Holiday rentals with a pool in Highland Park

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.

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!

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

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

California Modern Guesthouse in LA, 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. Ideal for guests seeking a quiet stay in a residential setting. This 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. Thoughtfully furnished with art, photography books and modern interiors, it offers a comfortable base for exploring LA.

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.

Your Private Resort in Southern California

This private pool retreat boasts a yard begging you to enjoy the California sunshine! Pasadena’s quiet charm and excellent restaurant scene put you just outside bustling Downtown LA and some of California’s main sites, including Santa Monica Beach & Pier, Hollywood, Disneyland and an extensive coastline of beaches to explore. 13 mi to Downtown Los Angeles 16 mi to Universal Studios 17 mi to Hollywood 27 mi to Santa Monica 33 mi to Knots Berry Farm 40 mi to Disneyland STR # SRU2020-00091

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.

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.

Stylish LA Escape: Pool & BBQ

🚗WELCOME to the BEST of Los Angeles & Pasadena! ⛳️ This cozy, NEWLY REMODELED 2-bedroom, 2-bathroom house features a modern pool and is perfect for your California adventures! Located in Northeast LA, it offers easy access to downtown, Hollywood, Pasadena, and more attractions. Comfortably accommodates up to 5 guests. BOOK now and create lasting memories in this charming retreat! Please save our home by clicking the ❤️ so you can easily find it later and share with others!

Pool and Historical Swiss Chalet in Los Angeles

The Swiss Chalet is a historic home featuring original architecture and design. The Chalet also features lush gardens, a pool, and a hot tub on the private upper terrace. Enjoy the view of the mountains, bask in the sun by the pool, take in the sunset over a glass of wine from the veranda, and stargaze from the hot tub nestled between majestic pines and picturesque Californian oaks. Please note: no kitchen, and no parties. Glendale Home-Sharing License: HS-003915-2025

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.