pool, illuminated in a gentle turquoise, is placed adjacent to a spacious outdoor seating area.

Home in Los Angeles

4.89 out of 5 average rating, 158 reviews

Honeymoon House in Hollywood Hills

About 3 mins drive up to the hills from the Sunset Plaza. Nice modern looking vintage house. Not the brand new condition. Invisible from outside by trees surrounding the house. City view from the second floor. Salted swimming pool can be heated at 83F degree. (Need to let us know before arriving) About 2,200 sq house out of 6,000 sq land. Must take off the shoes inside the house. No parties, gatherings or pets allowed. No music or outdoor activities after 10pm by city law. Thank you.

Top guest favorite

An inviting backyard space features a crystal-clear pool surrounded by vibrant greenery. Two lounge chairs adorned with tropical patterns are positioned near the water, offering comfortable spots for relaxation. Potted plants add a touch of natural beauty, creating a serene outdoor atmosphere.

Guesthouse in Reseda

4.99 out of 5 average rating, 721 reviews

Plant Lover's Paradise: Jacuzzi/Pool, 420 Welcome

Unwind in our studio guesthouse, tucked away in a peaceful backyard retreat with a large private pool, cabana, massage chair, and hot tub. Immerse yourself in paradise, surrounded by tropical fruit trees, an organic garden, and an aquaponics system. Outdoor bliss awaits for 420 enthusiasts (outdoors only). Mention '420 friendly' while booking to receive a gift of our homegrown, pesticide-free cannabis. Max 2 guests, no exceptions. Kindly review our description and house rules before booking.

Superhost

Tiny home in Topanga

4.92 out of 5 average rating, 198 reviews

Topanga Canyon Oasis by Colby & Conrad

Be WOW-ed by nature's beauty on this superbly curated, effortlessly magnificent property at the edge of an enchanting forest. Plunge into the infinite pool & warm up in the spillover hot spa as you take in the pristine canyon view. Sip coffee under the oaks listening to the hum of birds & bees. Explore the winding paths thru the crystal forest & cactus garden. Enjoy concierge wellness services on-site. A perfect respite for any retreat. Join us to renew. Featured in Better Homes & Gardens.

Guest favorite

A rooftop pool area is seen overlooking the Downtown Los Angeles skyline at sunset. The pool is flanked by lounge chairs and green umbrellas, with the reflective water showcasing the vibrant colors of the evening sky.

Loft in Downtown Los Angeles

4.92 out of 5 average rating, 185 reviews

Deco Modern 1BR/1BA Loft in DTLA w Pool & Jacuzzi

➜ To ensure everyone's safety, the building has a thorough registration process, and unfortunately, I can't accept same-day bookings. All guests over 18 need to submit a clear photo of their Government Issued ID, at least 24 hours before check-in. ➜ Please be advised that convenient parking is available just across the street for only $10/day. If you'd like to use it, let us know ahead of time, so we can have the payment sorted and have the fob ready for you at the unit.

Top guest favorite

A serene pool area is featured, surrounded by lush greenery and wooden decking. The clear, still water of the pool reflects the sky, while a dark cover rests on a lounge area nearby. Natural stone pathways enhance the tranquil outdoor setting.

Guesthouse in Los Angeles

4.98 out of 5 average rating, 150 reviews

Private pool-side casita with stunning views!

This secluded, gated, lux retreat with stunning views sits on over 1 acre in a country-like setting with easy access to LA activities. Resort features include steam shower, filtered water, fire pit, pool, hammock, Alexa, 50” TV , hi-speed wi-fi, printer, desk, Nespresso coffee maker, BBQ w burner/pots/pans, remote controlled black out blinds, private patio, with luxury amenities and designer details. For reservations more than 3 months in advance, please inquire.

Top guest favorite

Double doors open to reveal serene outdoor views of lush greenery and rolling hills. A wooden deck surrounds a tranquil plunge pool, creating a seamless connection between indoor and outdoor spaces. Natural light floods the room, accentuating the inviting ambiance.

Bungalow in Topanga

4.97 out of 5 average rating, 262 reviews

Topanga Pool House

The Topanga Pool House is a resort like property located at the edge of the State Park, with canyon views & ocean breezes. The infrared sauna, cedar plunge pool, hot tub, outdoor bed and yoga deck provide an escape from the hustle of the city. Guests have said it's "as if you have a resort to yourselves" "spa like" "magical and healing" and that's the experience we strive to provide. We live in the upstairs unit but prioritize guest's privacy at all times.

