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Vacation rentals in San Mateo County

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Top-rated vacation rentals in San Mateo County

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

Guest favorite
Guesthouse in Woodside
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.
Mar 10 – 17
$294 per night
Guest favorite
Home in Moss Beach
Walk to the Beach from this Ocean Front Home
Your beachfront escape awaits you. Come immerse yourself in the serenity of this Pacific Ocean retreat gracefully set in a secluded beach just 25 mins south of San Francisco. This 2 bed / 2 bath home features breathtaking ocean views and direct beach access just a few steps down. The hot tub overlooking the ocean, fire pits and a putting green complete this idyllic space. Comfortably sleeps 4 adults on 2 king beds and 2 high quality airbeds are provided for total sleeping for 6.
Apr 2 – 9
$892 per night
Guest favorite
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.
Jul 23 – 30
$167 per night

Popular amenities for San Mateo County vacation rentals

Other great vacation rentals in San Mateo County

Guest favorite
Guest suite in Emerald Hills
Elegant retreat in Redwood City
Nov 22 – 29
$106 per night
Guest favorite
Camper/RV in Half Moon Bay
Airstream Coastal Hideaway (Sunset)
Aug 23 – 30
$269 per night
Guest favorite
Guest suite in El Granada
Cozy, creekside guest suite with private entrance
Mar 8 – 15
$128 per night
Superhost
Apartment in Pacifica
Luxury Beach View Apartment
Jan 9 – 16
$149 per night
Guest favorite
Guest suite in San Mateo
San Mateo Getaway Private 2 Bedroom
May 9 – 16
$137 per night
Guest favorite
Home in San Mateo
Casita By The Bay, San Mateo
May 20 – 27
$148 per night
Guest favorite
Guesthouse in Boulder Creek
Custom Tiny Home Retreat in the Redwoods
Apr 19 – 26
$115 per night
Guest favorite
Guesthouse in Burlingame
Paloma Cottage under a tree
Aug 3 – 10
$112 per night
Guest favorite
Guest suite in Boulder Creek
Enjoy Private Redwoods from Your Bed or the Deck
Jul 6 – 13
$112 per night
Guest favorite
Guesthouse in Woodside
Guest House in the Woods
Jun 16 – 23
$180 per night
Guest favorite
Home in San Mateo
12-Min From SFO, Tastefully Designed, Work Station
Oct 13 – 20
$270 per night
Guest favorite
Guest suite in Boulder Creek
Redwood Riverfront Getaway
Dec 22 – 29
$94 per night

Destinations to explore