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Holiday 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 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, 359 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
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, 108 reviews

World Cup Retreat • Private Pool • 3BR • Near LAX

🌍 Welcome to Your 2026 World Cup Home Base in LA Experience the FIFA World Cup from a spacious, private 3-bd / 2-ba home near SoFi Stadium in Westchester (90045). It features a spacious eat-in kitchen with an island overlooking a large living room. Outside you’ll find a fire pit, gas BBQ and show stopping saltwater pool that can be heated. Whether you’re here to support your team, attend multiple games, or host friends between games, this home offers the space, comfort, and location you seek.

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.
Guesthouse in Highland Park
4.97 out of 5 average rating, 609 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.

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
4.94 out of 5 average rating, 161 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 3 minute 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 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, 202 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 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, 248 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 and living area are showcased, featuring sleek white cabinetry and stainless steel appliances. A curved, soft gray couch is positioned in the foreground, accompanied by a small side table. Natural light filters through large windows with sheer blinds.
Apartment in Vernon
4.92 out of 5 average rating, 125 reviews

LA Getaway (DTLA)| City View

Enjoy this stunning modern 1 bed/1 bath luxury apartment located in the heart of DTLA. This stylish apartment offers stunning views of the city, in unit washer/dryer, 4K TV, free parking, complimentary coffee, and many more amenities inside the complex. Located only 1 mile away from Crypto Arena, LA Live, & many other restaurants and attractions. 7 Miles away from Universal Studios. Additional amenities include: -Gym -Pool -FREE Parking Perfect for couples and small families!

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
4.98 out of 5 average rating, 280 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.
Condo in Downtown Los Angeles
4.95 out of 5 average rating, 101 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.

Superhost
Apartment in Downtown Los Angeles
4.95 out of 5 average rating, 134 reviews

Penthouse LA 1bed/1bath [VIEWS | SKY SUITE | POOL]

⭐️ PROPERTY IS LOCATED IN KOREATOWN LOS ANGELES ⭐️ SEE PICTURES FOR ACCURATE LOCATION THANK YOU! [ Penthouse Suite ] * Downtown Skyline View * Free Parking for 1 vehicle * Private en-suite bathroom * Brand new 14” memory foam King bed * Perfect location between Hollywood and Downtown LA (Crypto Arena) * Close to all major attractions Ideal for vacation or business travel. Enjoy the beautiful LA sunsets every day =) Travel in style!

Guest favourite
Home in Mid - Wilshire
4.91 out of 5 average rating, 333 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 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, 282 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!

Popular amenities for Windsor Hills rentals with a pool

Quick stats about holiday rentals with a pool in Windsor Hills

  • Total holiday rentals

    Explore 20 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at $83 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,450 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Windsor Hills holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Windsor Hills rentals

  • 4.9 Average rating

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