
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.

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!

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.

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.

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.

Penthouse LA 1bed/1bath [VIEWS | SKY SUITE | POOL]
⭐️ PROPERTY IS LOCATED IN KOREATOWN LOS ANGELES ⭐️ SEE PICTURES FOR ACCURATE LOCATION THANK YOU! [ Penthouse Suite ] * Downtown Skyline View * Free Parking for 1 vehicle * Private en-suite bathroom * Brand new 14” memory foam King bed * Perfect location between Hollywood and Downtown LA (Crypto Arena) * Close to all major attractions Ideal for vacation or business travel. Enjoy the beautiful LA sunsets every day =) Travel in style!

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!

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

New Toluca Lake Private Pool House

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Honeymoon House in Hollywood Hills

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Mermaid Manor* Colorful Cozy Coastal Gem

THE ADALYN - Outdoor Living, Sparkling Pool+Spa

MermaidsCoveLA- A hidden oasis in Los Angeles
Condo rentals with a pool

Art Deco Condo pool Gym Free Parking Jacuzzi

Skyline view Condo, Free Parking, Jacuzzi

Modern, Spacious 1 Bd Loft in DTLA - FREE Parking

Stylish Modern industrial condo with Rooftop pool

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

DTLA 2BR Condo w/ Pool & Free Parking

Beautiful 2-BR Loft in DTLA w/ Rooftop Pool

Magnificent 2 BR apartment in Glendale, pool&gym
Home rentals with a private pool

2 BR Mediterranean Oasis Sleeps 6!

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

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 | G$38,676 GYD | G$37,422 GYD | G$38,885 GYD | G$37,631 GYD | G$37,212 GYD | G$37,422 GYD | G$39,303 GYD | G$39,721 GYD | G$36,167 GYD | G$39,094 GYD | G$38,049 GYD | G$40,766 GYD |
| 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 G$8,362 GYD 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
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