Vacation rentals in San Mateo County

4.99 out of 5 average rating, 715 reviews

Guesthouse in San Carlos

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.

4.99 out of 5 average rating, 174 reviews

Camper/RV in La Honda

40 Acre Redwood Forest With Private Trails

We are the descendants of an old San Mateo County pioneer family. We have been passed down and live on a 40 acre redwood forest, backed by 1000 acres of parkland. We would like to share our forest with you. Take a walk and learn of the history behind La Honda's Woodwardia Lodge built in 1913. Walk on private 150 year old logging trails at this historic getaway. Enjoy the natural beauty of the surrounding Redwood forest. Cozy up in a 40' New 2024 RV. All proceeds go to restoring WJS Log Cabin.

4.97 out of 5 average rating, 267 reviews

Guesthouse in Woodside

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.

Home in South San Francisco

4.97 out of 5 average rating, 123 reviews

Stylish & Serene Home - Private Unit!

Discover our chic and contemporary 1-bed, 1-bath house in South San Francisco! Recently renovated, it offers a comfortable queen-size bed for a restful stay. Relax with the 55" TV (HBO Max) after exploring, and enjoy your own kitchen for home-cooked meals or our top restaurant recommendations. Conveniently near SFO / transportation hubs and not far from the city, this is your ideal base to explore the Bay Area. We look forward to hosting your comfortable and convenient stay!

4.93 out of 5 average rating, 246 reviews

Guest suite in San Mateo

Luxury King Bed & Spa Bathroom

Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, microwave and a Keurig coffee maker. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

4.97 out of 5 average rating, 466 reviews

Guesthouse in Pacifica

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

4.9 out of 5 average rating, 169 reviews

Guest suite in San Bruno

Hello Kitty Guesthouse in SB

Newly renovated guesthouse with its own entrance, full bath, kitchenette with new microwave and refrigerator. The owner is a huge Hello Kitty addict so you will see a Hello Kitty plush wall along with Sanrio character art decors in the house. If you’re also a Sanrio Hello Kitty fan, you will love this cute guesthouse! The owner has carefully curated these art pieces. You are not allowed to remove anything from the unit.

4.95 out of 5 average rating, 438 reviews

Guesthouse in La Honda

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.

Camper/RV in Half Moon Bay

4.98 out of 5 average rating, 126 reviews

Airstream Beach View (Dream) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Surf views with large windows. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, A/C and fully stocked kitchen. Full bathroom with shower. If this one is booked, there are three other equally similar Airstreams on the property.

4.93 out of 5 average rating, 225 reviews

Guesthouse in San Mateo

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. *

4.94 out of 5 average rating, 142 reviews

Guest suite in San Bruno

Stylish Private Guest Suite Near SF and SFO

Welcome to our stylish Guest Suite! This modern retreat is perfectly situated near San Francisco and SFO, offering you convenience and comfort. With thoughtfully designed interiors, a comfortable bed, and amenities to enhance your stay. Conveniently located 10 min drive from SFO Airport and 15 min drive from San Francisco.

Guesthouse in Redwood City

4.96 out of 5 average rating, 118 reviews

Beautiful NEW private guest studio

Clean, new construction guest studio with private entrance centrally located in a residential neighborhood near downtown Redwood City. Queen bed with full bathroom, A/C, and fridge/coffee/microwave. Small desk next to bed great for remote work or studies. Easy self check-in with smart lock and easy parking.

Vacation rentals for every style

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Popular amenities for San Mateo County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in San Mateo County

4.9 out of 5 average rating, 152 reviews

Home in Montara

Ocean Mountain View Home - Walk to Trails Beach

JulieRating, 5 stars3 weeks ago

Beautiful property with plenty of room. Open concept living area was terrific. The back deck and fire pit below were a big hit with the family. Puzzles & games galore. My granddaughter and I enjoyed the Ping Pong Table. Host was communicative and responded to any question. I would definitely come back and tell a friend. Perfect getaway!

4.9 out of 5 average rating, 106 reviews

TreeTops OceanView Retreat_HotTub_Month/LongTermOk

KathrynRating, 5 stars4 months ago

Had a lovely stay at Annette and Fred’s place - the location was great, the house was fully stocked and the hosts were extremely responsive when we had questions. Having a hot tub and gas fireplaces were an added bonus for spending the evenings admiring the views.

4.92 out of 5 average rating, 103 reviews

Home in Montara

Montara Beach Mountain Escape

SamRating, 5 stars2 weeks ago

It's a very nice place to stay, away from the city but a quick drive away. The house itself feels very roomy and the outside is beautiful with open fields and Alpacas. The stunning beaches are just minutes away! The beds aren't the best, but workable. The booking process is through a different site which feels corporate-y with every request having a price and needing to sign additional waivers and identity verifications required. The floodlight camera in the backyard is facing the sliding glass door which doesn't have any curtains and feels like I could be watched sleeping on the sofa bed in the loving room. If you can get past all that, this is a great location!

4.97 out of 5 average rating, 151 reviews

Entire house for families：Steps to beach!

EdwardRating, 5 stars2 weeks ago

Guys golf outing trip. Was our second time staying at the home. Great location near the water. Plenty of room to layout throughout. House is well kept up. Jennifer answered quickly to provide assistance when the smoke detector went off for no reason? Will stay again when in the area.

4.92 out of 5 average rating, 118 reviews

2 bedrooms house with sauna

EnderRating, 5 stars1 month ago

Peter's Airbnb was even more beautiful in person than on the listing! It has a very relaxing, cozy, and calming atmosphere with beautiful decorations. There are trails to walk around on the property that have beautiful views and beautiful plants. I had this Airbnb for a work-trip for only 3 nights, but wished I could've stayed much longer!

5 out of 5 average rating, 116 reviews

Fabulous Beach Get Away - Brand New Beach House

LaurenRating, 5 stars2 weeks ago

Had a wonderful stay at this house. The location is awesome. It was a quick walk to the beach, and great restaurants nearby. We also enjoyed the backyard which was spacious for the kids to run around and equipped with a fire pit and grill. Kitchen was massive and very modern, well equipped with supplies to cook full meals. Rita was very responsive, even helped us find a bicycle pump in the house immediately after we messaged. Would definitely stay again next time we are in half moon bay!