
Holiday rentals with a pool in Westchester
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westchester
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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

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.

Private pool-side casita with stunning views!
This secluded, gated, lux retreat with stunning views sits on over 1 acre in a country-like setting with easy access to LA activities. Resort features include steam shower, filtered water, fire pit, pool, hammock, Alexa, 50” TV , hi-speed wi-fi, printer, desk, Nespresso coffee maker, BBQ w burner/pots/pans, remote controlled black out blinds, private patio, with luxury amenities and designer details. For reservations more than 3 months in advance, please inquire.

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.

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.

Ocean View From DTLA Skyscraper
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 views from the Griffith Observatory in the north, to Long Beach to the south, take in the vast expanse of Los Angeles with views to the Pacific Ocean.

Hasta La Vista w/ 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!

Venice Beach Guest Studio with Pool and Hot Tub
You have a charming Spanish 1926 architecture pool house. It’s located in the back of my house with all of the amenities necessary to enjoy your stay. ***MUST LOVE DOGS: I have 1 small friendly dog that lives with me in my house in front, I will keep him inside for the most part while you are here, but he will be around.

Urban Retreat
Detached guest house nestled on a hilltop within a completely private compound. Our home is our sanctuary, a place to escape the hustle and bustle of the city. Yet, we are right in the middle of the city! Home Sharing Registration Number: HSR19-000268

Sunny House minutes from the beach!
Relax at our sunny home. This home offers 3 bedroom, 2 baths, a fireplace, a custom gourmet kitchen, and salt water pool. This vacation paradise is centrally located: about 3 miles from the beach, 1 mile from Culver City, and only 3 miles from LAX.
Popular amenities for Westchester rentals with a pool
House rentals with a pool

New Toluca Lake Private Pool House

Midcentury Modern home with tons of Natural light!

Relaxing Spanish Stunner House near the Queen Mary

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

Honeymoon House in Hollywood Hills

Pool House Oasis Close to Venice & Marina

Resort style villa home/pool & jacuzzi, king bed

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

Stylish Modern industrial condo with Rooftop pool

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Skyline view Condo, Free Parking, Jacuzzi

Your Stylish Home Away From Home In Downtown LA!

Beautiful 2-BR Loft in DTLA w/ Rooftop Pool

Luxury Condo in the heart of DTLA

Luxury Top Floor DTLA Condo w/Pool *Free Parking*

DTLA Elegance & Style (1 bdrm, Free Parking, Pool)
Home rentals with a private pool

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

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

Designer’s Dream Oasis with Lap Pool & Hot Tub

Historical Swiss Chalet in Los Angeles (with pool)

Private Chic Guest Suite Beachwood Canyon Pool/Spa
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $276 AUD | $267 AUD | $278 AUD | $269 AUD | $266 AUD | $267 AUD | $281 AUD | $283 AUD | $258 AUD | $291 AUD | $275 AUD | $270 AUD |
| Avg. temp | 14°C | 14°C | 15°C | 16°C | 18°C | 19°C | 21°C | 22°C | 21°C | 20°C | 17°C | 14°C |
Quick stats about holiday rentals with a pool in Westchester

Total holiday rentals
Explore 230 holiday rentals in Westchester

Nightly prices starting at
Westchester holiday rentals start at $60 AUD per night before taxes and fees

Verified guest reviews
Over 2,640 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
230 of Westchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Westchester rentals

4.7 Average rating
Westchester stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Westchester's top spots, include Loyola Marymount University, Cinemark 18 and XD Los Angeles, and Aviation/LAX Station
Destinations to explore
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