Guesthouse vacation rentals in East County, San Diego

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Top-rated guesthouse rentals in East County, San Diego

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

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Top guest favorite

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.

Guesthouse in San Diego

5 out of 5 average rating, 210 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!

Superhost

A scenic view captures lush hillsides and a calm lake under a clear sky, with a rainbow arching gracefully over the landscape. Green vegetation sprawls across the area, adding vibrancy to the tranquil scene.

Guesthouse in Escondido

4.91 out of 5 average rating, 789 reviews

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you will feel like you're a million miles away from everything as you take in the views from the cabin, deck or the outside shower, swim in the saltwater pool, or relax by the fire bowl. A short walk to lake with boating, fishing & miles of hiking/mountain biking trails. Property offers swimming pool, fire bowl, and shaded arbor. SD Zoo Safari Park, wineries, breweries, & ocean beaches all within easy reach.

Top guest favorite

Guesthouse in Spring Valley

4.99 out of 5 average rating, 383 reviews

Mountaintop View• SoakTub• Cinema • Zoo pkg add-on

City skyline and sunset views from this 600 sq ft private cottage—just a short drive outside the city, in the foothills of San Diego. Located on a gated estate overlooking 30 acres of canyonland, it features a cozy Queen bed, 50” Smart TV, Wi-Fi, kitchen, A/C & heat Unwind in the outdoor hot soaking tub with breathtaking views, catch a movie under the stars, and spot wild peacocks roaming the grounds. On select nights, enjoy SeaWorld fireworks lighting up the skyline, a truly unforgettable stay

Top guest favorite

Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.

Guesthouse in La Mesa

4.99 out of 5 average rating, 131 reviews

Private 1 BR Paradise retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

Guest favorite

A spacious deck is visible, furnished with a table and four wicker chairs. A decorative bowl sits at the center of the table. The panoramic view of the surrounding landscape and city skyline stretches into the distance under a clear blue sky.

Guesthouse in La Mesa

4.97 out of 5 average rating, 215 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.

Superhost

The exterior of a historic stone cottage showcases a rounded structure with large, circular windows. Native plants and decorative rocks surround the entrance, highlighting the natural landscape. The name 'Anna' is displayed on a rustic wooden sign, further enhancing the cottage's character.

Guesthouse in La Mesa

4.89 out of 5 average rating, 384 reviews

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!

Top guest favorite

A green, manicured lawn is highlighted with a white gazebo and ornamental garden seating. Towering palm trees flank the scene, while a staircase leads up to a spacious home nestled in the background. Shadows create a gentle pattern on the grass from surrounding elements.

Guesthouse in Escondido

5 out of 5 average rating, 166 reviews

Infinity Poolside Apt. In San Diego Wine Country

162 Perfect 5.0 Reviews-Amazing views, peaceful and beautiful space in a wine country setting. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of wine country, lake, golf course and mountains on the 14th green of a golf course with full access to the estate pool, spa, covered parking, EV charger w/private European park. Large luxury suite with a Kitchen, Sitting Room, Bathroom, Steam shower/Sauna and bedroom with luxurious robes, linens and towels.

Top guest favorite

A welcoming entrance features a textured walkway leading to a front door, framed by a wooden railing. Colorful flowers bloom along the sloped landscape, enhancing the natural appeal of the surroundings. Clear skies and distant homes provide a serene backdrop.

Guesthouse in El Cajon

4.99 out of 5 average rating, 198 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.

Top guest favorite

An Airstream is positioned on a hillside, surrounded by lush greenery and desert plants. Lounge chairs and a shaded patio area are visible, providing a space for relaxation. The backdrop features rolling hills under a clear sky, highlighting a peaceful and private setting.

Guesthouse in Spring Valley

4.98 out of 5 average rating, 390 reviews

Nature Escape•View•Sauna•SoakTub• Zoo pkg add-on

Nestled in a quiet canyon just a short drive outside the city, this Airstream glamping retreat offers incredible panoramic city skyline, sunset & nature views. Modern comforts include A/C, a full kitchen, fast Wi-Fi, and convenient off-street parking on a gated estate Cozy up by the firepit as the city sparkles below or try your swing at the golf tee. Reconnect & recharge with your own outdoor hot soaking tub, open-air rain shower, and wood-fired sauna - the perfect retreat for nature lovers!

Guest favorite

A modern loft space features warm wood flooring and a plush area rug. A gray sofa faces a sleek entertainment center. A desk and stool are situated by a window, offering views of the surrounding landscape. Natural light fills the room through large windows.

Guesthouse in La Mesa

4.95 out of 5 average rating, 193 reviews

Mountain top view getaway loft

This loft is completely sound proof! VIEWS, VIEWS, VIEWS!! Do not miss this stunning contemporary loft, located in the highly desired Mt. Helix community. The guest house faces west, giving you phenomenal 270-degree views of the ocean, Downtown, Point Loma, Coronado islands, Coronado bridge, and more! Designed and built by an acclaimed San Diego home designer, this property was featured in Dream Homes Magazine and is well known for its incredible design and construction.

Top guest favorite

A spacious living area is equipped with a plush sofa and light-colored chairs, accented by decorative pillows. A wooden coffee table rests on a colorful area rug. Natural light fills the room through two windows, highlighting a work desk and welcoming artwork on the wall.

Guesthouse in El Cajon

4.98 out of 5 average rating, 231 reviews

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

** 36 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..

Top guest favorite

A stunning sunset is captured over a serene landscape, with the sun dipping below the horizon. Soft hues of orange and pink dominate the sky, reflecting on the water's surface. In the distance, the outline of an island is visible against the ocean.

Guesthouse in Jamul

4.95 out of 5 average rating, 232 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.