Guesthouse holiday rentals in East County, San Diego

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Top-rated Guesthouses in East County, San Diego

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

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Top Guest favourite

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

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!

LocationFamilyBeach

4.91 out of 5 average rating, 476 reviews

Top Guest favourite

The vibrant sunset sky is filled with hues of pink, orange, and purple, reflecting beautifully in the calm water of the pool. Palm trees stand in silhouette, framing the picturesque view of the surrounding mountains and valleys.

Guesthouse in Jamul

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

LocationValuePets

4.98 out of 5 average rating, 115 reviews

Top Guest favourite

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

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.

FamilyValueHiking

4.99 out of 5 average rating, 231 reviews

Top Guest favourite

A bright living area is visible, featuring a mix of modern furnishings including a cozy sofa, a smart TV, and a circular dining table with wooden chairs. Large windows allow natural light to fill the space, highlighting the warm wooden flooring and inviting decor.

Guesthouse in La Mesa

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

ValueLocationView

4.98 out of 5 average rating, 133 reviews

Top Guest favourite

The tiny cabin is illuminated by soft lighting, showcasing its wooden exterior and welcoming design. Surrounding cacti and plants enhance the natural setting, while steps lead up to a private deck. The evening sky provides a serene backdrop, highlighting the cabin's cozy atmosphere.

Guesthouse in Spring Valley

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

Tucked into a quiet canyon oasis above San Diego, CA, this very private, nature-immersed retreat is located just 20 min from downtown San Diego ✦Private Hot Soaking Tub under the stars ✦Panoramic City views (west facing) ✦Custom outdoor movie theatre ✦Exclusive amenities - just for you! ✦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"!

ValueLocationAmenities

4.98 out of 5 average rating, 232 reviews

Top Guest favourite

The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.

Guesthouse in La Mesa

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.

ValueFamilyTV

4.96 out of 5 average rating, 180 reviews

Top Guest favourite

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

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.

ValueLocationPets

4.95 out of 5 average rating, 242 reviews

Top Guest favourite

A child sits quietly on a wooden dock overlooking a calm lake. A sign indicating 'Catch & Release' is visible beside the child, and the surrounding hills are adorned with autumn foliage reflecting in the water, creating a serene and peaceful environment.

Guesthouse in Descanso

Private Lake with fishing/Tennis court near Julian

This 2 bedroom home is in a private setting that requires gate access. The lake has fish for those looking to fish in a serene setting . In the brilliant summer sunshine the lake has a perfect mirror for the mountains that surround it. You will have usage of our community kayaks and paddle boat that can take you to the lake island. The home has a full kitchen ,Wifi, forced air ,fireplace heater and air conditioner. Come and enjoy this unique paradise. Sorry no pets

LocationFamilyView

4.95 out of 5 average rating, 258 reviews

Top Guest favourite

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

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.

LocationFamilyHeating

4.96 out of 5 average rating, 275 reviews

Guest favourite

A cozy living space is furnished with a dark leather sofa facing a coffee table. A dining area, equipped with a wooden table and four chairs, is visible. Light-colored walls are complemented by plantation shutters and two art pieces, while a ceiling fan hangs overhead.

Guesthouse in Alpine

Gorgeous Guest Home

NEWER 1 bed/1bath guest home located in beautiful Alpine. Includes a fully furnished living space, equipped kitchenette, Two Smart TVs, and WIFI. Extra large room with a super comfy Queen size bed. Full size bathroom with washer and dryer. Unit has A/C and heat. Parking is located on property. Wonderful neighbors and neighborhood. The entrance is completely private. Minutes to Viejas or the Sky Falconry. 🦅

LocationNearbyGetting around

4.98 out of 5 average rating, 124 reviews

Top Guest favourite

An open concept studio loft is depicted, featuring a light-filled living space. A comfortable sofa is positioned in the foreground, with a sliding barn door leading to a kitchenette and laundry area. Natural light streams through a large window, brightening the entire room.

Guesthouse in El Cajon

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.

FamilyLocationAccuracy

4.97 out of 5 average rating, 226 reviews

Superhost

A spacious bedroom features a large king size bed with a textured blanket, complemented by a nightstand and a decorative lamp. Sliding glass doors open to a deck, allowing natural light to fill the room. A flat-screen TV and a desk are visible in the background.

Guesthouse in Normal Heights

Mountain View Retreat in Gated Estate (Hot Tub)

Perched above a canyon with spectacular panoramic mountain views, this private guest house is a secluded retreat in one of San Diego’s most eclectic and desirable neighborhoods less than 6 miles from the Downtown San Diego airport. Enjoy a fully equipped kitchen, luxe king size bed and dual sliding glass doors that open to an expansive deck with patio seating, private hot tub and BBQ area.

LocationValueSleep quality

4.99 out of 5 average rating, 492 reviews