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Holiday 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 favourite
A private outdoor space features a small pool surrounded by paved areas and lush green grass. Two lounge chairs are positioned nearby, offering a comfortable spot for relaxation. The background is enhanced by lush greenery, creating a serene atmosphere.
Home in Hollywood Hills
4.89 out of 5 average rating, 596 reviews

Hollywood paradise studio in house,own entrance

Settle into historic Hollywood in our brand new house with owned entrance private room-studio with queen size bed and privet bathroom. Very quiet and relaxing area, like 5 star hotel. Close to Hollywood Walk of Fame, Hollywood Sign, Sunset Blvd, West Hollywood, Hollywood Bowl (just 0,4 miles), Beverly Hills, The Grove, The Americana at Brand, Paramount Studios, Universal studio, Paladium, Downtown Los Angeles,Emerson College, Pantages Theatre, Highland,Hollywood lake park,Jimmy Kimmel show live

Top guest favourite
A modern two-story house is framed by landscaped grass and low-maintenance plants. A large driveway leads to a garage with glass doors. The facade is highlighted by warm lighting, enhancing the architectural features, set against a colorful evening sky.
Home in Mid City
4.96 out of 5 average rating, 108 reviews

2 story Modern Villa open concept house pool/spa.

This modern residence boasts updated bathrooms and kitchen, abundant natural light, and expansive, unobstructed areas. It features balconies, decks, a pool, and a spa, as well as fireplaces in both the living room and the master bedroom. The house exudes a cheerful atmosphere with stylish finishes and furnishings, creating a welcoming space for families to enjoy quality time together or for couples and friends seeking a resort-style vacation. Security cameras at front, side and back of house.

Superhost
A spacious living area features a comfortable brown sofa with a circular table in front. Behind, a bed is positioned against the wall, adorned with light blue bedding. Shelves display a collection of books and framed photographs, complemented by soft lighting from wall fixtures.
Home in Los Angeles
4.93 out of 5 average rating, 404 reviews

Stunning View Hollywood Hills Guest House

Stunning View Guest House in a multi-million dollar Hollywood Hills neighborhood, located near the iconic Stahl House founded by architect Pierre Koenig. Bright, open floor plan designed for elegance and comfort. It comes with high ceilings, new modern furnitures . Spacious unit 1 Bedroom + large Living Room with additional sleeping area. You would love the breath taking 180 degree LA city skyline views from the patio. An external stair lead to guest house giving you full privacy.

Top guest favourite
An outdoor deck features two lounge chairs and two playful, bright green floaties beside a sparkling pool. Umbrellas provide shade, while a glass wall offers views of lush greenery and natural surroundings, creating an inviting and serene environment.
Guest house in Los Angeles
4.98 out of 5 average rating, 152 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 favourite
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, 275 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.

Top guest favourite
A serene outdoor area is highlighted by a vibrant blue pool and a hot tub, featuring two lounge chairs and an umbrella nearby. The space is surrounded by lush greenery and well-kept landscaping, with doors opening to the inviting interior of the guesthouse.
Guest house in Carthay Square
4.99 out of 5 average rating, 277 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 favourite
An outdoor dining area features a rugged wooden table surrounded by black chairs, illuminated by a large orb chandelier. The space overlooks city views under a twilight sky, showcasing distant hills and lights of the Silver Lake neighborhood.
Guest suite in Silver Lake
4.98 out of 5 average rating, 159 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.

Guest favourite
The rooftop area features a shimmering pool and a relaxing jacuzzi, both illuminated at night. City skyscrapers stand majestically in the background, creating a vibrant urban atmosphere enhanced by the warm glow of surrounding lights.
Flat in Downtown Los Angeles
4.98 out of 5 average rating, 133 reviews

Luxurious Cal King Bed Suite, Skyline View of DTLA

On Broadway! Located in the heart of DTLA, Adjacent Ace Hotel. This posh unit offers high rise views in the historic fashion district. At our King Bed Suite, you'll first arrive to a beautiful and bright, modernly decorated yet historic lobby, and be greeted by professional and smiling concierge who will allow access so you can enjoy the downtown views of Los Angeles in a luxurious private suite.

Top guest favourite
A modern living area is illuminated with soft, colorful lighting. A dark couch is arranged around a glass coffee table, featuring decorative items. Floor-to-ceiling windows showcase a panoramic view of the city skyline at night, highlighting the vibrant lights below.
Tower in Downtown Los Angeles
4.98 out of 5 average rating, 206 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.

Top guest favourite
An outdoor area features a pool surrounded by a spacious deck. Lounge chairs with orange cushions are arranged near the water. A stone barbecue area is located adjacent to the pool, with a backdrop of vibrant skies and palm trees, contributing to a relaxing ambiance.
Home in Sherman Oaks
4.99 out of 5 average rating, 226 reviews

MULHOLLAND HILLS RETREAT W/BEST VIEWS IN LA

LOCATION, LOCATION, LOCATION. This iconic property is situated on a highly coveted street in the Mulholland Corridor near Beverly Hills, Sherman oaks, and Bel Air. The architecture, walls of glass, open floor plan & indoor/outdoor flow celebrate the California lifestyle. This Beverly Ridge residence has an emphasis on clean lines, open spaces and inspired architecture.

Guest favourite
A landscaped front yard features various palm and tropical plants, creating a lush and inviting entrance. The structure showcases a two-story design with a balcony, surrounded by greenery and stone accents on the façade. A clear blue sky complements the scene.
Guest suite in View Park-Windsor Hills
4.9 out of 5 average rating, 270 reviews

Hasta La Vista with 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 favourite
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.
Guest house in Venice
4.96 out of 5 average rating, 1,147 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.

Popular amenities for Westchester rentals with a pool

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Quick stats about holiday rentals with a pool in Westchester

  • Total holiday rentals

    Explore 230 holiday rentals in Westchester

  • Nightly prices starting at

    Westchester holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 2,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    230 of Westchester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Westchester rentals

  • 4.7 Average rating

    Westchester stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Westchester’s top spots include Loyola Marymount University, Cinemark 18 and XD Los Angeles and Aviation/LAX Station