Vacation rentals with a pool in Highland Park

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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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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, 547 reviews

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!

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, 142 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.

Top 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, 359 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!

Guest favorite
The spacious sleeping area features vaulted exposed beam ceilings and a queen bed with neutral bedding. A wooden desk is positioned nearby, complemented by a rolling chair, while a cozy seating area includes a soft armchair. Natural light enters through glass doors leading to the patio.
Guesthouse in Altadena
4.92 out of 5 average rating, 210 reviews

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

Guest favorite
Home in Highland Park
4.88 out of 5 average rating, 106 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

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, 609 reviews

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.

Top guest favorite
Guesthouse in Alhambra
4.98 out of 5 average rating, 197 reviews

BeautifulApt! NearLA Attractions Hospitals&College

Our place is nearby many LA attractions! like, Downtown LA, Hollywood, Universal Studios, Griffith Park, The LA Zoo, LA Science Center, Staples Center, Convention Center, Dodgers Stadium, The Rose Bowl, Movie Theater, Comedy Club And more! There are Restaurants and Stores nearby. The bus top is walking distance. Freeways are nearby, like the 710,60,101,5, and 10 Freeways. Convenient for Students and traveling nurses since we have hospitals and College's nearby. Perfect for Any Stay!

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
4.96 out of 5 average rating, 137 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
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, 443 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.

Top guest favorite
A cozy room features a compact dresser with colorful drawers and a small television. A wooden shelf holds hangers above a sink area visible in the background. Natural light filters in through a nearby window, illuminating the warm-toned flooring.
Guesthouse in Los Angeles
4.94 out of 5 average rating, 185 reviews

Adorable Hillside Cabin

Charming detached, private, Guest Cabin available in Boyle Heights/City Terrace/near freeways. It's 7 minutes to the Arts District in DTLA, and adjacent to USC Medical Ctr and Cal State LA. This is an autonomous space on a large hillside property. Wifi and cable! The cabin is already sparkling clean, but in addition I will adhere strictly to the sanitizing and safety guidelines provided by Airbnb and the CDC.

Guest favorite
Apartment in Los Angeles
4.95 out of 5 average rating, 187 reviews

Luxury 5 Star DTLA Studio/FreeParking/KingBed/420

Apartment is in DOWNTOWN LOS ANGELES, on 8th and Spring St. **It is not located in Ramona Gardens!** you will get address after booking! • Any Unauthorized Parties/Group Gatherings Will Be Charged $500.00 • We are PET friendly and 420 friendly and offer free parking! Please do not book if that’s not suitable. Thank you • Luxury resort style complex including spectacular gym, pool, hot tub and rooftop.

Top guest favorite
The room includes a queen-size bed adorned with a floral coverlet, accompanied by a large mirror and nautical accents. A comfortable sofa and a desk with a chair provide additional seating. Soft lighting enhances the welcoming atmosphere, and a television is positioned for easy viewing.
Place to stay in Pasadena
4.95 out of 5 average rating, 418 reviews

Charming Guest Cottage

This 400 sq ft one room cottage sits in a beautiful very quite neighborhood. Guest will enjoy taking long walks in the near perfect year round weather. Super safe with lots of charming homes on tree lines streets. A five minute walk to the Mission Village where you can enjoy yummy foods from two different local restaurant's or shop at fabulous shops.

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 1,910 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