
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.

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!

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

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!

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 short 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! 🏡

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.

Peaceful LA Studio Guesthouse. Garden, Pool & View
Relax in this serene Los Angeles quiet retreat on a peaceful private estate near Highland Park and adjacent to Pasadena, 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, set on a secure, gated property with dedicated off-street parking for guests. A curated original collection of art and photography books is available for guest use.

Deco Modern 1BR/1BA Loft in DTLA w 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 $15/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.

Hollywood Hills/Sunset Strip Marmont Retreat
Stylishly re-imagined mid-century modern with a pool and perfect location in the Hollywood Hills, just above Sunset Strip. The essence of SoCal chic, the artsy rock-and-roll vibe of this fully re-built and newly furnished three bedroom hideaway evokes the history of its Chateau Marmont neighbor, while delighting guests with the modern touches of a designer home. We welcome you to this architectural gem and endeavor to provide you with a unique and memorable stay.

Topanga Pool House
The Topanga Pool House is a resort like property located at the edge of the State Park, with canyon views & ocean breezes. The infrared sauna, cedar plunge pool, hot tub, outdoor bed and yoga deck provide an escape from the hustle of the city. Guests have said it's "as if you have a resort to yourselves" "spa like" "magical and healing" and that's the experience we strive to provide. We live in the upstairs unit but prioritize guest's privacy at all times.

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.

Studio Cottage
This is a small Studio cottage at the rear of my home. It's craftsmanesk in style with a partially open ceiling and a skylight. It's perfect for a couple or single person. There is a swimming pool but it's not heated, fine for swimming June to Oct depending on the weather, unless you are a polar bear. It's a 5 min walk to the MetroGold Line and a 10 min walk to new restaurants on Figueroa St. I have a fairly extensive cactus / succulent garden.

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.
Popular amenities for Windsor Hills rentals with a pool
House rentals with a pool

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Midcentury Modern home with tons of Natural light!

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

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Honeymoon House in Hollywood Hills

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Mermaid Manor* Colorful Cozy Coastal Gem
Condo rentals with a pool

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

Stylish Modern industrial condo with Rooftop pool

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Your Stylish Home Away From Home In Downtown LA!

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

Charming Loft-Rooftop Pool, Spa & FREE parking

Luxury Condo in the heart of DTLA

Luxury Top Floor DTLA Condo w/Pool *Free Parking*
Home rentals with a private pool

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

Cozy Mid-Century Pad Fab Views & Fireplace

Contemporary Cottage - An Oasis with a Private Heated Pool.

Keep Cool in the Poolside Shade at a Charming Encino House

Serene Cozy Guesthouse Garden Oasis

Pool Oasis in Vintage Craftsman House

Historical Swiss Chalet in Los Angeles (with pool)

Private Chic Guest Suite Beachwood Canyon Pool/Spa
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 € 42 per night before taxes and fees

Verified guest reviews
Over 1,560 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!
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