Guest favorite

An outdoor area features a sparkling pool surrounded by comfortable lounge chairs, with an umbrella providing shade. The guesthouse, displaying a charming exterior with multiple windows, is seen in the background. A hot tub is adjacent, alongside a barbecue grill, adding to the relaxing atmosphere.

Guesthouse in Carthay Square

4.99 out of 5 average rating, 271 reviews

Luxurious Guesthouse w/ Pool & Spa in L.A.

Charming guesthouse with a beautiful pool and hot tub near Beverly Hills. Enjoy your own space, complete with a kitchen and living room, and a master suite upstairs. This two-story guest house is 1000 sq./ft. The Airbnb is centrally located with easy access to all that LA has to offer. Two blocks to Beverly Hills, walking distance to Museum Row, about one mile from the Grove and West Hollywood. This detached guest-house has its own entrance and easy access.

Top guest favorite

A refreshing pool is surrounded by lush greenery and potted plants, creating a serene outdoor space. A patio area is visible, with a barbecue grill and sunshade overhead. In the background, a garden area features a small seating area, enhancing the tranquil atmosphere.

Guest suite in Silver Lake

4.98 out of 5 average rating, 153 reviews

Oasis in the City

Come relax at your own oasis in the neighborhood of Silver Lake in Los Angeles. Perched on a hill, with stunning views, access to a pool, lots of outdoor space and beautiful gardens in which to relax, and easy walking distance to 60+ restaurants and bars, this house is the perfect retreat. Originally an artist's studio, the space is filled with art and books, making it the perfect place to relax and enjoy.

Top guest favorite

An expansive view showcases a city skyline at dusk, with a gradient of warm colors in the sky. Swimming pools are visible in the foreground, surrounded by lounge chairs. City lights begin to twinkle below, highlighting the urban landscape transitioning from day to night.

Tower in Downtown Los Angeles

4.97 out of 5 average rating, 193 reviews

Ocean View From DTLA Skyscraper

Experience Downtown Los Angeles from the top of its skyline. Whether you're in town for a convention, show, sporting event or weekend away, you'll love the luxurious amenities and incredible view this listing has to offer. With views from the Griffith Observatory in the north, to Long Beach to the south, take in the vast expanse of Los Angeles with views to the Pacific Ocean.

Guest favorite

A spacious outdoor area features a clear swimming pool surrounded by light-colored stone tiles. A built-in bar with high stools stands nearby, complemented by lush greenery and palm trees in the background. Power lines and a wall provide additional context to the scene.

Guest suite in View Park-Windsor Hills

4.9 out of 5 average rating, 261 reviews

Hasta La Vista w/Pool

Welcome to Historic View Park! Enjoy a private master suite on the first floor with its own entrance, bathroom, and shower. Relax with stunning views of Downtown LA and the Hollywood Sign, plus private walkway access to the pool. The suite is fully closed off from the main house for complete privacy. We’re a friendly family of three and look forward to hosting you!

Top guest favorite

A private pool area is surrounded by a stone patio and lush greenery. A covered outdoor cabaña is present near the pool, equipped with seating. Prominent blue and green planters adorn the pool edge, enhancing the relaxing atmosphere, while a well-maintained lawn provides additional outdoor space.

Guesthouse in Venice

4.96 out of 5 average rating, 1,139 reviews

Venice Beach Guest Studio with Pool and Hot Tub

You have a charming Spanish 1926 architecture pool house. It’s located in the back of my house with all of the amenities necessary to enjoy your stay. ***MUST LOVE DOGS: I have 1 small friendly dog that lives with me in my house in front, I will keep him inside for the most part while you are here, but he will be around.

Top guest favorite

A secluded outdoor area is bordered by high fencing, offering total privacy. A clear swimming pool is surrounded by lush tropical plants, complemented by comfortable lounge furniture on an expansive wooden deck. Natural light enhances the serene atmosphere of this inviting space.

Home in Mar Vista

4.99 out of 5 average rating, 119 reviews

Pool House Oasis Close to Venice & Marina

This newer 3 bed/2bath duplex style home is centrally located between Venice & Marina Del Rey. Walking distance to local restaurants, markets, shops, and bars and about 1.5 miles to the beach, 5 miles to the airport and 8 miles to Sofi stadium. The backyard pool and spa is exclusively for your use!