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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 serene outdoor space features a beautifully designed lap pool adjacent to a spa, set against a backdrop of a brick guest house. Lush green grass surrounds the area, creating a peaceful environment. French doors provide access to the interior, enhancing the inviting atmosphere.
Guest house in Glassell Park
4.93 out of 5 average rating, 550 reviews

Designer’s Dream Oasis with Lap Pool & Hot Tub

Relax in the oasis of this wholly remodeled 1920s Craftsman-style guest house, dubbed the Boat House due to its proximity to the LA River. Impeccably designed brick industrial with intimate light-filled interiors, the Boat House has its own entrance and shares a large yard, fire pit, lap pool, and hot tub with the main house 50 feet away. NOTE: Euro-style kitchen includes refrigerator, toaster oven, portable electric cooktop (two burners), microwave, electric kettle for making coffee, teas, pots, pans, plates, etc. Street parking is usually never an issue. Please read the online manual. Modern, comfortable, loft-like space in hip East LA hood, Glassell Park! (FYI, it's not a real a boat house), but a unique 1920s brick building on a quiet residential street. We call it the "Boat House" because of close proximity to the LA River. The building has polished concrete floors, wood beams, mid-century design, custom copper faucets, custom OSB cabinetry & one-of-a-kind art & furnishings. There's a cozy fire-pit area right outside the door to enjoy as well as a pool, spa and fruit trees. NO FILM SHOOTS ALLOWED. PLEASE DON'T INQUIRE UNLESS PLANNING TO PAY 4X THE RATE. We lovingly designed, carefully curated and restored the guest house. We so appreciate you treading kindly with respect to the furnishings and items that share the space - (ie, please don't take the vintage pottery outdoors), typewriter (just for show), artwork, collection of books & furniture. PLEASE, NO WET TOWELS or bathing suits hung anywhere but on the hooks provided or in bathroom. There are blinds in the rooms for your privacy. The building is historic so thank you for being mindful and not putting anything other than Toilet paper in the toilet. Thank you!! The guest house shares a spacious back yard with the main house where we live. The backyard has fruit trees & a cozy fire pit. You have a private entry through a side gate. Ample street parking. We're an active family with two small kids. We live in the main house on site. We also have a chill labradoodle dog named Mel & two outdoor kitties. My hubby and I are both documentary filmmakers & have travelled extensively. We love hosting folks from all over so please say hello during your stay! We've provided blinds in the guest house and respect your privacy (we won't be too loud too early). We share our backyard with you and love to enjoy the outdoor space. We swim often, BBQ and use the firepit. Feel free to join us! (if the pool safety net is in place, please don't try and remove it yourself, thx). Please let us know if you'd like to use the pool and/or spa. The pool is heated by the sun but the spa can be quickly heated for your enjoyment. Just ask! Occasionally, we host friends, brunch & parties. Again, feel free to join in! We're easy going like that. Someone is usually on site to help with your needs or just a phone call or text away. Enjoy your stay! The guest house is located behind the main house on a quiet street, close to great coffee shops and restaurants. East LA is both hip and full of colorful diversity. The location is convenient to Silverlake, Los Feliz, Griffith Park, and Downtown. Ride sharing works great! We recommend it - Lyft or Uber. Also, various metro lines are located a couple miles away. And, Enterprise car rental has locations nearby. We're conveniently located near the 5 and 210 freeways. We live in a very ethnically diverse neighborhood. A few times a year some of our neighbors have parties: Quinceaneras, birthdays, Tomborazo bands, etc. We've never found them to be intrusive & rather enjoy the festive music!

Top guest favourite
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.
Guest house in Highland Park
4.97 out of 5 average rating, 611 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.

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
4.98 out of 5 average rating, 281 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.

Guest favourite
A spacious living area features large windows, allowing ample natural light to fill the space. A comfortable gray couch sits in the center, facing a large TV and audio equipment. Decorative plants and shelves with musical instruments add character to the room.
Apartment in Downtown Los Angeles
4.95 out of 5 average rating, 103 reviews

The Lofts: Rooftop Pool & Spa, Free Parking, DTLA

Enjoy this music-themed DTLA Loft with free parking, a very rare find in an amazing location. Very family friendly, close to sites, quiet, and respectful neighbors. Very unique space! This unit has a living room, kitchen, bedroom and bath, Enjoy everything about Los Angeles from this amazing loft! PLEASE NOTE: The rooftop area, including the pool and hot tub, is currently CLOSED for construction and will remain UNAVAILABLE until September 29, 2025.

Guest favourite
A comfortable seating area features a plush sofa adorned with yellow and blue decorative pillows. The backdrop is a deep green wall displaying an array of framed artwork. A round mirror reflects light from a nearby window, and a bookshelf alongside adds a touch of charm.
Loft in Downtown Los Angeles
4.94 out of 5 average rating, 413 reviews

Angel City Historic Loft - Dtla Views & Urban Retro Design

Read House Rules and neighborhood descriptions BEFORE booking. By booking you accept all house rules! Come enjoy the beautiful views & relax in this 10th floor 1920s Beaux-Arts loft located in the Historic Core. The industrial past of this renovated space is still present in its high concrete ceilings and floors. Per building security rules, guest must provide government ID to host and/or guard once booked.

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
4.91 out of 5 average rating, 286 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!

Guest favourite
A rooftop pool is surrounded by lounge chairs, offering views of the city skyline. The pool's clear water reflects the buildings, and glass railings provide an unobstructed view of the surroundings. The area is well-lit and designed for relaxation.
Flat in Downtown Los Angeles
4.93 out of 5 average rating, 234 reviews

J-Boho Chic Condo-Free Parking-Rooftop Pool & Spa

Beautiful 1 Bedroom condo on historical Broadway Blvd. Right next to Ace Hotel, this building used to be the largest costume shop in the world. Actor's like Charlie Chaplin used to come and pick up their attire here. 20ft+ceilings & views of the sunsets and city lights have you feeling the vibes during the evening hours. Includes TV and fast WIFI.

Top guest favourite
Apartment in Downtown Los Angeles
4.99 out of 5 average rating, 136 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.
Guest house in Venice
4.96 out of 5 average rating, 1,176 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 favourite
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, 132 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!

Top guest favourite
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.
Guest house in El Sereno
4.97 out of 5 average rating, 556 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

Guest favourite
The image captures a serene pool area surrounded by lush greenery and wooden decking. Tall palm trees and bamboo create a tranquil setting, while a vibrant wall adds a pop of color. Comfortable lounge chairs are placed along the poolside.
Guest house in Venice
4.98 out of 5 average rating, 192 reviews

Tropical Oasis with Pool and Jacuzzi in Venice

The guest house is situated in an extensive backyard behind the main house. Enjoy the serenity of your patio overlooking the freshwater Pool and Jacuzzi - yours to use exclusively during your stay. Secured parking on the premises.

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 250 holiday rentals in Westchester

  • Nightly prices starting at

    Westchester holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wifi availability

    250 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