Vacation rentals with a pool in Windsor Hills

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windsor Hills

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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.

Superhost
A bright living area features large windows dressed with dark curtains, allowing natural light to fill the space. Elegant light fixtures hang from the ceiling. A plush sectional sofa is arranged around a glass coffee table, while a modern dining table and chairs are positioned nearby.
Condo in Downtown Los Angeles
4.85 out of 5 average rating, 149 reviews

DTLA Elegance & Style (1 bdrm, Free Parking, Pool)

For your next trip to LA, go in the style you deserve with our elegant and spacious condo in the heart of DTLA. Every inch of our home has been meticulously designed to give guests the kind of luxury they can't find elsewhere. From our 12 ft ceilings to our incredibly comfortable canopy bed, our goal is to make it hard for you to want to leave the space and explore everything LA has to offer, such as being walking distance to the LA Convention Center and Crypto Arena. Free Parking Included!

Top guest favourite
A pool area features six lounge chairs arranged beside a clear pool, reflecting the sky. A shaded dining table with colorful chairs sits nearby, offering a place to enjoy meals. Lush greenery and distant hills enhance the serene view under a softly lit, cloudy sky.
Guest suite in View Park-Windsor Hills
4.96 out of 5 average rating, 199 reviews

Classic LA Mediterranean w/ City Views

I love being a host! My partner and I purchased our home in 2018 and are restoring her little by little. This is one of the historic homes in the neighborhood and we are doing our best to bring her back to life. One interesting fact about the home, Mike Love, of the Beach Boys, lived here as a teenager and wrote a song about the property that was recorded on the Holland album. I am stunned by the views across the city to downtown LA every time I see them. Hope you will stay with us!

Guest favourite
A spacious backyard features a large swimming pool surrounded by lush greenery and patio furniture. A wooden deck offers comfortable seating with colorful cushions, while a covered seating area and landscaped paths lead to the guest house in the background.
Home in Miracle Mile
4.95 out of 5 average rating, 153 reviews

Amazing little paradise in the middle of LA

Experience a beautifully private guest house 400 SF with modern ful Bathroom complete with a luxurious California king bed, a cozy sofa, and a large flat-screen TV. Large refrigerator, a microwave, a coffee maker, and an espresso machine Take a short walk to Museum Row and The Grove, 20-minute walk to Beverly Hills. You'll also meet our friendly Milow golden retriever, who adores being petted and enjoys staying indoors. the perfect retreat, complete with a dedicated parking space! 🏡

Guest favourite
A cozy bedroom features a spacious bed with light-colored linens and several decorative pillows. A contrasting patterned throw lies at the foot of the bed. A mirrored wall adds depth, while a dresser provides additional storage.
Guesthouse in View Park-Windsor Hills
4.81 out of 5 average rating, 247 reviews

Cozy Pool House & Retreat - Los Angeles,CA View Pk

This is a recently renovated pool house is centrally located in the scenic View Park neighborhood of Los Angeles, CA, near LAX. This beautifully furnished one bedroom suite designed for your pleasure and PRIVATE relaxation. All are welcome! This pool house accommodates four (4) people. The suite includes (1) bedroom and bathroom, a common living area with a sofa bed, 60" TV, a kitchenette and a washer/dryer unit. Guest can also enjoy the PRIVATE pool, hot tub, and a beautiful deck area.

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
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
The exterior view of the studio cottage showcases a welcoming entrance surrounded by greenery. Two blue chairs and a small table are positioned in a sandy area, with garden features including foliage and decorative plants. Natural light filters through trees, creating a serene setting.
Cottage in Highland Park
4.93 out of 5 average rating, 427 reviews

Studio Cottage

This is a small Studio cottage at the rear of my home. It's craftsmanesk in style with a partially open ceiling and a skylight. It's perfect for a couple or single person. There is a swimming pool but it's not heated, fine for swimming June to Oct depending on the weather, unless you are a polar bear. It's a 5 min walk to the MetroGold Line and a 10 min walk to new restaurants on Figueroa St. I have a fairly extensive cactus / succulent garden.

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
A modern pool area is featured, with a clear blue swimming pool surrounded by a spacious deck. Two lounge chairs are positioned under a striped umbrella. In the background, a two-story building is visible, flanked by lush greenery and a serene atmosphere.
Guesthouse in Highland Park
4.97 out of 5 average rating, 599 reviews

Private Modern Guesthouse with Pool, View & Garden

Relax in this serene retreat under the California sun, surrounded by a Mediterranean garden on a peaceful private lot. This beautifully designed modern guest studio is a separate structure from the primary family residence on a secure, gated property with a dedicated off-street parking space for guests. • Non-smoking Property • Only two Airbnb guests per stay • Shared Swimming Pool w/ Hosts

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, 208 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, 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.

Popular amenities for Windsor Hills rentals with a pool

Quick stats about vacation rentals with a pool in Windsor Hills

  • Total vacation rentals

    Explore 20 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at $71 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Windsor Hills vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.9 Average rating

    Windsor Hills stays are highly rated by guests—averaging 4.9 out of 5!