Holiday rentals in San Mateo

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Top-rated holiday rentals in San Mateo

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

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Guest favourite

Home in San Carlos

4.96 out of 5 average rating, 122 reviews

Serene Oasis in the Midst of Silicon Valley

Gaze out at the beautiful green canyon while having a morning coffee in bed. Head to the fully equipped kitchen to prepare breakfast and enjoy it outside on the balcony, surrounded by the sights and sounds of this stunning hilltop location. Close to 280. Centrally located in Silicon Valley for easy access to both San Jose and San Francisco. Deck/BBQ Lounge Area. Minimal. Enjoy life in the San Carlos hills. Drive about 5 minutes to lively San Carlos downtown for several restaurants and bars. Go hiking in Edgewood, Crestview, or Big Canyon. For a taste of big city life, adventure a bit further to San Francisco. Driving is the best option, I280 and 101 are easily accessible. Cal Train station down the hill - connects all the way from San Francisco to San Jose. Very spacious unit ( approximately 1200 sq.ft )

Guest favourite

Guest suite in Millbrae

4.77 out of 5 average rating, 725 reviews

Private 1 bedroom suite for quick SFO trip withA/C

1 bedroom 1 bathroom guest suite with private entrance. Good for a short SFO trip. But be aware it might not fit family vacation need! Newly remodeled kitchen, full bathroom, Wi-Fi, gas cooktop, coffee maker, toaster, microwave. Soft foam topper queen bed. Convenient for Bay Area commuter, 15 mins driving to SFO airport. Close to 101, 280 freeway. 30 mins driving to San Francisco or 50 mins to San Jose. 15 mins walk to grocery store, Starbucks and restaurants. Easy and free street parking.

Guest favourite

Guest suite in San Mateo

4.92 out of 5 average rating, 331 reviews

San Mateo Getaway Private 2 Bedroom

Bright & spacious 2 bedroom apartment with beautiful backyard in San Mateo. In-law apartment with private entrance dedicated to hosting guests. Located in quiet residential neighborhood, but close to activities for families and singles. Amenities include wet bar area with toaster oven, coffee maker, mini fridge and microwave! Laundry available upon request. Easy access to San Francisco/San Jose via 280 & 101. Close to SFO, Cal train/BART and Downtown San Mateo. Lots of street parking.

Guest favourite

Flat in San Mateo

4.94 out of 5 average rating, 212 reviews

Fabulous apartment in downtown San Mateo

Relax away from the hustle of the city in your apartment in downtown San Mateo. Located only two blocks from the San Mateo Caltrain, you can get to or from SF or SJ in 30 minutes. Our home has a separate entrance for the guest apartment on the second floor. Tuck yourself away in the California King sized bed, or explore downtown on foot. With over 100 restaurants in walking distance, you will not have a shortage of delicious dining. Eat out or enjoy a meal in the comfort of your home. Welcome!

Top guest favourite

Guest house in San Carlos

4.99 out of 5 average rating, 724 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 favourite

Guest suite in Belmont

4.94 out of 5 average rating, 142 reviews

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

Guest favourite

Bungalow in San Mateo

4.95 out of 5 average rating, 508 reviews

Entire Private Studio by SFO, AC/Heat/Free Parking

Entire cottage with private entrance. * self check-in with codes * free parking on driveway * AC & heating * 1 queen bed, 1 sofa (converts into twin bed) * fiber speed WiFi * kitchenette with sink, dishes & utensils, microwave, oven, mini fridge, keurig coffee maker, water boiler, NO STOVE * 15 min drive to SFO * 10 min walk to Caltrain * walking distances to restaurants, bars & groceries * located at end of cul de sac in a safe & quiet neighborhood * TV with Chromecast

Superhost

Home in San Mateo

4.89 out of 5 average rating, 192 reviews

12-Min From SFO, Tastefully Designed, Work Station

Welcome to the Laurel Pad, a home away from home. You'll enjoy the convenience this house offers - fully stocked kitchen, minutes away from amazing restaurants, supermarkets, parks, 13-min to SFO, 25-min to downtown San Francisco, and easy access to major companies around Silicon Valley. This bright and sunny house is tastefully designed and updated to offer functionality and aesthetics. You'll have access to fast wifi and dedicated driveway parking for up to two cars.

Guest favourite

Guest house in San Mateo

4.99 out of 5 average rating, 164 reviews

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

Guest favourite

Guest suite in San Mateo

4.93 out of 5 average rating, 247 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.

Top guest favourite

Guest suite in Hayward

5 out of 5 average rating, 212 reviews

★UNIQUE STAY in the middle of the BAY★ Wifi+MORE!

Newly renovated in-law SUITE B, located in the “Heart of the Bay”. Just a 5 minute drive to downtown Hayward & BART, 20 minutes from Oakland International Airport & 30 minutes from SFO. In-N- Out, SPROUTS, Raising Canes & Starbucks NOW OPEN just 4 min away!! Our guest suite is perfect for couples or professionals coming to CA for an extended stay. Enjoy the Bay Area's beauty and excitement from your stay in the middle of it all!

Top guest favourite

Guest house in San Mateo

4.93 out of 5 average rating, 225 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. *