Guesthouse vacation rentals in San Diego County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in San Diego County

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

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Top guest favorite

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

4.91 out of 5 average rating, 465 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!

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Top guest favorite

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

4.98 out of 5 average rating, 127 reviews

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!

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Top guest favorite

Guesthouse in Spring Valley

4.98 out of 5 average rating, 441 reviews

Airstream•Sauna•SoakTub• Views•Firepit+Zoo add-on

Just 20 minutes from San Diego's most iconic attractions, yet seemingly a world away, this classic Airstream overlooks 30 acres of native California chapparal, wild sage and California pepper trees with sweeping city and sunset views Designed as a private nature retreat, it invites you to slow down, reconnect, and recharge. Soak beneath the stars, unwind in the handcrafted wood-fired redwood sauna, refresh under the open-air rain shower, and gather around the fire as city lights twinkle below

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Top guest favorite

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

4.97 out of 5 average rating, 173 reviews

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.

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Top guest favorite

A spacious living area features a large sectional sofa adorned with decorative pillows, complemented by a wooden coffee table. A vibrant wall art piece with colorful surfboards is displayed above the couch, while natural light fills the room through expansive windows.

Guesthouse in Mission Hills

4.97 out of 5 average rating, 297 reviews

Beautiful Historic Home and Gardens Near Downtown!

Location, Location, Location...Welcome to Union Street Gardens. We are dedicated to providing a peaceful, serene atmosphere in which our guests can relax after a long day of exploring beautiful, sunny San Diego. This unique historic craftsman bungalow is just minutes from downtown, Balboa Park, the Zoo, beaches, and includes a Chef's kitchen, outdoor deck, gardens, fire pit and spa! Perfect for a family of 4 or two couples. Sorry no parties or large groups and no external guests please.

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Top guest favorite

The exterior of a two-story guest house is illuminated in warm light, showcasing a balcony with railing that overlooks the surrounding greenery. A welcoming entrance is framed by well-kept garden areas, with steps leading up to the house.

Guesthouse in Dulzura

4.97 out of 5 average rating, 630 reviews

Vineyard & Winery Guest House

A hidden gem! Please send an inquiry if you are interested in staying with us. 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. There is a tower in the vineyard where you can enjoy a glass of wine and watch the sun set. Balcony overlooks Dulzura Creek.

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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, 233 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.

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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

4.96 out of 5 average rating, 268 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.

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Top guest favorite

A spacious sleeping area features a bed adorned with floral-patterned bedding. Two lamps are positioned on bedside tables, providing soft light. A wooden bench sits at the foot of the bed. Large glass doors lead to a lush garden, enhancing natural light in the room.

Guesthouse in Leucadia

4.97 out of 5 average rating, 789 reviews

Beach City Bungalow

Detached 400 sf studio with full kitchen, private redwood deck, and own entrance/parking. Just a mile to the coast, the house is a 15-20 minute walk to the beach and a 25-minute walk into Encinitas, a classic beach surf town. Restaurants, live music, and quaint shops line nearby Highway 101. The large tropical garden has walking paths and seating areas perfect to relax in. The property is a true oasis! City of Encinitas business license #RNTL-007530-2017.

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Top guest favorite

A spacious outdoor deck features comfortable seating arrangements with light-colored cushions, providing a relaxed space for guests. A wooden coffee table sits in the center, surrounded by potted plants and the entrance to the guest house visible in the background.

Guesthouse in San Diego

4.98 out of 5 average rating, 437 reviews

*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!

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Top guest favorite

The exterior of the barn is shown, featuring a clean white facade with a sloped roof. A sizable driveway leads to a garage with multiple doors. Lush greenery surrounds the building, contributing to a serene environment.

Guesthouse in Vista

4.99 out of 5 average rating, 361 reviews

New Tranquil Barn Retreat on a Peaceful Half Acre

The Buena Vista barn is a clean, quiet, and upgraded detached barn in Vista with everything you need for a peaceful and comfortable stay! Only 10 minutes to downtown Vista, you'll find great restaurants, breweries, shops, and a movie theater. Points of interest: • Downtown Vista: 10 minutes • Cal State San Marcos: 15-17 minutes • Beach: 20 minutes • Legoland: 22 minutes • Temecula and Wine Tasting: 30-40 minutes • Sea World: 47 minutes

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Top guest favorite

The exterior of a charming casita is highlighted with a terracotta tile roof and earthy stucco walls. Lush greenery surrounds the property, with stone pathways leading to the entry. A tall palm tree stands prominently against the clear blue sky.

Guesthouse in Escondido

4.98 out of 5 average rating, 131 reviews

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.

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