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 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
4.88 out of 5 average rating, 160 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 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, 110 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.

Guest favourite
The studio features a spacious bed covered with a light quilt, positioned next to a nightstand. An extendable couch is draped with a gray cover, situated across from a television on a white media console. Natural light illuminates the room through two windows.
Guesthouse in Venice
4.91 out of 5 average rating, 422 reviews

Venice Beach Gem – Private Entry & Parking

Bright & Spacious Studio – 5 Minutes to the Beach! 🌊☀️ Escape to this beautiful, sun-filled studio with private entrance & parking, just a 5-minute bike ride to the beach! This 400 sq. ft. retreat boasts high ceilings, 6 windows for amazing natural light, and all the comforts of home— a private bathroom, AC. In the heart of Venice, you're just a short walk to Abbot Kinney, where you’ll find LA’s best coffee, restaurants ,boutiques. Work/leisure, this is perfect for your LA adventure!

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.
Guesthouse in Los Angeles
4.98 out of 5 average rating, 154 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, 276 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.
Guesthouse in Carthay Square
4.99 out of 5 average rating, 278 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
Home in Mid - Wilshire
4.92 out of 5 average rating, 328 reviews

Pool Oasis in Vintage Craftsman House

Unwind on the pool terrace of this 1919 Craftsman cottage. Soak in the hot tub or gather at the fire pit by night. Watch movies with surround sound. The renovated, open interior features hardwood floors and a flowing open-concept living space. NOTE: No parties, events, filming. No exceptions. This house is just for quiet enjoyment while you visit LA. Early check-in / late check-out generally not available due to cleaning protocol.

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.

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, 227 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.

Top 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, 272 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 favourite
A nighttime view of the Downtown Los Angeles skyline, featuring illuminated skyscrapers with varying architectural designs. The city lights create a vibrant mosaic against the dark sky, highlighting the impressive height of the buildings and the organized layout of the streets below.
Condo in Downtown Los Angeles
4.98 out of 5 average rating, 109 reviews

DTLA Skyscraper With City Views

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 absolutely stunning views of downtown, watch the organized chaos from high above in our tranquil condo.

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.
Guesthouse in Venice
4.96 out of 5 average rating, 1,150 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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Avg. price$330 NZD$319 NZD$331 NZD$321 NZD$317 NZD$319 NZD$335 NZD$338 NZD$308 NZD$347 NZD$328 NZD$322 NZD
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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 $71 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Westchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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