Guesthouse vacation rentals in San Francisco Peninsula

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Top-rated guesthouse rentals in San Francisco Peninsula

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

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Top guest favorite
A charming guest house entrance is framed by lush greenery and paths made of red bricks. The door, adorned with a decorative pergola, features a sleek black finish. The surrounding plants create a serene environment, inviting guests to enjoy the natural beauty.
Guesthouse in Palo Alto
4.93 out of 5 average rating, 239 reviews

Downtown Palo Alto Gem! Cute, Spotless Guest House

We invite you to stay in our private, remodeled guest house. It's an easy walk to the restaurants and shops on University Avenue, in a safe and sought-after neighborhood in Downtown Palo Alto. The guest house was recently renovated and has a gorgeous bay window, air conditioning, two skylights, and a spa-like bathroom. We pride ourselves in keeping it absolutely spotless. The studio cottage is 200 square feet. It’s perfect for a single person but has a queen bed, so can accommodate a couple

Top guest favorite
A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.
Guesthouse in Woodside
4.99 out of 5 average rating, 363 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
A cozy, dark green cabin is nestled among towering trees, showcasing a large window and a glass-paneled door. Three steps lead to the entrance, surrounded by a natural landscape of redwoods.
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
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 area is framed by wooden fencing, featuring various plants and greenery. A door with a purple frame leads into the guesthouse. The wooden deck enhances the natural setting, contributing to a sense of tranquility and seclusion.
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, 358 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.

Guest favorite
Guesthouse in Walnut Creek
4.96 out of 5 average rating, 137 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Top guest favorite
The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.
Guesthouse in Oakland
4.92 out of 5 average rating, 401 reviews

Guesthouse Garden Retreat

Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

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, 126 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
The interior of the studio features bamboo flooring, with a spacious bed framed by warm wood tones. A small dining table with wooden chairs is present, while a white dresser and a vase of flowers enhance the decor. Light streams in through a window with gray curtains.
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 Woodside
4.99 out of 5 average rating, 585 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

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