
Vacation 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.

The Paradise Hot-Tub Treehouse
Rejuvenate and play the piano in a secluded hot tub (& cold plunge!) under the stars, surrounded by tropical plants & fruit trees, with Big-Sur-style luxury hidden in the heart of Silverlake. On this quiet cul-de-sac, you may forget you're just a short walk to the best cafes & restaurants of Silverlake. The house boasts two private view decks, a desert & citrus garden, a pond, a fire pit, & a detached meditation/work room. Featured as one of 12 "dream homes" for rent in Los Angeles Magazine!

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.

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.

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.

The Lofts: Rooftop Pool & Spa, Free Parking, DTLA
Enjoy this music-themed DTLA Loft with free parking, a very rare find in an amazing location. Very family friendly, close to sites, quiet, and respectful neighbors. Very unique space! This unit has a living room, kitchen, bedroom and bath, Enjoy everything about Los Angeles from this amazing loft! PLEASE NOTE: The rooftop area, including the pool and hot tub, is currently CLOSED for construction and will remain UNAVAILABLE until September 29, 2025.

MULHOLLAND HILLS RETREAT W/BEST VIEWS IN LA
LOCATION, LOCATION, LOCATION. This iconic property is situated on a highly coveted street in the Mulholland Corridor near Beverly Hills, Sherman oaks, and Bel Air. The architecture, walls of glass, open floor plan & indoor/outdoor flow celebrate the California lifestyle. This Beverly Ridge residence has an emphasis on clean lines, open spaces and inspired architecture.

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!

J-Boho Chic Condo-Free Parking-Rooftop Pool & Spa
Beautiful 1 Bedroom condo on historical Broadway Blvd. Right next to Ace Hotel, this building used to be the largest costume shop in the world. Actor's like Charlie Chaplin used to come and pick up their attire here. 20ft+ceilings & views of the sunsets and city lights have you feeling the vibes during the evening hours. Includes TV and fast WIFI.

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.

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.

Pool House Oasis Close to Venice & Marina
This newer 3 bed/2bath duplex style home is centrally located between Venice & Marina Del Rey. Walking distance to local restaurants, markets, shops, and bars and about 1.5 miles to the beach, 5 miles to the airport and 8 miles to Sofi stadium. The backyard pool and spa is exclusively for your use!

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
Popular amenities for Westchester rentals with a pool
House rentals with a pool

3600 sq foot Luxury Spanish Pool Mansion

King Suite | HTD Pool | BBQ | Newly Renovated

Heated Pool & Spa, BBQ, Pool Table, Games, Private

Honeymoon House in Hollywood Hills

Mermaid Manor* Colorful Cozy Coastal Gem

THE ADALYN - Outdoor Living, Sparkling Pool+Spa

MermaidsCoveLA- A hidden oasis in Los Angeles

Sunny House minutes from the beach!
Condo rentals with a pool

Luxury 2 BR Glendale condo with pool

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Skyline view Condo, Free Parking, Jacuzzi

Stylish Modern industrial condo with Rooftop pool

Your Stylish Home Away From Home In Downtown LA!

Cozy 2 Bedroom/ 2 Bath Condo Minutes From DTLB

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

DTLA 2BR Condo w/ Pool & Free Parking
Home rentals with a private pool

2 BR Mediterranean Oasis Sleeps 6!

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

Mid-Century Hills Home • Pool, 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

Designer’s Dream Oasis with Lap Pool & Hot Tub
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ679 | ﺩ.ﺇ657 | ﺩ.ﺇ683 | ﺩ.ﺇ661 | ﺩ.ﺇ654 | ﺩ.ﺇ657 | ﺩ.ﺇ690 | ﺩ.ﺇ698 | ﺩ.ﺇ635 | ﺩ.ﺇ687 | ﺩ.ﺇ668 | ﺩ.ﺇ716 |
| 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 vacation rentals with a pool in Westchester

Total vacation rentals
Explore 250 vacation rentals in Westchester

Nightly prices starting at
Westchester vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 2,960 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
250 of Westchester vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
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- 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
- Los Angeles State Historic Park
- Knott’S Berry Farm
- Beverly Center
- Santa Monica Pier
- Anaheim Convention Center
- Long Beach Convention & Entertainment Center
- Disney California Adventure Park
- Beach House
- Silver Strand State Beach
- The Grove
- Mountain High




