Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
Top guest favorite
Home in Encino
4.96 out of 5 average rating, 472 reviews

Keep Cool in the Poolside Shade at a Charming Encino House

Serve breakfast in a gazebo in a leafy backyard. Stride across flagstones and slip into a tranquil pool. Snooze in a hammock. Return indoors to cook in a family-style kitchen. Discover a spa-like room and relax in a hot bath, or daydream in a beautiful succulent filled garden. Gorgeous guest home South of Ventura Blvd with parklike grounds and pool. Heart of celebrity studded Encino. Attached to the main residence by a sealed hall, this 5-Star oasis is a separate 1800 sq. ft. residence with own private entrance. Two queen beds, plus two pull out full sized beds and single mattress for kids. Sunlit ensuite-bathroom with double sink, large soaker-tub and shower upstairs. Dwn-Strs bathroom has large shower. Huge walk-in closet upstairs. Loft area with cathedral ceilings creates open feel for entertaining or relaxing. Fully equipped kitchen with service for eight. 2 flat-screen T.V.’s with full list of Direc-TV channels and hi-speed internet access. Shopping, restaurants, grocery, Starbucks and Jamba Juice less than a mile. Getty Museum and Universal Studios are a short drive, and Disneyland is under 45 miles. Close access to westside of Los Angeles (Beverly Hills, Century City, Santa Monica, etc.), and less than one mile from some of the best hiking trails in the city. You'll have access to: Remote gated driveway entry Entire guest home Private Entry Entire Backyard & Pool Private Parking We are here for our guests anytime, and usually never more than a few minutes away. Located in an enclave of multi-million dollar residences, the Encino area is home to many celebrities, and is one of the most desirable neighborhoods in all of Los Angeles. Explore close by Ventura Boulevard, a 20-mile stretch of shopping, restaurants, eclectic shops and more. Centrally located to Beverly Hills, beaches, museums and downtown, this area truly has it all. Please note that we have 2 very friendly dogs that live in the main residence. They are NEVER allowed in the guest house, whether we have guests in residence or not. If you or your family has an allergy or is otherwise disinclined to be around dogs, it's quite easy for us to make sure that they are confined to areas where guests won't interact with them when they are coming, going or in the backyard. If not, and you'd like to meet our pooches, then "woof-woof," because they'd love to meet you!

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, 113 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 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, 741 reviews

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

Unwind in our studio guesthouse, tucked away in a peaceful backyard retreat with a large private pool, cabana, massage chair, and hot tub. Immerse yourself in paradise, surrounded by tropical fruit trees, an organic garden, and an aquaponics system. Outdoor bliss awaits for 420 enthusiasts (outdoors only). Mention '420 friendly' while booking to receive a gift of our homegrown, pesticide-free cannabis. Max 2 guests, no exceptions. Kindly review our description and house rules before booking.

Top guest favorite
Apartment in Downtown Los Angeles
4.97 out of 5 average rating, 176 reviews

Penthouse Suite LA 2BD/3BA [Hollywood Sign | Pool]

⭐️ PROPERTY IS LOCATED IN LOS ANGELES! ⭐️ PLEASE SEE PICTURES FOR ACCURATE LOCATION. THANK YOU! Breathtaking, sweeping panoramic penthouse views of Hollywood Hills from your corner suite. Luxuriously appointed Italian and Miami design. - Free parking for 1 vehicle - Dual-king master suites rivaling any 5-star hotel - Conveniently located in Koreatown, between Hollywood / Downtown LA Crypto Arena Perfect for vacation or business travel. Enjoy the beautiful sunset every day Travel in style

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 View Park-Windsor Hills
4.96 out of 5 average rating, 204 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 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 Los Angeles
4.88 out of 5 average rating, 104 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.

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 View Park-Windsor Hills
4.81 out of 5 average rating, 250 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
4.77 out of 5 average rating, 381 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
Home in Fullerton
4.95 out of 5 average rating, 143 reviews

Artistic Resort Pool Home with Private Oasis Yard

Art-filled retreat with unique artifacts, a lush garden with vibrant plants and vegetation, small pond, private pool & spa, firepit, and outdoor kitchen. Relax in a quiet cul-de-sac with two shaded patios, modern entertainment including streaming TVs, surround sound, a small pool table, and an Xbox. Ideal for families, friends, couples, or business travelers seeking comfort, privacy, and a memorable Southern California stay near Disneyland and major attractions.

Guest favorite
Home in Mid - Wilshire
4.91 out of 5 average rating, 337 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 illuminated saltwater pool reflects the surrounding greenery and soft outdoor lights. The enormous wood-framed glass window of the guest house is visible, providing a view of the inviting interior. The tranquil water creates a serene atmosphere in the evening light.
Guesthouse in Hollywood Hills
4.99 out of 5 average rating, 158 reviews

Hollywood Romantic Guest House & Pool

A beautifully designed, newly renovated Hollywood 1920’s guest house. An open concept space, and an enormous wood-framed glass window that looks onto a lagoon style salt-water pool. This unique guest house has the convenience of being walking distance from the Hollywood Walk of Fame, Grauman’s Chinese Theatre, Runyon Canyon, Sunset Blvd, restaurants, and many other Hollywood attractions.

Top guest favorite
A modern guesthouse is set within a spacious, landscaped area, featuring a smooth driveway and lush greenery. Sunshades are positioned over a patio area, while the entrance showcases welcoming accents and multiple windows, blending functionality with a calming outdoor environment.
Guesthouse in Tarzana
4.96 out of 5 average rating, 137 reviews

Luxurious Resort-Style Guesthouse

Relax in a luxurious 1400 sq ft. fully furnished and equipped guesthouse located on a lavish 1 acre property in "Melody Acres" Tarzana, CA. The grounds include a pool, a grassy area to relax, and private parking. Its a two bedroom two bath property with a chefs kitchen, washer and dryer, tvs in every room and a gorgeous large patio with a firepit and bbq to host an outdoor dinner.

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 G$10,460 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,450 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!