Guesthouse holiday rentals in Hillcrest

Guesthouse in Mission Hills

A curving staircase is visible, flanked by white walls and adorned with vibrant blue tiles. Handrails provide support along the ascent, leading to a bright upper space. A potted plant enhances the serene ambiance at the top of the stairs.

5 out of 5 average rating, 216 reviews

Santorini-Inspired Cottage w/ Hot Tub + Views

*CHECK OUT OUR OTHER AIRBNB* Travel 16 steps up a Greek-inspired curving stairway with 2-story high walls to your tucked-away cottage built into the hillside villa of Alta Colina. With spectacular views, step onto the balcony to watch planes take off & boats sail around the harbor. End the night in front of your secluded back patio fireplace or climb the steps of your spiral staircase to the rooftop Jacuzzi. European-inspired design & details, it'll be hard to believe you’re still in San Diego!

4.97 out of 5 average rating, 601 reviews

A private garden area features two large orange umbrellas shading wicker seating arrangements. Lush greenery and colorful potted plants surround the space, with a stone patio leading to a warm-toned guesthouse wall. A window on the guesthouse reflects natural light, enhancing the serene atmosphere.

Guesthouse in Kensington

Central & Serene Secret Garden Guesthouse

My cozy & stylish Garden Guesthouse features colorful decor that gives a fun, relaxed vibe. Relax in style inside or outside in my peaceful garden w a cup of coffee, or glass of wine. I love to say a hi to my guests yet your privacy is #1. Reach me via Airbnb app if I can help! Kensington is a central, 1920’s historic neighborhood w shops & great local eateries. Close to downtown, Gaslamp, Zoo, airport, beaches, Balboa Park. Bus stop, & trolley nearby. Reserved off street parking space too!

Guesthouse in Greater North Park

A kitchen area features modern cabinetry and a full-size refrigerator. A dining table is set for two, with glassware and dishware arranged neatly. Light streams through an open door, highlighting greenery just outside.

4.97 out of 5 average rating, 258 reviews

North Park, San Diego's Best At Your Doorstep

Incomparable location, privacy, quality and unique experiences await the discerning traveler. Walk to dozens of renown restaurants, coffee shops, micro-breweries, bars, art galleries, unique shops, stores and world famous attractions from your exceptional detached studio suite. Come see why Forbes Magazine, Time Magazine, The New York Times, The LA Times and The San Diego Union Tribune recently acclaimed North Park as San Diego's Favorite Neighborhood, The Hippest In The Nation and Smokin' Hot!

A serene garden area is showcased, featuring a variety of plants including flowering species with orange-tipped blossoms. A slate stone with the word 'WELCOME' is prominently displayed among smooth rocks, enhancing the inviting atmosphere of the space.

4.91 out of 5 average rating, 376 reviews

Private Hillcrest Retreat w/ Parking and AC

Good communication is of great value for this comfy, artsy studio and garden. Everyone is personally welcomed by your onsite Host. Walk to an international array of restaurants and clubs. About 2 mi to San Diego Zoo, SeaWorld, Balboa Park museums, Convention Center, Maritime Museum/USS Midway, Gaslamp Qtr, Little Italy, Old Town, Scripps Mercy & UCSD Med Center, shopping; about 10 mi to beaches. NO FULL KITCHEN. NO PARTIES OR UNREGISTERED GUESTS. Microwave, Keurig and mini-fridge are provided.

A tranquil koi pond is nestled within a landscaped garden, featuring several colorful koi fish swimming gracefully near the surface. Rocks and plants frame the pond, while a small waterfall cascades gently into the water, creating a soothing ambiance.

5 out of 5 average rating, 540 reviews

Waterhaven - A Pondside Oasis

Please read house rules before booking. Located in the Hillcrest area of San Diego just blocks to Balboa Park is Waterhaven, a non smoking, adults only retreat and the perfect place to enjoy your San Diego stay. 325 square feet, a fully private retreat that includes your own living space, bathroom, and kitchen. The guesthouse has dual paned windows, no shared walls, and the yard is fully protected with a stone wall for privacy and security. Waterhaven is a quiet, peaceful, relaxing experience.

4.95 out of 5 average rating, 505 reviews

A welcoming entrance features red brick steps leading up to a solid wooden door, framed by dark wooden beams. Lush greenery and potted plants accentuate the pathway, while large windows on either side provide natural light to the area.

