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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Top guest favorite
The images showcase a spacious living area featuring a comfortable brown leather sectional sofa, a circular wooden coffee table with a potted plant, and high wood-beamed ceilings. A glimpse of the outdoor pool area is seen, with a crystal-clear blue pool and surrounding patio, highlighting relaxation and playful outdoor activities.
Home in Westchester
4.99 out of 5 average rating, 106 reviews

World Cup Retreat • Private Pool • 3BR • Near LAX

🌍 Welcome to Your 2026 World Cup Home Base in LA Experience the FIFA World Cup from a spacious, private 3-bd / 2-ba home near SoFi Stadium in Westchester (90045). It features a spacious eat-in kitchen with an island overlooking a large living room. Outside you’ll find a fire pit, gas BBQ and show stopping saltwater pool that can be heated. Whether you’re here to support your team, attend multiple games, or host friends between games, this home offers the space, comfort, and location you seek.

Top guest favorite
A spacious studio features a cozy queen-sized bed positioned near a light-filled window. A comfortable sofa and armchairs surround a modern coffee table, providing seating options. Wood flooring complements the contemporary furnishings, while shelves display a collection of books and art pieces.
Guesthouse in Highland Park
4.97 out of 5 average rating, 605 reviews

Modern Guesthouse in Highland Park: Pool & Parking

Relax in this serene, private Los Angeles retreat in Highland Park, set on a large, gated property near Pasadena and surrounded by a Mediterranean garden under the California sun. This beautifully designed, recently constructed modern guest studio is a separate, stand-alone structure from the primary residence, offering access to a shared swimming pool and dedicated off-street parking on a secure property. A curated original collection of art and photography books is available for guest use.

Superhost
A rope swing hangs near large windows, offering views of Downtown Los Angeles and its skyline. Bright natural light floods the room, highlighting a cozy seating area and vibrant green plants along the edges of the space.
Loft in Downtown Los Angeles
4.92 out of 5 average rating, 111 reviews

Golden Hour Loft DTLA w/ free parking and hot tub!

Welcome to your oasis in the heart of Downtown LA! Located in the groovy Theater District, Golden Hour Loft is the perfect way to experience Los Angeles — from your fairytale swing high above the skyline. Hot tub, pool, cabanas, gym, record player, board games & coffee bar: this is your home base to live your DTLA dream. Our 97 Walk Score means you’re only steps from the trendiest shops, eats & drinks in the city. And did we mention free parking? All of Los Angeles is at your fingertips.

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, 283 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 favorite
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 favorite
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, 165 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 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, 221 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 favorite
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, 233 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 favorite
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
4.91 out of 5 average rating, 275 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, 1,158 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, 127 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!

Guest favorite
A spacious sleeping area featuring a large bed with a yellow patterned blanket. The walls are painted in a soft green, complemented by a framed artwork above the bed. A sitting area is present, with a lamp and contemporary chair, and natural light enters through a window covered by sheer curtains.
Guesthouse in El Sereno
4.97 out of 5 average rating, 549 reviews

Urban Retreat

Detached guest house nestled on a hilltop within a completely private compound. Our home is our sanctuary, a place to escape the hustle and bustle of the city. Yet, we are right in the middle of the city! Home Sharing Registration Number: HSR19-000268

Popular amenities for Westchester rentals with a pool

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$38,733 GYDG$37,477 GYDG$38,942 GYDG$37,686 GYDG$37,267 GYDG$37,477 GYDG$39,361 GYDG$39,780 GYDG$36,221 GYDG$40,827 GYDG$38,524 GYDG$37,895 GYD
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Quick stats about vacation rentals with a pool in Westchester

  • Total vacation rentals

    Explore 230 vacation rentals in Westchester

  • Nightly prices starting at

    Westchester vacation rentals start at G$8,375 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,640 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Westchester vacation rentals include wi-fi 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