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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 €44 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
Bungalow in West Hollywood
4.87 out of 5 average rating, 540 reviews

Fab. Celebrity Area Guesthouse, Amazing View/Pool

One-of-a-kind guesthouse wing with vintage 40’s vibe. Million $ views from every room. See video tour, google sydsfabulousguesthouse17 before booking. Hot celebrity hillside area is walking distance to great eateries, entertainment and shopping. Washer/Dryer in garage. Pool warm Mid June-October. You’re free to hang there. Property runs on 100% solar. EV charger available. Free 24 hour street parking. No tobacco smokers (weed ok outside). See House Rules. This is an amazing upscale property!

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, 138 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
The garden area features well-maintained grass, with lounge chairs positioned on one side. A patio table and chairs are visible under a canopy, offering a shaded dining space. The house background includes a balcony, with strings of light enhancing the tranquil outdoor setting.
Home in Hancock Park
4.86 out of 5 average rating, 119 reviews

3600 sq foot Luxury Spanish Pool Mansion

Luxury Living ,1925 Spanish Mediterranean LA pool home awaits you in centrally located Hancock Park.3600 sft home features custom modern chef's kitchen, Timothy Oulton dining room seats 10 , pool table, high quality linens with memory-foam beds .Stunning marble bathrooms, lovely olive tree lined yard with pool and heated spa. Outdoor seating areas and BBQ. Central to DTLA, Koreatown, Larchmont ,Hollywood, Santa Monica, The Grove , Beverly Hills. Central luxury. You will love our place.

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!

Guest favorite
The living area features large windows allowing natural light to fill the space, showcasing views of the city skyline. A comfortable sofa is complemented by two leather chairs. Green plants and decorative elements provide a touch of warmth, while a coffee table holds stacked books.
Loft in Downtown Los Angeles
4.91 out of 5 average rating, 246 reviews

Deco Modern 1BR/1BA Loft in DTLA with Pool & Jacuzzi

➜ To ensure everyone's safety, the building has a thorough registration process, and unfortunately, I can't accept same-day bookings. All guests over 18 need to submit a clear photo of their Government Issued ID, at least 24 hours before check-in. ➜ Please be advised that convenient parking is available just across the street for only $20/day. If you'd like to use it, let us know ahead of time, so we can have the payment sorted and have the fob ready for you at the unit.

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
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 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, 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.

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
4.99 out of 5 average rating, 200 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, 214 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.

Top guest favorite
The rooftop area features a shimmering pool and a relaxing jacuzzi, both illuminated at night. City skyscrapers stand majestically in the background, creating a vibrant urban atmosphere enhanced by the warm glow of surrounding lights.
Apartment in Downtown Los Angeles
4.98 out of 5 average rating, 162 reviews

Luxurious Cal King Bed Suite, Skyline View of DTLA

On Broadway! Located in the heart of DTLA, Adjacent Ace Hotel. This posh unit offers high rise views in the historic fashion district. At our King Bed Suite, you'll first arrive to a beautiful and bright, modernly decorated yet historic lobby, and be greeted by professional and smiling concierge who will allow access so you can enjoy the downtown views of Los Angeles in a luxurious private suite.

Popular amenities for Windsor Hills rentals with a pool