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.

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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.

Guest favorite

Home in Silver Lake

4.97 out of 5 average rating, 345 reviews

The Paradise Hot-Tub Treehouse

Rejuvenate and play the piano in a secluded hot tub (& cold plunge!) under the stars, surrounded by tropical plants & fruit trees, with Big-Sur-style luxury hidden in the heart of Silverlake. On this quiet cul-de-sac, you may forget you're just a short walk to the best cafes & restaurants of Silverlake. The house boasts two private view decks, a desert & citrus garden, a pond, a fire pit, & a detached meditation/work room. Featured as one of 12 "dream homes" for rent in Los Angeles Magazine!

Top guest favorite

A serene outdoor space features a swimmer's pool with clear blue water, complemented by a circular spa surrounded by low decorative walls. Lounge chairs in bright orange offer seating beside the pool, while shaded areas and greenery create a peaceful atmosphere.

Guest suite in Hollywood Hills

4.99 out of 5 average rating, 187 reviews

Private Chic Guest Suite Beachwood Canyon Pool/Spa

Unwind in your own private tropical courtyard at this gated zen haven in peaceful Beachwood Canyon. Minutes from The Hollywood Bowl, Walk of Fame and Universal Studios. Walk to the famous Beachwood Cafe for your morning coffee. Enjoy your own 380 sq. foot Guest Suite with a private 700 sq. foot patio with sofa, fire pit & patio table. Take a dip in the swimmer's pool or luxuriate in the gorgeous 10 jet Mediterranean tiled spa. 2 TV's w/ free Netflix, Hulu, HBO Max and tons of street parking.

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, 148 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, 261 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

A serene swimming pool is framed by lush greenery, with a modern two-story guest house visible in the background. Soft lighting highlights the pool area, enhancing the peaceful ambiance of the outdoor space as evening approaches.

Guesthouse in Highland Park

4.97 out of 5 average rating, 593 reviews

Private Modern Guesthouse with Pool, View & Garden

Relax in this serene retreat under the California sun, surrounded by a Mediterranean garden on a peaceful private lot. This beautifully designed modern guest studio is a separate structure from the primary family residence on a secure, gated property with a dedicated off-street parking space for guests. • Non-smoking Property • Only two Airbnb guests per stay • Shared Swimming Pool w/ Hosts

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, 192 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 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, 182 reviews

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

Note: The roof deck, including the pool, gym, and all walkways, will be closed for maintenance from September 8 to 29th. ➜ 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.

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, 258 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, 1,137 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.