Guesthouse vacation rentals in San Diego County

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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, 466 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
Guesthouse in Spring Valley
4.99 out of 5 average rating, 425 reviews

Casita•Views•Outdoor Cinema• SoakTub+Zoo add-on

Escape to a private canyon retreat overlooking 30 acres of scenic hillsides just 20 minutes from Downtown San Diego, CA ✦ Private Hot Soaking Tub ✦ Outdoor Movie Theater ✦ Panoramic Sunset & City Views (west facing) ✦ Entire casita - no shared walls, or above/below units ✦ Exclusive amenities - just for you! ✦ Fast Wi-Fi ✦ 50" Smart TV ✦ Quiet A/C & Heat ✦ Private Patio ✦ Gated offstreet parking A perfect retreat for those wanting a special getaway on a very unique property overlooking the city

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!

Top guest favorite
Guesthouse in Spring Valley
4.98 out of 5 average rating, 442 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

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.

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.

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.

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, 234 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 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.

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.

Superhost
A welcoming front porch features two chairs facing a lush green lawn. The vibrant sunset sky adds a warm glow, while surrounding greenery provides a touch of privacy. The entrance is enhanced by a bright green door and decorative elements above.
Guesthouse in Ocean Beach
4.9 out of 5 average rating, 136 reviews

OB Casita

Stay in a cozy Casita surrounded by a private garden. The inside space is petite, the yard is large. This in-law unit features a kitchenette, a private bathroom, a BBQ, and a fenced outdoor area perfect for pups! Sit under the avocado tree on the back deck and watch for the OB parrots. Or, take a short walk in this lively neighborhood to, beaches, dog beach, tennis courts, restaurants, bars, shopping, a playground, or a dog park.

Top guest favorite
An outdoor terrace features a spacious seating area with plush cushions, a central firepit, and lounge chairs overlooking a panoramic view of the landscape and ocean in the distance. The setting invites relaxation and enjoyment in a serene environment.
Guesthouse in Pacific Beach
4.95 out of 5 average rating, 120 reviews

Beach views for 2! Jacuzzi, fire pit

This mid-century modern jewel offers one of the best views in San Diego while still being walking distance (9 blocks) to the beach. You'll get a 1 bedroom with queen bed, full kitchen, living room with a futon couch (suitable for only one adult or two kids). I live upstairs and have a deck so you get your own private deck below me with a firepit and jacuzzi. Perfect place for a couple (or possibly a family with 2 small children).

Popular amenities for San Diego County guesthouse rentals

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