
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.

Designer’s Dream Oasis with Lap Pool & Hot Tub
Relax in the oasis of this wholly remodeled 1920s Craftsman-style guest house, dubbed the Boat House due to its proximity to the LA River. Impeccably designed brick industrial with intimate light-filled interiors, the Boat House has its own entrance and shares a large yard, fire pit, lap pool, and hot tub with the main house 50 feet away. NOTE: Euro-style kitchen includes refrigerator, toaster oven, portable electric cooktop (two burners), microwave, electric kettle for making coffee, teas, pots, pans, plates, etc. Street parking is usually never an issue. Please read the online manual. Modern, comfortable, loft-like space in hip East LA hood, Glassell Park! (FYI, it's not a real a boat house), but a unique 1920s brick building on a quiet residential street. We call it the "Boat House" because of close proximity to the LA River. The building has polished concrete floors, wood beams, mid-century design, custom copper faucets, custom OSB cabinetry & one-of-a-kind art & furnishings. There's a cozy fire-pit area right outside the door to enjoy as well as a pool, spa and fruit trees. NO FILM SHOOTS ALLOWED. PLEASE DON'T INQUIRE UNLESS PLANNING TO PAY 4X THE RATE. We lovingly designed, carefully curated and restored the guest house. We so appreciate you treading kindly with respect to the furnishings and items that share the space - (ie, please don't take the vintage pottery outdoors), typewriter (just for show), artwork, collection of books & furniture. PLEASE, NO WET TOWELS or bathing suits hung anywhere but on the hooks provided or in bathroom. There are blinds in the rooms for your privacy. The building is historic so thank you for being mindful and not putting anything other than Toilet paper in the toilet. Thank you!! The guest house shares a spacious back yard with the main house where we live. The backyard has fruit trees & a cozy fire pit. You have a private entry through a side gate. Ample street parking. We're an active family with two small kids. We live in the main house on site. We also have a chill labradoodle dog named Mel & two outdoor kitties. My hubby and I are both documentary filmmakers & have travelled extensively. We love hosting folks from all over so please say hello during your stay! We've provided blinds in the guest house and respect your privacy (we won't be too loud too early). We share our backyard with you and love to enjoy the outdoor space. We swim often, BBQ and use the firepit. Feel free to join us! (if the pool safety net is in place, please don't try and remove it yourself, thx). Please let us know if you'd like to use the pool and/or spa. The pool is heated by the sun but the spa can be quickly heated for your enjoyment. Just ask! Occasionally, we host friends, brunch & parties. Again, feel free to join in! We're easy going like that. Someone is usually on site to help with your needs or just a phone call or text away. Enjoy your stay! The guest house is located behind the main house on a quiet street, close to great coffee shops and restaurants. East LA is both hip and full of colorful diversity. The location is convenient to Silverlake, Los Feliz, Griffith Park, and Downtown. Ride sharing works great! We recommend it - Lyft or Uber. Also, various metro lines are located a couple miles away. And, Enterprise car rental has locations nearby. We're conveniently located near the 5 and 210 freeways. We live in a very ethnically diverse neighborhood. A few times a year some of our neighbors have parties: Quinceaneras, birthdays, Tomborazo bands, etc. We've never found them to be intrusive & rather enjoy the festive music!

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.

Adorable Back House w/Secluded Garden & Yard
Stylish private pool house available with queen bed, kitchen, bathroom, desk and working area, patio, heated pool*, and garden. The unit is self-contained and opens onto a private, secure, and fenced backyard shared with the main house. Lots of great details, pet friendly, kitchen and bath, vaulted ceilings, laundry, high-speed internet, and EV car charging, in a peaceful quiet area just at the edge of Pasadena. 20 minutes to downtown LA, 7 mins to downtown Pasadena. *extra fee to heat pool

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.

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! 🏡

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!

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.

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!

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.

King Suite | HTD Pool | BBQ | Newly Renovated
Enjoy a wonderful stay in this completely renovated home in Tarzana. This is a 4-bedroom, 2-bathroom home with 1 Cal king suite, 3 queen, and 1 full size beds, and a beautiful backyard with a large pool, BBQ set, and outdoor seating and dining. Conveniently located near the following tourist attractions: A 25-minute drive to Universal Studios, 25 minutes to Hollywood, 35 minutes to Downtown LA, 25 minutes to Malibu, and 1 hour to Disneyland.

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!

DTLA Skyscraper With City Views
Experience Downtown Los Angeles from the top of its skyline. Whether you're in town for a convention, show, sporting event or weekend away, you'll love the luxurious amenities and incredible view this listing has to offer. With absolutely stunning views of downtown, watch the organized chaos from high above in our tranquil condo.
Popular amenities for Windsor Hills rentals with a pool
House rentals with a pool

MULHOLLAND HILLS RETREAT W/BEST VIEWS IN LA

3600 sq foot Luxury Spanish Pool Mansion

Pool | King Bd | AC | LAX | SoFi | Beaches

Resort-style 3BD, heated spa, walk to shops/cafés

Pool House Oasis Close to Venice & Marina

Resort style villa home/pool & jacuzzi, king bed

Chic LA Studio • Pool • Patio • Free Parking • B.H

THE ADALYN - Outdoor Living, Sparkling Pool+Spa
Apartment rentals with a pool

⁎Art Deco Condo⁎ pool ⁎ Gym⁎ Free Parking ⁎Jacuzzi

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Stylish Modern industrial condo with Rooftop pool

Your Stylish Home Away From Home In Downtown LA!

DTLA 2BR Condo w/ Pool & Free Parking

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

Magnificent 2 BR apartment in Glendale, pool&gym

Luxury Condo in the heart of DTLA
Home rentals with a private pool

The Naples Island Pool House

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

Cozy Mid-Century Pad Fab Views & Fireplace

Contemporary Cottage - An Oasis with a Private Heated Pool.

Serene Cozy Guesthouse Garden Oasis

Keep Cool in the Poolside Shade at a Charming Encino House

Pool Oasis in Vintage Craftsman House

Historical Swiss Chalet in Los Angeles (with 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 £37 per night before taxes and fees

Verified guest reviews
Over 1,560 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Windsor Hills holiday rentals include wifi 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!
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- Rentals with pools View Park-Windsor Hills
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- Venice Beach
- Santa Catalina Island
- Los Angeles Convention Center
- Disneyland Park
- Santa Monica Beach
- Crypto.com Arena
- SoFi Stadium
- University of Southern California
- University of California - Los Angeles
- Santa Monica State Beach
- Universal Studios Hollywood
- Rose Bowl Stadium
- Six Flags Magic Mountain
- Beverly Center
- Knott’S Berry Farm
- Disney California Adventure Park
- Long Beach Convention & Entertainment Center
- Bolsa Chica State Beach
- Honda Center
- Hollywood Walk of Fame
- Topanga Beach
- Huntington Beach, California
- Angel Stadium of Anaheim
- California Institute of Technology




