
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.

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!

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.

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.

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

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!

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.

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.

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!

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.

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.

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.

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
House rentals with a pool

Stunning View Hollywood Hills Guest House

Lake Balboa Ranch Home with Pool & indoor Jacuzzi

Charming Spanish House w Pool in Historical Bixby

New Toluca Lake Private Pool House

Midcentury Modern home with tons of Natural light!

SoFi USC 10 mins ~ Pool ~ HotTub ~ Gym ~ West LA Retreat

Mediterranean Resort Style Living in Long Beach

Chic LA Studio • Pool • Patio • Free Parking • B.H
Condo rentals with a pool

⁎ArtDeco ⁎ Condo⁎ pool⁎ Gym⁎Free Parking⁎Jacuzzi

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Skyline view Condo, Free Parking, Jacuzzi

Fantastic Santa Monica Beach

DTLA 2BR Condo w/ Pool & Free Parking

Live Like a Legend In DTLA + 360° Pool + Parking

Charming Loft-Rooftop Pool, Spa & FREE parking

Beautiful 2-BR Loft in DTLA w/ Rooftop Pool
Home rentals with a private pool

2 BR Mediterranean Oasis Sleeps 6!

The Naples Island Pool House

Contemporary Cottage - An Oasis with a Private Heated Pool.

Serene Cozy Guesthouse Garden Oasis
101 Luxurious Home near Universal Studios Pool/Spa

Designer’s Dream Oasis with Lap Pool & Hot Tub

Historical Swiss Chalet in Los Angeles (with pool)

Your Private Resort in Southern California
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!
Destinations to explore
- Rentals with a fire pit Windsor Hills
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- Rentals with pools View Park-Windsor Hills
- Rentals with pools Los Angeles County
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- Rentals with pools United States
- Venice Beach
- Disneyland Park
- Santa Catalina Island
- Los Angeles Convention Center
- Santa Monica Beach
- Crypto.com Arena
- SoFi Stadium
- University of California - Los Angeles
- University of Southern California
- Universal Studios Hollywood
- Rose Bowl Stadium
- Santa Monica State Beach
- Six Flags Magic Mountain
- Knott’S Berry Farm
- Santa Monica Pier
- Anaheim Convention Center
- Long Beach Convention & Entertainment Center
- Disney California Adventure Park
- Beach House
- The Grove
- Mountain High
- Hollywood Walk of Fame
- Bolsa Chica State Beach
- Honda Center




