Guesthouse vacation rentals in San Francisco Peninsula

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in San Francisco Peninsula

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

1 of 1 pages1 / 1
Top guest favorite
A wooden deck is nestled among tall redwood trees, featuring two swings adorned with lighting overhead. The warm glow of string lights creates a cozy atmosphere, while the natural wood grain of the deck enhances the rustic charm of the setting.
Guesthouse in Woodside
4.99 out of 5 average rating, 364 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Top guest favorite
Guesthouse in Felton
4.99 out of 5 average rating, 308 reviews

Cozy Coastal Redwood Cabin

Rest and connect in this warm, cozy, and private cabin that is nestled in the redwoods. Only minutes away from Henry Cowell State Park, where you can enjoy world class mountain biking trails, hiking, or swimming in the river. Or, enjoy the beach 15 minutes away. This is a perfect place to refresh in the magic of the Coastal Redwoods. Music fills most nights either from the Felton Music Hall or from the chorus of frogs. And wake up in the mornings to the mist in the trees when the fog rolls in.

Top guest favorite
Guesthouse in Redwood City
4.99 out of 5 average rating, 124 reviews

Private Cottage near Redwood City and San Carlos Downtowns

Quiet, private two-level garden cottage ideal for business travelers and visiting family. Gig+ high-speed Wi-Fi, workspace, central AC & heat, king-size bed, private entry (24/7), 50” 4K TV, fully equipped kitchen with granite countertops, and guest-exclusive washer and dryer. Bedroom, living area, kitchen, bathroom, and dining / work space. Shared garden with BBQ, teak table and hot tub. Walkable to transit, downtown areas, and a popular breakfast café. Some train and light traffic noise.

Guest favorite
A sunset casts vibrant orange and purple hues across the sky, reflecting on the ocean's surface. Waves gently lap against a sandy shore, where several birds can be seen near the water's edge. A distant lighthouse is visible on the horizon.
Guesthouse in Half Moon Bay
4.92 out of 5 average rating, 486 reviews

Stylish Seaside Cottage - Walking to Beach

A perfect place for romantic getaways! newly built on top of our detached garage, 10mins walk to beach! private entrance, smart lock, modern skylights, quality linens, trendy decor, private deck with splendid ocean view, on-site parking! At the sunny beautiful El Granada, 4miles north of Half Moon Bay, a lot of fun activities: spending your days on the beach, exploring the hiking trails, trying out many local restaurants, or road trip along Highway 1, 30 mins to SF or 60 mins to Santa Cruz.

Top guest favorite
A patio area is surrounded by tall redwood trees, featuring a grill and outdoor seating arrangement. Colorful plants and flowers enhance the natural setting, while a fenced yard creates a sense of privacy. The cabin’s exterior is visible, with a decorative wall accent.
Guesthouse in Woodside
4.98 out of 5 average rating, 474 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those inclined toward an active lifestyle, we are close to Purisima Creek, Huddart Park, and the El Corte de Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space)Note 20 minutes from Half Moon Bay with beautiful beaches and 30 min from Stanford in Palo Alto. We are adjacent to The Mountain House Restaurant. (note) The bed is a Murphy bed in the living area. NO PETS!

Guest favorite
A private garden space is enclosed by wooden fencing, featuring various plants and greenery. Steps lead down to a lower level, where a darker area includes more foliage. Soft lighting illuminates sections of the garden, enhancing the tranquil atmosphere.
Guesthouse in Oakland
4.8 out of 5 average rating, 1,032 reviews

The Purple Door, Private Sanctuary, Epic View

Private guesthouse located in the Oakland Hills with stunning views of the bay. We recognize the importance of privacy, this guesthouse will allow you to have everything you need all while never having to be bothered. The sunset views can be taken in from your bed or the deck. There is a bus stop about 150 yards away if you need, the airport is about a 7 minute ride away, rail (BART) is about 5 minutes and the house is near a freeway for quick access to everywhere in the Bay Area.

Top guest favorite
Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.
Guesthouse in Woodside
4.97 out of 5 average rating, 359 reviews

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Top guest favorite
A spacious deck features two wooden directors' chairs positioned around a small circular table. Lush greenery lines the perimeter, creating a natural backdrop. A sunshade is partially visible, offering protection from the sunlight.
Guesthouse in San Carlos
4.99 out of 5 average rating, 143 reviews

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

Top guest favorite
A serene beach scene at sunset is captured, featuring gentle waves reflecting the hues of orange and blue in the sky. Silhouettes of people can be seen walking along the shoreline, while lights from the distant marina twinkle against the darkening landscape.
Guesthouse in El Granada
4.97 out of 5 average rating, 127 reviews

Coastal Cottage Guest House

Guest house is attached to our primary residence but has a separate exterior entrance. The interior is separated by double doors that lock from both sides, similar to adjoining hotel rooms. The backyard is shared by us, the owners. There’s a very real chance you’ll be greeted by our friendly Australian Shepherd, Gracie, during your stay! You may see us in the yard during your stay. Feel free to say hi! Otherwise, we like to give our guests privacy.

Top guest favorite
Guesthouse in Lagunitas
4.99 out of 5 average rating, 231 reviews

Comfy Studio Near Trails and Beaches

Comfy and private freestanding studio with large deck. The studio is nestled in a grove of live oaks, and overlooks a quaint market flower garden. This is a bed and breakfast, offering coffee, tea, fresh fruit, oatmeal, granola, juice, milk, oat/almond milk etc. This fenced-in property, and large, private, covered deck provides safe storage for guest bikes and sporting equipment. Local trail maps provided for your hiking and biking adventures!

Top guest favorite
Guesthouse in Portola Valley
4.94 out of 5 average rating, 222 reviews

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

Top guest favorite
A white trellis adorned with vibrant flowers stands against a sunny garden backdrop. A mix of colorful blooms, including tulips and daisies, creates a lively display in a brick planter, inviting guests to enjoy the natural beauty of the surroundings.
Guesthouse in Atherton
5 out of 5 average rating, 236 reviews

Charming Studio Garden Cottage near Stanford

Come and relax in our light and airy studio cottage situated in a beautiful garden setting, the perfect get-away after a day of business meetings or visiting with family. We are close to major Silicon Valley destinations as well as Stanford Hospital, 45 minutes' drive from San Francisco, San Jose and the beach in Half Moon Bay — easy access to Highways 101 and 280. Our quiet neighborhood full of mature oak trees beckons you to take a walk.

Popular amenities for San Francisco Peninsula guesthouse rentals

Destinations to explore