Guesthouse in San Diego

Modern Sweet Home Stay, Hillcrest, A/C Parking W/D

This quaint bungalow sits in a prime location of Hillcrest, a highly desirable area in San Diego. It is very quiet and private and sits directly behind our house(pictured) with a beautifully landscaped brick courtyard. You are within walking distance to "The Heart of Hillcrest" where you will discover many fabulous restaurants, coffee and boutique shops, and so much more. We are a short Uber drive to downtown and everywhere else San Diego has to offer. We hope you stay with us soon!

Guesthouse in Greater North Park

The exterior of a renovated guesthouse is presented, featuring a white stucco facade with decorative tiles along the steps. A green door, large windows, and a charming walkway leading to the stairs enhance the inviting appearance of the property.

4.99 out of 5 average rating, 175 reviews

Carrie’s North Park Casita, in Heart of San Diego

Fully renovated stand-alone guesthouse in North Park, consistently voted one of the coolest neighborhoods in the US. Just a few blocks from all the action at 30th and University, but tucked away in a quiet, historically designated residential neighborhood. Walk to Balboa Park or The World Famous San Diego Zoo. Get to Downtown San Diego, San Diego International Airport, Old Town, Little Italy, Coronado, La Jolla, Sea World, multiple beaches & so much more in under 15 minutes.

A private outdoor seating area is showcased on a rooftop terrace, featuring two armchairs and a spacious couch, all adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by lush greenery and palm trees. The sunset casts a warm glow over the scene.

5 out of 5 average rating, 118 reviews

Rooftop views 10min walk to Balboa Park/Zoo/Bars

Enjoy this peaceful second-story new guesthouse overlooking the treetops! A perfect day might be a morning stroll through Balboa Park, the cultural center of San Diego, surrounded by 58 miles of walking and running trails, followed by a short walk to the super fun bars and restaurants of Hillcrest, North Park, and University Heights. We LOVE this neighborhood and we are so excited to share the beauty, culture, and welcoming vibe of it with our guests!

An outdoor patio is surrounded by lush greenery, featuring vibrant flowers and ferns. A rustic wooden feature stands to one side, complementing the warm-toned brick flooring. A large glass door provides access to the interior, inviting natural light into the space.

4.89 out of 5 average rating, 222 reviews

Relaxing Oasis - short walk to shops & recreation

The Zen Den- This small oasis boasts a location that offers the best of both worlds: a quiet sanctuary for some tranquil R&R, and close proximity to San Diego’s best nightlife, sightseeing, and recreation. The studio opens up to an outdoor patio perfect for San Diego’s sunny and 70 weather. Your blissful retreat is located one block from the bustling metro district of Hillcrest with coffee shops, restaurants, parks, walking/running trails, and more.

Guesthouse in Greater North Park

A modern living space features a gray sectional sofa and a flat-screen television on a light entertainment unit. Natural light streams in through a sliding door, which opens to a balcony showcasing palm trees and clear blue skies. Minimalist shelving holds potted plants enhancing the decor.

4.96 out of 5 average rating, 171 reviews

Brand New Modern North Park View Apartment

This brand new North Park apartment is the perfect place to enjoy San Diego. The home is located on a quiet street in close proximity to Balboa Park, the San Diego Zoo, Downtown, Sea World, Old Town, Coronado Island, Seaport Village, and the airport. It is in walking distance to a number of renown restaurants, coffee shops, and breweries. Beautiful sunset views allow you to relax after a long day of taking in the city.

Guesthouse in Normal Heights

A spacious bedroom features a large king size bed with a textured blanket, complemented by a nightstand and a decorative lamp. Sliding glass doors open to a deck, allowing natural light to fill the room. A flat-screen TV and a desk are visible in the background.

4.98 out of 5 average rating, 444 reviews

Mountain View Retreat in Gated Estate (Hot Tub)

Perched above a canyon with spectacular panoramic mountain views, this private guest house is a secluded retreat in one of San Diego’s most eclectic and desirable neighborhoods less than 6 miles from the Downtown San Diego airport. Enjoy a fully equipped kitchen, luxe king size bed and dual sliding glass doors that open to an expansive deck with patio seating, private hot tub and BBQ area.

A well-appointed sitting area features patterned seating and decorative tables set on a vibrant area rug. A door opens to an outdoor patio with a small dining table and chairs, allowing for seamless indoor-outdoor access. Walls are adorned with various framed artwork.