Guesthouse vacation rentals in San Mateo County

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Top-rated guesthouse rentals in San Mateo County

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

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 300 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 309 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.

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 654 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Guest favorite

Guesthouse in Half Moon Bay

4.82 out of 5 average rating, 478 reviews

Cozy beach bungalow near harbor & coastal trails

Beach cottage in village of El Granada w/ocean view from property. Walk to Surfer’s beach, 2-minute drive to harbor. Bike or stroll on the paved coastal bluff trail. Kayak in the harbor. Hiking in the hills behind the cottage in Quarry Park. Full kitchen. Attached covered deck. Cable TV & WIFI. Queen size memory foam bed. Sit around the outdoor firepit at night-see the stars & hear the ocean waves. Boat harbor nearby with seafood restaurants, brew pubs & live music. 3 miles drive to Main St.

Guest favorite

Guesthouse in Redwood City

4.96 out of 5 average rating, 116 reviews

Fabulous Private Suite - Comfortable & Elegant

Entire Guest House - Bright, clean, comfortable, elegant and recently remodeled bathroom, private entrance and free parking in the heart of Silicon Valley. Great location: a 10-minute walk to Key Market (Grocery) and convenient stores; just a mile to Downtown Redwood City, Sequoia Plaza, Wholefoods, Restaurants, Movie Theaters, and Redwood City Cal Train Station for quick trips to San Francisco and other Peninsula cities. A 15-minute drive to Stanford and Hillsdale Shopping Malls…

Superhost

Guesthouse in Palo Alto

4.84 out of 5 average rating, 122 reviews

Cozy Professorville Cottage

Experience old Palo Alto in this cozy cottage. Nestled in the the heart of Professorville, this 1903 studio is full of charm. Just a quick walk to Downtown Palo Alto and a short walk/bike to Stanford University. Walk time to common destinations: University Avenue/Downtown - 5-10 min walk Town & Country Village (restaurants/shops) - 10 min walk Stanford Campus - 20-30 min walk, or longer (depending on campus destination) Caltrain Station - 10 min walk Whole Foods Market - 5 min walk

Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 210 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.

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 158 reviews

Cozy Studio 1B/1B w A/C No Pet in San Mateo

This cozy studio is good for a couple vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 412 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 515 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.

Guest favorite

Guesthouse in San Mateo

4.93 out of 5 average rating, 213 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 874 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.