Vacation rentals in San Mateo County

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Top-rated vacation rentals in San Mateo County

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Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 585 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.

Jun 19 – 26

G$32,063 GYD per night

Guest favorite

Guest suite in Boulder Creek

4.98 out of 5 average rating, 425 reviews

Enjoy Private Redwoods from Your Bed or the Deck

Come and visit our own private slice of the REDWOOD FOREST with over 40 trees and large deck to enjoy them. Wake up to fresh mountain air, a view of nature and coffee. After a day of WINE tasting, HIKING, BEACHES, or exploration, bring a bottle back and sprawl in comfort reflecting, chatting, or sipping on the deck. The perfect little getaway spot. Treat yourself to some nature with us. A winter fireplace, easy walking and parking makes this scene. 1.5 miles to downtown Boulder Creek and fun!

Aug 15 – 22

G$28,881 GYD per night

Guest favorite

Guest suite in Woodside

4.88 out of 5 average rating, 339 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

Sep 29 – Oct 6

G$28,792 GYD per night

Guest favorite

Guest suite in Redwood City

4.94 out of 5 average rating, 294 reviews

Beautiful Studio

Studio with a private entrance, your own private kitchen, dining area and all cooking utensils, fully equipped. TV 50” with roku, netflix, amazon prime through WiFi. The studio has its own separate heating unit and AC. Bath robes and feather down-quality linen. Well insulated, wheelchair ok Code operated, lock door Minutes away from Stanford. We use eco-friendly cleaning products. Easy parking always available. Comfortable queen bed. Portable cot and bedding available upon request.

Feb 4 – 11

G$25,600 GYD per night

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 145 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

Oct 4 – 11

G$22,428 GYD per night

Guest favorite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 146 reviews

Elegant retreat in Redwood City

Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. All furnishings are selected by a professional decorator and routinely upgraded. This is part of a ~4000 sq ft luxury single family home with 2 completely separate and private entrances.

Mar 21 – 28

G$25,793 GYD per night

Guest favorite

Guest suite in El Granada

4.97 out of 5 average rating, 213 reviews

Cozy, creekside guest suite with private entrance

Cozy, creekside guest suite just blocks from the beach and the picturesque harbor. This one bedroom unit has been completely remodeled with a fully stocked kitchen, a separate eating/work space and a bathroom with a walk in shower. Drink your morning coffee (host provided) on the furnished deck while listening to the sounds of the running creek and the fog horn in the distance. This unit has its own private entrance and is closed off from the rest of the house.

Sep 16 – 23

G$30,534 GYD per night

Guest favorite

Home in Montara

4.97 out of 5 average rating, 273 reviews

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

May 3 – 10

G$29,746 GYD per night

Guest favorite

Guest suite in San Mateo

4.94 out of 5 average rating, 205 reviews

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.

May 27 – Jun 3

G$31,254 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 380 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.

Jan 15 – 22

G$24,296 GYD per night

Superhost

Guesthouse in San Mateo

4.84 out of 5 average rating, 160 reviews

Charming cozy studio King-sized bed

Hi there! Welcome to our cozy studio in the heart of the bay area. You'll find yourself conveniently located to downtown San Mateo and all the transportation. This is a shared walkway, private studio. The unit has 1 king sized bed with ample pillows. Included are fast wifi, 43" TV, Netflix, coffee, full kitchenette for light cooking. Self-check in. No central heat, no AC unit. Equipped with space heater

Mar 16 – 23

G$29,391 GYD per night

Guest favorite

Guesthouse in San Mateo

4.93 out of 5 average rating, 193 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. *

Oct 7 – 14

G$28,455 GYD per night