Guest house holiday rentals in San Diego Bay

4.93 out of 5 average rating, 287 reviews

Enjoy North Park at Comfy & Chic Bungalow Retreat

This thoughtfully decorated bungalow boasts high ceilings, natural sunlight & a spacious, open-concept floor plan. Explore breweries, restaurants & boutique shopping nearby that are sure to give you a satisfying taste of the local San Diego scene! Please reach out if you need to access a car through one of my Turo vehicles during your stay. We built our back house from the ground up. All finishing touches are new and comfortable. The bungalow is a comfortable 680 sq ft 1 bedroom home. We live on site in the front house and are available if you need anything. With your own alley parking and coded gate entry, you will have privacy. Our backyard sits between both houses. We do have children that enjoy playing in the yard but we are mindful when we have guests to assure you are not disturbed. The lovely private outdoor space with the bungalow is fenced off from our yard and provides you a cozy outdoor area all to yourself. It has a bbq grill and seating. We are walking distance to two neighborhood markets, pizza, brewery, coffee shop, ice cream, and BBQ spot. The brewery has a different food truck every evening of the week. Lot's of options in just an 8 block walk thru a darling neighborhood. And just a little further off within 12 blocks are so many more options! We have a couple bikes we are happy to loan out. You park in the alley and access the bungalow from the alley side gate. This home is on the back end of our property which again is why it has alley access. There are many homes along the alley on both sides as it is very common for double lots in San Diego to have a “back house”. The alley is well lite at all times and we do have motion sensor lights around the property to light it well as you come and go when it is dark out. Many other cars also park in the alley as it is the main access to the homes on the other side of the alley...meaning this alley way is well kept and acts as the front entrance to the houses across the alley. Just to paint a picture that it isn’t a creepy alley haha The gate is coded for easy entry, as is the front door. No keys necessary! And to make it even easier...you get to choose the 4 digit code! We aim to make your visit a fun and memorable experience. It can be hard to arrive after a long day of travel to an unfamiliar place. We are happy to stock the kitchen with your grocery list of requests. In addition, if you are on a special trip and would like to add any surprises such as flowers or wine, we can also make that happen! Such additional services will be invoiced separately. From craft beers to coffee shops, North Park is sure to satisfy your taste buds! A variety of local shops + restaurants=your hardest vacay decision...choosing which ones to visit! North Park is ranked third-hottest hipster neighborhood in America. nearest bus stop is 12 blocks away. Bikes available upon request. We suggest Uber for the most popular and cost effective way if you are in need of transportation. This is not a party house. We are a young family and like to have fun and want you to enjoy your vacation, but no loud disturbances and large groups. No entertaining and late night shinanagins that will disturb our neighbors. Families are welcome but the home is not suited for those with small children under 3 as it is not a child proof environment.

5 out of 5 average rating, 202 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!

5 out of 5 average rating, 528 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, 494 reviews

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!

4.97 out of 5 average rating, 256 reviews

Beautiful Historic Home and Gardens Near Downtown!

Location, Location, Location...Welcome to Union Street Gardens. We are dedicated to providing a peaceful, serene atmosphere in which our guests can relax after a long day of exploring beautiful, sunny San Diego. This unique historic craftsman bungalow is just minutes from downtown, Balboa Park, the Zoo, beaches, and includes a Chef's kitchen, outdoor deck, gardens, fire pit and spa! Perfect for a family of 4 or two couples. Sorry no parties or large groups and no external guests please.

4.97 out of 5 average rating, 105 reviews

Breathtaking Ocean Views-Sunset Cliffs/Ocean Beach

Experience our stylish second story 1BR/1.5BA guesthouse with ocean, city, and mountain views in Point Loma. Perfect for couples, solo adventurers, and business travelers, this family-managed retreat offers a welcoming open-concept living space, equipped modern kitchen, and a tranquil bedroom with multiple balconies. 5 blocks from the ocean, it's the perfect coastal escape. Explore San Diego's attractions, including Old Town, Gaslamp, & Balboa Park. Book now for an unforgettable stay.

4.98 out of 5 average rating, 132 reviews

New (2022) North Park Abode w/ Roof Deck

Based in the heart of San Diego and one of the city's trendiest neighborhoods, our newly finished (in Summer 2022) ground level abode offers comfort, location, and style! We have a one bedroom/ one bathroom with separate living space. The beautiful La Cantina Doors open out to a freshly laid patio with comfortable Adirondack chairs and fire pit. Or, relax on the rooftop deck to enjoy those gorgeous San Diego sunsets! Our rental is also child friendly!

4.96 out of 5 average rating, 118 reviews

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

This is the perfect Guest House with a salted & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

4.99 out of 5 average rating, 407 reviews

*Private Canyon Retreat: Your Own Guesthouse*

An airy 1BD guest house at the end of a quiet dead-end street that overlooks a tranquil canyon....and an owner that works hard to create a fabulous experience for each guest; not just “another average rental”. With private entrance, full kitchen & bath, and double french doors opening onto a 400 sq ft deck with canyon views, it's the ideal retreat to come back to after exploring San Diego. Come fall in love with your next home away from home!

4.97 out of 5 average rating, 240 reviews

Fresh, hip and cozy private North Park guest house

Enjoy peaceful sunny San Diego days listening to the palm trees sway in this private backyard garden retreat set behind a 1925 California craftsman. The guest house is tucked away in a quiet quintessential Southern California neighborhood while only being a short and easy walk to amazing restaurants, world class breweries and cozy coffee shops. Balboa Park, the San Diego Zoo, beaches and downtown are all a few minutes drive away.

4.9 out of 5 average rating, 879 reviews

Casita–Hot Tub/Sauna/eBikes/Cold Plunge+Beach Gear

See more of our space and vibe by searching “The Birds & The Trees Vacations” online. California dreaming in our vintage citrus-themed casita! This sweet little guest suite has everything you need: full kitchen, cozy bed, and thoughtful extras. Relax in the outdoor wellness oasis (infrared sauna, jacuzzi, fire pit), and take advantage of access to electric scooters and our new fully stocked Ultimate Beach Kit for Summer 2025!