Vacation rentals in San Mateo

4.92 out of 5 average rating, 332 reviews

A cozy living area showcases a gray sectional sofa and two accent chairs. A light-colored coffee table is centered on a patterned rug. A television sits on a console, with large sliding glass doors providing natural light and views of the backyard garden.

Guest suite in San Mateo

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.

4.99 out of 5 average rating, 734 reviews

The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.

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.

4.74 out of 5 average rating, 114 reviews

A cozy living area features a chaise lounge and a comfortable armchair, positioned near a vintage-style fireplace. A small desk is set against the wall, illuminated by a nearby lamp. Natural light brightens the space, highlighting the soft area rug and the neutral color palette.

Apartment in San Mateo

Gracious Flat in Downtown San Mateo

Don't miss your chance to stay in this historic mansion in downtown San Mateo- with new elegant touches placed throughout the flat, you can enjoy the old with the new. 3 blocks from San Mateo Caltrain, Philz coffee and all that lovely downtown San Mateo has to offer. Includes free parking & shared on site coin-operated laundry facilities. If you're modern urban people who accept noise from the train/other tenants & love the vibrant downtown diversity, this is the perfect place for you.

4.94 out of 5 average rating, 145 reviews

A spacious sleeping area features a queen-sized bed with a neutral-toned blanket, accompanied by bedside lights. A desk with a chair is positioned near a window, allowing natural light to brighten the room. A lounge chair and wall-mounted TV are visible in the corner.

Guest suite in Belmont

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. 🌲

4.92 out of 5 average rating, 366 reviews

A large window showcases a view of lush trees and a serene outdoor area. Natural light floods the space, enhancing the warm tones of the elegant decor, which includes a small decorative bicycle and a floral arrangement on a nearby table.

Home in Belmont

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

A dining area features a light wood table surrounded by four upholstered chairs. A decorative bench sits along one side of the table. Two abstract art pieces adorn the wall, and a potted plant adds a touch of greenery in the corner. Natural light enters through a large window.

4.89 out of 5 average rating, 197 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.

4.99 out of 5 average rating, 166 reviews

A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.

Guesthouse in Hillsdale

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

A living area is highlighted by a light-toned laminate floor and neutral-colored walls. Two soft armchairs with yellow cushions face a modern white sofa. A round coffee table is placed atop a patterned area rug. A tall plant stand holds greenery, complementing the inviting space.

4.89 out of 5 average rating, 350 reviews

Cozy San Mateo home / Near SFO Airport

Looking for the perfect short-term rental in the Bay Area? This fully furnished 3-bed, 2-bath home in San Mateo is ideal for families, business travelers, and vacationers. Located just six blocks from vibrant downtown, you’ll be steps from ethnic restaurants, boutique shopping, and local charm. Just 10 minutes from SFO airport. Easy access to San Francisco and San Jose. This inviting home is your ideal base for experiencing the best of the Peninsula.

4.93 out of 5 average rating, 249 reviews

A bright bedroom features a spacious bed with crisp white linens and an accent pillow. Natural light streams through large windows, and a modern desk with a lamp is positioned nearby. A mirrored closet reflects the room's stylish decor, enhancing the space's openness.

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.

4.93 out of 5 average rating, 227 reviews

The entrance to the studio features double glass doors framed by potted plants and flowers in various sizes. A welcome mat is positioned at the threshold, and small wall-mounted lights provide illumination. Natural light can be seen streaming through the doors.

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. *

4.97 out of 5 average rating, 444 reviews

A private deck area is surrounded by lush greenery and colorful shrubs. A large umbrella provides shade over the wooden table and chairs, inviting relaxation outdoors. The deck is accessible from the yard, enhancing the tranquil outdoor experience.

Apartment in Burlingame

Home away from home in wonderful Burlingame

It's my honor to be your host and I will try to make your stay really great. I provide suggestions of things to do but feel free to ask for advice! Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price has been increased to reflect that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

Guesthouse in Hillsborough

The cottage entrance is shown, featuring a green door framed by a screen door. A small outdoor seating area with two chairs and a table is visible on a gravel path, surrounded by lush greenery and trees.

4.95 out of 5 average rating, 924 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.

Vacation rentals for every style

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Popular amenities for San Mateo vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in San Mateo

Guesthouse in San Mateo Park

The exterior of the cottage is shown, featuring a dark front door framed by two large windows. Potted plants with colorful blossoms sit on either side of the entrance, adding a touch of greenery to the facade, which is painted in a soft gray tone.

5 out of 5 average rating, 15 reviews

Stowe Cottage in San Mateo Park, California

4.94 out of 5 average rating, 33 reviews

A modern kitchen is shown with light-colored cabinetry and stainless steel appliances. A wooden dining table with two chairs is positioned nearby. Soft lighting creates a functional space, and a window offers natural light, complemented by warm-toned walls.

Guesthouse in San Mateo

Sparklingly clean guest unit with gated parking

4.94 out of 5 average rating, 153 reviews

A modern guest suite is highlighted by a queen bed with crisp white linens against a neutral wall. Two large windows provide natural light, accompanied by elegant curtains. A stylish chair and small table create a cozy seating area, while a mirror and plants add to the inviting decor.

Guest suite in San Bruno

Stylish Private Guest Suite Near SF and SFO

4.76 out of 5 average rating, 41 reviews

A well-arranged bedroom features a spacious bed adorned with sunflower-themed pillows. A colorful area rug brightens the floor, and sunlight filters through the window adorned with dark curtains. A shelf with decorative items and a pathway leading to a private bathroom can also be seen.

Guesthouse in Hillsdale

Private Room Close to Caltrain & Hillsdale Mall

A dedicated workspace is showcased with a wooden desk, a comfortable chair, and a modern monitor. Natural light filters through blinds, illuminating the area. A small globe and a notebook sit on the desk, while a cozy stone fireplace adds warmth to the setting.

5 out of 5 average rating, 3 reviews

Executive Home w/ Sun Deck

A modern kitchen area features sleek white cabinetry and a geometric tile backsplash. An electric cooktop and a kitchen sink with a modern faucet are visible, alongside essential appliances including a microwave and coffee maker. Natural light enters from a nearby doorway leading to the bedroom.

4.88 out of 5 average rating, 66 reviews

Modern & Private 1BR w/ AC | Walk 2 Grocery, Shops

An open-plan living area showcases a modern design with a large wall-mounted television above a fireplace. Comfortable seating arrangements include a cozy orange armchair and a plush white sofa. A dining table with stylish chairs is visible in the background, complemented by decorative shelves.

4.74 out of 5 average rating, 19 reviews

San Mateo Happy Haven Home w Patio/Projector