Vacation rentals with a pool in Westchester

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Westchester

  • Total vacation rentals

    Explore 260 vacation rentals in Westchester

  • Nightly prices starting at

    Westchester vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    260 of Westchester vacation 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

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 spacious living area is illuminated by natural light through large windows. The wooden vaulted ceiling adds warmth, while a comfortable sectional sofa with decorative pillows faces a wooden coffee table. A dining area and modern kitchen are visible in the background, enhancing the homey ambiance.
Home in Silver Lake
4.97 out of 5 average rating, 383 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 favourite
A spacious outdoor deck features a set of modern loungers set against a backdrop of vibrant sunset colors. The deck overlooks rolling hills and a serene landscape, with a dining area visible nearby, providing an inviting space for relaxation or outdoor meals.
Home in Sherman Oaks
4.99 out of 5 average rating, 266 reviews

Iconic Mulholland Hills Retreat Best Views in LA

LOCATION, LOCATION, LOCATION. California casual with real Hollywood Hills energy. Perched on one of Mulholland’s most coveted streets — moments from Beverly Hills, Bel Air & Sherman Oaks — this private Beverly Ridge home is all about the view and the vibe. Walls of glass, open flow, canyon mornings, pool days, hot tub nights, and a screening room for movie nights. Not sterile or generic — warm, cinematic, unforgettable. Eight years of five-star hosting. A warm, soulful stay with cool LA energy.

Top guest favourite
A serene back garden features a heated pool adorned with a large pink flamingo float. A cozy fire pit is positioned nearby on a tiled patio, surrounded by decorative potted plants and colorful lighting, offering a relaxed atmosphere for outdoor gatherings.
Home in Los Angeles
4.96 out of 5 average rating, 299 reviews

Mermaid Manor* Colorful Cozy Coastal Gem

Safe, family-friendly- 9 miles to So FI stadium/Kia forum Relaxed, homey vibe-central AC/heat. Cozy fireplace, Stocked kitchen Comfy Beds Two TV's w/ streaming/fast WIFI Driveway Parking Tropical Garden - Dining area, BBQ, fire pit, loungers & shower. Solar-heated Pool (weather permitting) 4 Bikes/locks/Beach goods -Restaurants, Park & store walking distance. All spaces are fully private to you. Host lives on property but respects privacy-Reviews say it all. Outdoor 420-friendly

Guest favourite
An outdoor dining space features a round table surrounded by four cushioned chairs under a large umbrella. Lush tropical plants frame the area, and a serene saltwater pool is visible nearby, reflecting the clear blue sky.
Home in Westchester
4.86 out of 5 average rating, 159 reviews

Sunny House minutes from the beach!

This vacation paradise is centrally located—just 3 miles from SoFi Stadium, 3 miles from the beach, 1 mile from Culver City, and 3 miles from Los Angeles International Airport. Enjoy our sunny home with 3 bedrooms, 2 bathrooms, a fireplace, a gourmet kitchen, and a saltwater pool. World Cup tip: Getting to and from SoFi Stadium is easy. Take a Lyft to within about ¼ mile of the stadium and walk the rest. After the event, walk about ½ mile before requesting a pickup for a quicker departure.

Superhost
A modern kitchen features an island with a sleek countertop, a stainless steel stove, and ample cabinetry. The open layout connects to a dining area and a well-lit living space, with large windows providing a view of the outdoor swimming pool.
Home in Gardena
4.78 out of 5 average rating, 393 reviews

Blue White House

My beautifully renovated, freshly remodeled, contemporary house will satisfy you to the fullest!! The property is located in a charming city of Gardena, in the quiet family oriented, village like neighborhood. This comfortable, modern home is perfectly located just 15 minutes from LAX, 15-20 minutes away from Manhattan Beach, Hermosa Beach, 25 min. from gorgeous cliffs of Palos Verdes, and 25 min from downtown LA! Knot's, Soak City and Disneyland are just a short drive away!

Top guest favourite
Guesthouse in Hollywood Hills
4.98 out of 5 average rating, 178 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
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, 131 reviews

Chic Family Home: Pool, Firepit, Prime Location

Welcome to our serene and stylish family retreat, an oasis of comfort and elegance nestled in the heart of Los Angeles. Conveniently located only minutes to LAX & beaches, this spacious 3BR/2BA home is central to world-class amenities, shopping, and restaurants. It features a brand new spacious eat-in kitchen with an island overlooking a large living room. Outside you’ll find a fire pit, a gas BBQ and a show stopping saltwater pool that can be heated.

Superhost
Tiny homes in Topanga
4.89 out of 5 average rating, 258 reviews

Topanga Canyon Loft | Private Pool + Hot Tub | C&C

Tucked deep into Topanga Canyon's Fernwood arts enclave, this architectural tiny home for two pairs canyon seclusion with genuine luxury — a private infinity pool and steaming hot tub frame sweeping state park views from the wrap-around deck. Lofted queen bed beneath a vaulted ceiling, full kitchen, BBQ grill, and direct access to hiking trails in Topanga State Park. Just 15 minutes to the beaches of Malibu. 0BR/1BA, sleeps 2 Hosted by Colby & Conrad.

Guest favourite
Apartment in Marina del Rey
4.9 out of 5 average rating, 138 reviews

Clean & Spacious Marina 2BR w/Parking

Welcome to our bright, family & pet-friendly Marina retreat 💛 Comfortably sleeps up to 7 guests — perfect for kids & well-behaved pets. 2 parking spots included 7 ft garage clearance. Enjoy pool, jacuzzi & gym access. Fast WiFi & easy self check-in. Exterior video doorbell at entry for added security. Spotless, thoughtfully prepared, and designed for a relaxing stay.☀️☀️☀️☀️☀️

Guest favourite
Villa in Beverly Grove
4.86 out of 5 average rating, 301 reviews

Modern Moroccan Pool Paradise near WEHO/Bev Center

The house is in the heart of all the action of West Hollywood and the Beverly Center. You can walk to the heart of WEHO, Beverly Center, The Grove, Cedars Sinai Hospital and all of the nicest restaurants along Beverly, 3rd Street and La Cienega. Almost 3,000 s.f. on a corner lot with complete privacy. Minutes by car to Beverly Hills, Century City and the Hollywood Hills.

Guest favourite
Condo in Downtown Los Angeles
4.99 out of 5 average rating, 178 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
4.97 out of 5 average rating, 1,220 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