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Vacation rentals with a pool in Highland Park

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Highland Park

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern guesthouse with white stucco walls and arched windows is seen beside a sparkling pool. Colorful landscaping provides a cheerful backdrop, while a shaded area with a white umbrella offers a spot for relaxation. Steps lead from the pool area to the entrance of the guesthouse.
Guesthouse in Eagle Rock
4.99 out of 5 average rating, 156 reviews

Private Spanish Guesthouse w/ Pool & Views

Welcome to Casita Bonita-a newly constructed guesthouse nestled in the hills of beautiful Eagle Rock, Los Angeles. Whether you're seeking a quiet weekend getaway, or simply looking to unwind in a peaceful and relaxing environment, our private guesthouse is perfect for you! This secluded 1 bedroom guesthouse with kitchenette and full bathroom has all the amenities you need for your stay. Take in the gorgeous views as you sip your morning coffee on a spacious deck overlooking the sparkling pool.

Guest favorite
A spacious living area is illuminated by natural light through large windows. The wooden vaulted ceiling adds warmth, while a comfortable sectional sofa with decorative pillows faces a wooden coffee table. A dining area and modern kitchen are visible in the background, enhancing the homey ambiance.
Home in Silver Lake
4.97 out of 5 average rating, 370 reviews

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!

Superhost
Home in Highland Park
4.83 out of 5 average rating, 115 reviews

Designer home in hip Highland Park w/ pool & hotub

Our Highland Park home is bursting with color and beautiful design details. The owner is a well-known interior designer. Gorgeous front and back yard with a cowboy pool, hot tub, and gas fire-pit. Located in one of LA's hippest and most sought after neighborhoods Highland Park. We are walking distance to the two main streets York and Figueroa. Walking distance to the subway and 10 Minuets to Downtown LA. The perfect stay in every way! Los Angeles Home-Sharing Registration Number: HSR23-003040

Guest favorite
An outdoor seating area features a round stone table surrounded by iron chairs beneath a large umbrella. Lush greenery and small shrubs frame the space, adding to the serene environment, while a brick pathway leads towards the garden area.
Bungalow in Pasadena
4.89 out of 5 average rating, 208 reviews

Cottage@5 star Resort 2R 2B Kitchen 1 free parking

Selected The Best Top 50 Resort in the world. Cottage was part of Ritz Carlton until was sold to the current management. Now is private own. No relationships with current Langham hotel Excellent for those who appreciate style, refinement, trees, quiet,privacy & location. Within 2 min walk to 110 years historical resort's Poolside cafe, Jazz Bar, Grill house AfternoonTea houseYou will enjoy the beautiful garden & old trees surrounding. Surround by Historical stylish mansions neighborhood

Top guest favorite
The exterior of the villa is showcased at twilight, highlighting the swimming pool reflecting soft light. A spacious deck with lounge chairs is visible, along with a serene yard and bamboo greenery that provides privacy. Warm interior lights are seen through the glass sliding doors.
Home in Silver Lake
4.94 out of 5 average rating, 128 reviews

Silverlake Midcentury Modern with Pool and Views

Your villa for your visit to LA, tucked in the peaceful Silverlake hills between Hollywood and downtown. Visit all the famous restaurants, shops, and culture of this hip upscale neighborhood, or stay home and renew your creative spirit, with artwork, piano, stylish modern blue swimming pool, spa, and sparking views in multiple directions of the downtown skyline, Silver Lake, the mountains. Beautiful sunsets daily. A quiet place for artists, writers, families, romance, and your rejuvenation.

Superhost
An inviting pool area is surrounded by a beautifully landscaped yard, featuring lounge chairs and a shaded outdoor seating arrangement. String lights illuminate the scene, creating a relaxing ambiance under the evening sky.
Home in Pasadena
4.89 out of 5 average rating, 257 reviews

Your Private Resort Near the Rose Bowl Awaits

My 3 bedroom two bath home sleeps 8 comfortably, and with a formal dining room and FULLY equipped kitchen, making memories with your family and friends is effortless. Take advantage of the beautiful California sunshine and enjoy the fully enclosed backyard and completely fenced front yard with SWIMMING POOL (the pool can be heated for an extra $75.00 charge per day) outdoor dining, and string lights for the perfect ambiance. Have a glass of wine or cold beer in my eclectic living room.

