Guest house holiday rentals in San Diego

Anna's Historic Stone Cottage w/panoramic View!

Welcome to Anna's Historic Stone Cottage! The 110 year old cottage has been transformed into the perfect combination of romantic and rustic for a dream-worthy getaway. The 280sq ft cottage features stunning, panoramic views of the San Diego skyline while offering rooftop seating for sunrise and sunset viewing. The Cottage is conveniently located 20 minutes from the world famous San Diego zoo and most other must-see, tourist spots. Amenities for special occasions offered too. Check out our menu!

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.

Loft Cabin•SoakTub•FirePit• Cinema•View+Zoo add-on

Tucked into a quiet hillside canyon above the city, this very private, nature-immersed retreat is just a short drive outside of downtown San Diego. Features include: ✦Private Hot Soaking Tub under the stars ✦Panoramic City views ✦Custom outdoor theatre ✦Queen bed - always white sheets ✦Fast Wi-Fi ✦New quiet AC/Heat ✦Gated, off street prkg Relax on your private patio, unwind in the outdoor hot soaking tub or rain shower and end the night with a movie at your very own "Cinema Under the Stars"!

Sparkling Clean & Plush Studio in PB w /AC

Thank you for checking out our awesome studio in the heart of Pacific Beach. This bright & open space is just 7 blocks from the beach and walking distance to restaurants, bars, shops, and nightlife. The studio has an open layout with high ceilings and a fresh coastal design. Guests also have access to a large shared patio with seating and a BBQ, perfect for relaxing outdoors. Enjoy air conditioning, 650 thread count luxury cotton linens, and a plush feather duvet for a cozy, restful stay!

The Golden Hill mosaic "casita"

This is a boutique guesthouse that is part of a 1913 duplex which has been extensively remodeled, and yet maintains its essence in historic Golden Hill. It is a solar-powered 1-bedroom 1-bathroom featuring custom Mexican furniture, french doors, a view of the San Diego Skyline, and a private patio area. Feel the cool breeze on top of Golden hill, a centrally located up and coming neighborhood with lots of walkable destinations. The home is exquisitely decorated with custom Chilean mosaics.

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

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Betty- Guesthouse near CBX & San Ysidro border

This comfy studio located in San Diego is the perfect spot for a quiet & cozy weekend retreat. Inside is bright & inviting with stylish spacious studio, private entrance from side gate, private patio with bbq & hanging hammocks; driveway parking spot & plenty of street parking! The view from the patio is very relaxing, making it the perfect weekend get away. Centrally located in a quiet & peaceful area within 5 minutes away from Plaza Las Americas & 10 minutes away from the CBX.

La Casita - Fully Updated Casita in Mission Hills

This well designed, fully updated detached studio casita is located in one of the most sought after neighborhoods in San Diego - Mission Hills. Surrounded by a serene garden courtyard with private entry and quiet patio. Close to great dining, grocery stores and shopping, and a mere 10 minutes or less to most of San Diego’s main attractions. If you are coming by car, there is plenty of free street parking - otherwise Ubers are plentiful and reasonably priced.

*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!

Casita in the Vineyard. Privacy & Beauty combine.

Enjoy our newly updated resort-style Casita with hot tub, propane fire pit, and shaded pagoda. This tranquil and private getaway has a full kitchen, bath and laundry facilities and is only 7 minutes from the San Diego Safari Park. Numerous vineyards in the popular “Highland Valley Wine Country”, some with live music and food, are within a 2 mile radius. Only 4 miles from Highway 15. See the stars, hear nature and relax.

OB Casita

Stay in a sweet Casita surrounded by a private garden. This in-law unit features a cozy kitchenette, a private bathroom, a BBQ, and a large fenced outdoor area perfect for pups! Sit under the avocado tree on the back deck and watch for the OB parrots. Or, take a short walk in this lively neighborhood to, beaches, dog beach, tennis courts, restaurants, bars, shopping, a playground, or a dog park.

Beach views for 2! Jacuzzi, fire pit

This mid-century modern jewel offers one of the best views in San Diego while still being walking distance (9 blocks) to the beach. You'll get a 1 bedroom with queen bed, full kitchen, living room with a convertible couch. I live upstairs and have a deck so you get your own private deck below me with a firepit and jacuzzi. Perfect place for a couple (or possibly a family with 2 small children).