Guesthouse vacation rentals in Rancho San Diego

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Rancho San Diego

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Spring Valley

4.99 out of 5 average rating, 327 reviews

Hot Soaking Tub+Night Cinema+Mtn & City Views!

Spectacular panoramic city lights and sunset views from this private cottage located just 20 minutes from Downtown, San Diego Zoo & the airport. Your retreat includes an outdoor hot soaking tub and "Cinema under the stars" - an outdoor movie experience like no other. Perfect for a special getaway on a unique, private gated property overlooking the city, the cottage features a cozy Queen bed, a 50” TV, fast wifi, a full kitchen and a/c & heat unit. Special discounts for stays of 4 nights or more!

Guest favorite

Guesthouse in La Mesa

4.98 out of 5 average rating, 172 reviews

Da Hui Hut - La Mesa’s best view and spa

Da Hui Hut is a very private oasis uniquely situated at the top of San Diego county's magnificent Mt. Helix. At roughly 1,300 feet above sea level, Mt. Helix is the crown jewel of natural landmarks in the area. The landscape provides bountiful views, and the large deck is positioned perfectly to see it all. It feels like you're on top of the city! Inside, guests will encounter Californian and Hawaiian inspired decor as they collide with wooden walls to compose a symphony of color and good vibes.

Guest favorite

Guesthouse in El Cajon

4.99 out of 5 average rating, 171 reviews

Modern mountain guest house. Incredible views

Neighboring San Diego, quaint country living with incredible views minutes from everything, breathtaking sunsets, 20 mins to beach, close by hiking trails, and only 3 minutes hop on the freeway. Full Kitchen, Laundry, and Living area and with beautiful furnishings, a perfect home away from home. Whether traveling for work or play we have had guests stay for a conference in San Diego or just to visit friends and hit the beach a few days, we look forward to you loving our home as much as we do.

Guest favorite

Guesthouse in El Cajon

4.97 out of 5 average rating, 146 reviews

Mt Helix Studio Loft with Mountain Views

Mountain Views: Freshly renovated, quiet and spacious studio loft in private neighborhood. Close to coffee shops, grocery stores, and quick access to major highways. 500 sqft open concept. Laundry, Fast Internet, Cable TV and streaming services. Additionally, if you like oranges and avocados we grow them on the property (Seasonal of course). We also have a chicken coop and fresh eggs on request. Security Deposit Hold and Signed Short-term Rental Agreement Required as we live on the property.

Guest favorite

Guesthouse in La Mesa

4.99 out of 5 average rating, 161 reviews

Stunning Guest House 15 min. from Zoo, Downtown

Stunning guest house that's 15 minutes to San Diego Zoo + downtown San Diego. The cottage is decorated with mid-century and one-of-a kind furniture in a comfy living space overlooking a gorgeous garden. Enjoy the the garden on your private deck, watch TV while relaxing in the handcrafted Nicaraguan rocker or 1950s Danish slipper chair. The cottage also has a comfy queen-sized bed and a full kitchen that's stocked with what you'd need. Oh, and all guests arrive to a homemade loaf of bread.

Guest favorite

Guesthouse in La Mesa

5 out of 5 average rating, 214 reviews

SDCannaBnB #1 *420 *parking *dog-friendly *hot tub

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental! Our casita is newly remodeled with luxury ammenities. We proudly cater to the cannabis community and non-users alike. Our casita has HEPA air purifiers, is fully ventilated and receives deep cleanings between each guest. This ensures that every guest checks into a clean, fresh-smelling place that feels like home. Our casita is located in our quiet, fully fenced in backyard, close to San Diego's attractions

Guest favorite

Guesthouse in El Cajon

4.96 out of 5 average rating, 103 reviews

Farmhouse Cottage Retreat with Mountain View’s

Welcome to the Farmhouse Studio Cottage located in the foothills of San Diego County. Formerly a horse and cattle ranch now transformed into a park like setting. See beautiful views as you drive down the tree lined inner roads of the property. Hear birds as you awake in the morning and an occasional rooster off in the distance. Get back to nature at this lovingly appointed studio hideaway. Pet friendly, please describe pets prior to booking. Pet fee of $60.00 per pet per stay.

Guest favorite

Guesthouse in El Cajon

4.98 out of 5 average rating, 205 reviews

Fletcher Hills - modern 1 BR.Easy, no step access.

** 48 hours between check-ins. Thorough cleaning and sanitizing.. Four night minimum stay. Dogs ONLY are welcomed on a case by case basis. They must be house trained and are not permitted on any furniture. If you instant book, you must contact me about your pet within 24 hours. Smoking is permitted in the outside areas - patio, gazebo, yard. Easy freeway access helps any commute to downtown and area attractions. Having your own vehicle is the best way to get around..

Guest favorite

Guesthouse in Jamul

4.95 out of 5 average rating, 186 reviews

Retreat house. Nature, Hot Tub, Views!

Expansive spaces, ocean views, birds singing, and larger than life granite boulders all come together to offer something that feels like magic. More like a national park than a home, we've found that guests enjoy the pace and peaceful surroundings and spend most of their visit without leaving. That being said, if you're feeling more exploratory, there are many options within a short drive including hiking, wine tasting, horseback riding, fishing, and even sky-diving.

Guest favorite

Guesthouse in Dulzura

4.97 out of 5 average rating, 605 reviews

Vineyard & Winery Guest House

A hidden gem! Get away and stay at the historic pioneer era Clark Ranch established in 1885. Our guest house sits above our winery tasting room and has its own private entrance and driveway. It's clean, cozy, and self-contained . Make it a weekend 'getaway' stay and sample our fine wines , and Estate Olive Oil. There is a tower in the vineyard where you can enjoy a glass of wine and watch the sun set. Balcony overlooks Dulzura Creek.

Guest favorite

Guesthouse in La Mesa

4.9 out of 5 average rating, 167 reviews

La Cabana

Perfect getaway for the wandering individual, couple, or young family. This rustic casita is surrounded by beautiful mountain and ocean views! Enjoy swimming in the pool, stargazing, lounging, or casual day trips around San Diego (All the amenities are shared with the main house) . The casita has one queen bed and a sofa bed, small kitchenette. Plenty of parking in driveway. Please read entire listing for details.

Guest favorite

Guesthouse in Chula Vista

4.95 out of 5 average rating, 518 reviews

Private Casita in Great Eastlake Neighborhood

This room is a "casita" (seperate living space) away from the house. It has a private entrance with a cypher lock on the door. The room has new carpet, new tile, and queen size bed. The Eastlake neighborhood is very safe and very quiet. We are located about 20 mins from the beach, downtown San Diego, and San Diego international airport. This location is only 2 miles from the Otay Ranch Mall.