Guesthouse holiday rentals in East County, San Diego

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in East County, San Diego

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Descanso

4.95 out of 5 average rating, 250 reviews

Romantic Retreat & Private Fishing near Julian

Come and stay at this recently renovated little casita with surrounding wildlife. Get away from the busy city life and relax in nature. This semi -private lake is like no other, you have access to our community kayaks,paddleboat and fishing is also great here. In the mornings or mid day you can get a glimpse of blue jays,doves, turkeys and deer. This casita is perfect for a romantic getaway or for a small family to spend some quality time . Come and enjoy nature! WIFI NOW IN UNIT! No pets

Guest favourite

Guesthouse in El Cajon

4.99 out of 5 average rating, 153 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 favourite

Guesthouse in La Mesa

4.92 out of 5 average rating, 208 reviews

Fig Tree Bungalow

Enjoy your stay in San Diego in this newly renovated guesthouse. Centrally located about a mile from Hwy 8, Hwy 125, and the Grossmont Trolley Station & Transit Center. Only a 15-20 minute drive to downtown, the airport, the beaches, and most of San Diego's other popular tourist attractions. This cozy, two-story, detached unit is located behind my home, and has its own private entrance and partitioned yard for your enjoyment. There's plenty of street parking directly in front of the house.

Guest favourite

Guesthouse in La Mesa

4.99 out of 5 average rating, 172 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 favourite

Guesthouse in Lemon Grove

4.97 out of 5 average rating, 119 reviews

Adorable Lemon Grove Studio

Enjoy your stay at our recently updated/remodeled cozy studio with all the comforts. We are 15 minutes from downtown San Diego, our city's beautiful beaches, Mexico, and 30 minutes to the mountains. We are located between 2 trolley stations and a 2 minute drive to access the freeway. The studio includes a separate sleeping area with a comfy queen bed. The sleeping area and living area are separate areas. Enjoy our updated kitchenette for your meals. The studio has a private entrance.

Guest favourite

Guesthouse in El Cajon

4.98 out of 5 average rating, 191 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 favourite

Guesthouse in El Cajon

4.93 out of 5 average rating, 165 reviews

San Diego Bohemian Poolside Lounge @ Eden East

Retreat to a private 1 bedroom poolside apartment. Not just a place to stay, but a retreat to recharge mind, body & spirit and forget everything currently happening on the "outside". Perfect escape for locals and tourists alike...ideal for spending some time with friends and loved ones soaking up the chill vibes of our little hidden gem in the East County of San Diego. Strong WIFI. Shared pool. By reserving, we assume you've read entire ad and agree to all house rules.

Guest favourite

Guesthouse in La Mesa

4.99 out of 5 average rating, 133 reviews

Stunning Guest House 15 min. from Zoo, Downtown

Stunning guest house that's 15 minutes to San Diego Zoo + downtown San Diego and 18 minutes to a beach. Unique private property with mid-century and one-of-a kind furniture in a comfortable living space. Enjoy IPAs on your private deck or coffee in bright Fiesta cups, watch TV while leaning back in the handcrafted Nicaraguan rocker or the 1950s Danish slipper chair. The cottage also has a comfy queen-sized bed. Like eclectic? This place exudes it.

Guest favourite

Guesthouse in Dulzura

4.97 out of 5 average rating, 579 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 favourite

Guesthouse in Alpine

4.98 out of 5 average rating, 311 reviews

La Casita Private Resort Spa and Mini Golf Course

We welcome all races, nationalities, cultures and fur babies. Perfect place for a long term stay. We take extra care to disinfect frequently touched surfaces between reservations. Smoking is permitted outside only. We welcome your well behaved fur babies. Max 3, Boarding $30 a day for each fur baby paid directly to host. Private, secluded Jacuzzi. Daily use fee $30 paid directly to host.

Guest favourite

Guesthouse in Chula Vista

4.95 out of 5 average rating, 476 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.

Guest favourite

Guesthouse in Lakeside

4.94 out of 5 average rating, 103 reviews

Sky Mesa-Adorable Cottage on the Hill

Sky Mesa is a lovely space to unwind and relax after a busy day. Awake refreshed and ready for a day of exploring San Diego County in this quaint, sunny cottage with impressive views. Head out and wander east to the mountains and desert, or west to the many beautiful beaches. After a day of fun, grab a glass of wine, soak in the jacuzzi and look out over the Cuyamaca Mountains.