Guest favorite
Home in South Pasadena
4.89 out of 5 average rating, 122 reviews

New state of the art home on Historic Property

This new house is on the Historic Green and Green track, hidden down a long driveway. Designed for the owners to live in, expenses were not spared in construction or interior design. With a built in sound system and cinema style tv, you can float in the pool and enjoy both. The interior bath tub has heated walls. The kitchen is a chef’s dream. It has a walk in closet. You can charge your electric car in the gated driveway where your animals can run free. Barbecue area is included.

Top guest favorite
A spacious studio features a cozy queen-sized bed positioned near a light-filled window. A comfortable sofa and armchairs surround a modern coffee table, providing seating options. Wood flooring complements the contemporary furnishings, while shelves display a collection of books and art pieces.
Guesthouse in Highland Park
4.97 out of 5 average rating, 622 reviews

Modern Guesthouse in Highland Park: Pool & Parking

Relax in this serene, private Los Angeles retreat in Highland Park, set on a gated property near Pasadena and surrounded by a Mediterranean garden under the California sun. Ideal for guests seeking a quiet stay in a residential setting. This beautifully designed modern guest studio is a separate, stand-alone structure on an owner-occupied property, with access to a shared swimming pool and dedicated off-street parking. A curated art and photography book collection is available.

Top guest favorite
A spacious living area features a large gray sectional sofa adorned with yellow cushions. A wooden coffee table sits in front of it, and a television is placed on a matching low wood cabinet. Natural light streams in through a large window, illuminating the room.
Guest suite in Glendale
4.97 out of 5 average rating, 149 reviews

Spacious, private guest suite in great area

Well appointed, spacious, newly remodeled and furnished downstairs private guest suite in an exceptional area. Easy, unrestricted, nearby, safe parking on street. Private entrance. New king bed. Cedar wood hot rock sauna, large television, kitchen, and its own washer/dryer. Access to a shared private pool and jacuzzi. Private patio with chairs and table. Barbecue outside. No children or pets please. No smoking at any time inside. All basic amenities provided.

Top guest favorite
An outdoor deck features two lounge chairs and two playful, bright green floaties beside a sparkling pool. Umbrellas provide shade, while a glass wall offers views of lush greenery and natural surroundings, creating an inviting and serene environment.
Guesthouse in Los Angeles
4.98 out of 5 average rating, 171 reviews

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.

Top guest favorite
The exterior view of the studio cottage showcases a welcoming entrance surrounded by greenery. Two blue chairs and a small table are positioned in a sandy area, with garden features including foliage and decorative plants. Natural light filters through trees, creating a serene setting.
Cottage in Highland Park
4.93 out of 5 average rating, 456 reviews

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.

Guest favorite
A serene outdoor space features a beautifully designed lap pool adjacent to a spa, set against a backdrop of a brick guest house. Lush green grass surrounds the area, creating a peaceful environment. French doors provide access to the interior, enhancing the inviting atmosphere.
Guesthouse in Glassell Park
4.93 out of 5 average rating, 567 reviews

Designer’s Dream Oasis with Lap Pool & Hot Tub

Relax in this 1920s brick home with light-filled interiors, concrete floors, wood beams, copper faucets. Enjoy large yard, fire pit, lap pool, and spa. Euro kitchen-refrigerator, toaster oven, cooktop, microwave. Active family with pets (Murphy, large friendly dog + 2 small rescues - please watch for signs). Always on-site or a text away. Close to Eagle Rock, Highland Park, Silverlake, Los Feliz, downtown. Street parking usually always available.

Popular amenities for Highland Park rentals with a pool

When is the best time to visit Highland Park?

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Quick stats about vacation rentals with a pool in Highland Park

  • Total vacation rentals

    Explore 20 vacation rentals in Highland Park

  • Nightly prices starting at

    Highland Park vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,550 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 Highland Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Highland Park rentals

  • 4.8 Average rating

    Highland Park stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Highland Park's top spots, include Highland Theatre, Occidental College, and Highland Park Station