Vacation rentals with a pool in Windsor Hills

Find and book unique homes with a pool on Airbnb

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 ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 1,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Windsor Hills vacation rentals include wi-fi 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!

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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Guest favorite
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 favorite
A large private pool is surrounded by lush tropical plants and a spacious deck area. A shaded cabana offers a comfortable retreat nearby, with light filtering through the draped curtains, creating a refreshing outdoor environment.
Guesthouse in Reseda
4.99 out of 5 average rating, 769 reviews

Plant Lover's Paradise: Jacuzzi/Pool, 420 Welcome

A plant lover's paradise tucked into a private backyard studio guesthouse, your own escape w/ a cal king bed, large pool, hot tub, cabana, and massage chair, not shared, all yours to enjoy! Surrounded by tropical fruit trees, an organic garden, and an aquaponics system, a true botanical hidden oasis. Cannabis-friendly (outdoors only). Mention "420" for complimentary organically grown pre-rolls (subject to availability). Max 2 guests. Please confirm you've reviewed the house rules when booking.

Guest favorite
The exterior view presents a charming villa enveloped in greenery, with a sprawling front lawn and well-maintained flower beds. The home showcases an inviting facade highlighted by large windows, flanked by a two-car garage on a patterned driveway, all set against a vibrant sunset sky.
Home in Studio City
4.9 out of 5 average rating, 137 reviews

Luxurious villa King Beds Pool & Spa

Unique, stylish, and luxe Villa located in the heart of Studio city Easy access to Westside, shopping & dining on the blvd. Views! Special features include a sparkling heated pool and spa, indoor and outdoor firepit, chef's kitchen, and spacious bedrooms with designer bathrooms. Hardwood Floors and recessed lighting as well as our seamless check-in via personalized key code. There is always someone available to help with questions to make your stay an effortless and magical experience!

Guest favorite
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 South LA
4.8 out of 5 average rating, 256 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.

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 favorite
A welcoming living room showcases original hardwood floors and vintage Mexican tiles. Dutch doors open into the space, which features a Danish rosewood sofa, two wooden chairs, and a coffee table adorned with books. Natural light filters through the windows, highlighting the rustic decor.
Home in Glendale
4.97 out of 5 average rating, 322 reviews

Pool and Historical Swiss Chalet in Los Angeles

The Swiss Chalet is a historic home featuring original architecture and design. The Chalet also features lush gardens, a pool, and a hot tub on the private upper terrace. Enjoy the view of the mountains, bask in the sun by the pool, take in the sunset over a glass of wine from the veranda, and stargaze from the hot tub nestled between majestic pines and picturesque Californian oaks. Please note: no kitchen, and no parties. Glendale Home-Sharing License: HS-003915-2025

Top guest favorite
The charming cottage is framed by well-maintained gardens, showcasing warm outdoor lighting that enhances its welcoming entrance. A spacious lawn stretches in front, bordered by vibrant greenery and flowering plants, creating a tranquil outdoor setting.
Cottage in Pasadena
4.97 out of 5 average rating, 350 reviews

Gracious Historical Cottage on Tranquil Estate

Welcome to the historic Markham Estate Manor, built in 1897 and located in the heart of Pasadena. Nestled just off Orange Grove Boulevard —famously known as Millionaire’s Row and along the iconic Rose Parade route—our property is central to Old Town Pasadena, the Huntington Library, the Gamble House, and offers convenient access to Southern California attractions. The property includes the Main House, where I reside, and a charming, stand-alone cottage for guests.

Top guest favorite
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.

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 Central LA
4.98 out of 5 average rating, 283 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 favorite
Home in Mid - Wilshire
4.92 out of 5 average rating, 348 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 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, 199 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 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 South LA
4.96 out of 5 average rating, 213 reviews

Classic LA Mediterranean w/ City Views

Welcome to Grandma’s Castle! This is one of the historic homes in the neighborhood. My partner and I purchased our home in 2018 and we have been restoring her, little by little. It is a big task, but a rewarding one. One notable fact about the home is that Mike Love, of the Beach Boys, lived here as a teenager. I love sharing my home and meeting people from all over the world. I hope to meet you too.

Popular amenities for Windsor Hills rentals with a pool