Holiday houses in San Mateo

4.96 out of 5 average rating, 191 reviews

The sunroom features expansive glass windows that offer a panoramic view of the city and hills at sunset. A cozy seating area with a light blanket and soft cushions is present, providing a relaxing space to enjoy the scenic landscape.

Home in Daly City

SF Amazing View & SUNroom: Spacious Private 1 bdrm

👋 Welcome to our spacious, clean, private getaway studio on Southern Hill in Daly City. Escape the hustle and bustle of the city. Enjoy a stunning view of day/night in clear days ☀️ - Easy street parking - Great Summit Loop Trail at San Bruno Mountain (6-min🚘) - Cow Palace Arena (8-min🚘) - H Mart grocery mall (10-min🚘) - 9.2 miles to SFO (17-min🚘) - 6.7 miles to Civic Center（>30-min🚘 w/ traffic or 20-min🚘 w/o traffic) - 11 miles to Fisherman's Wharf(>35-min🚘 w/ traffic or 23-min🚘 w/o traffic)

A light-filled living room features a comfortable white sofa and a stylish armchair, positioned around a wooden coffee table. A modern television is mounted above a decorative stone fireplace. Soft curtains frame the window, enhancing the open feel of the space.

4.86 out of 5 average rating, 111 reviews

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat

Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

4.99 out of 5 average rating, 771 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, 123 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.

4.95 out of 5 average rating, 155 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. 🌲

4.96 out of 5 average rating, 310 reviews

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

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.

4.93 out of 5 average rating, 376 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

4.99 out of 5 average rating, 192 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.

4.9 out of 5 average rating, 363 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, 282 reviews

Home in Foster City

Tranquil Lagoon View 3BR House Near SFO

Our stunning Airbnb listing offers both convenience and relaxation. 5min to multiple supermarkets and 15mins to SFO. Enjoy breathtaking views of the lagoon, modern decor, a fully-equipped kitchen, two comfortable living areas, and three cozy bedrooms with high-quality linens. We provide high-speed Wi-Fi, working desks, and heating for your comfort. We look forward to hosting you and helping you make the most of your stay in this beautiful area.

Place to stay in San Mateo

A scenic outdoor area is visible, featuring a trampoline alongside a grassy space. A deck extends toward the water, where a blue kayak and a boat with a cover are stationed. A shaded seating area is located nearby, with a view of the serene lake.

4.9 out of 5 average rating, 111 reviews

Cottage on the Water -SUP,Kayaking,Canoeing

Private Club House Water Front. Free use of stand-up paddle board, kayak, and canoe. Private entrance with Smartlock and wifi. Modern studio with full bathroom. and the kitchenette area is fully furnished for light cooking. Conveniently located near grocery, Target, Trader Joes, and restaurants. 5 minutes from Downtown San Mateo, and 10 minutes from SF Airport. Looking to get away from the bay area without actually leaving, nice escape.

4.92 out of 5 average rating, 255 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, and microwave. 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.

Popular amenities for San Mateo holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in San Mateo

A cozy studio space is shown featuring a spacious bed with multiple pillows. A compact kitchenette area is visible next to the bed. Natural light enters through a window with blinds, while a bathroom doorway with organized towels is at the back, enhancing functionality.

Guesthouse in San Mateo

4.82 out of 5 average rating, 192 reviews

Charming cozy studio King-sized bed

4.96 out of 5 average rating, 75 reviews

The living area features a leather sofa paired with a patterned rug and a glass coffee table. A dining area is visible in the background, illuminated by natural light from large windows. Soft decorative elements, including a fluffy pouf and indoor plants, enhance the welcoming ambiance.

Home in Belmont

Sunlit 2B1B house w/ Deck & Garden on Belmont hill

5 out of 5 average rating, 46 reviews

A modern kitchen is presented with white cabinetry and light-colored countertops. A stainless steel stove is located against a backsplash of light tiles. Two wooden bar stools are placed at a breakfast counter, with shelving displaying decorative plants and framed photos above.

Home in Hayward Park

Spacious, Remodeled 2BR Duplex Unit by Downtown SM

4.91 out of 5 average rating, 69 reviews

An outdoor breakfast bar is featured, constructed of natural wood with a polished countertop. Several decorative items are placed on the bar, while four metal chairs with intricate designs are arranged nearby. Sunlight highlights the wooden textures and accents of the surrounding greenery.

Guest suite in San Mateo

Luxury guesthouse close to SFO/Parking/waterfront

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.

4.75 out of 5 average rating, 28 reviews

San Mateo Happy Haven Home w Patio/Projector

5 out of 5 average rating, 64 reviews

An open living space features a spacious sectional sofa adorned with a decorative throw. Natural light floods through large windows and skylights, enhancing a bright atmosphere. A dining area is visible in the background, complemented by a modern kitchen equipped with stylish cabinetry.

Home in Foster City

Resort Style, Modern Home 3BR near SFO, Stanford

5 out of 5 average rating, 16 reviews

Guest suite in San Mateo

Private suite in a house

An outdoor seating area features a spacious table surrounded by ten chairs, complemented by a cozy texture of orange cushions on a wicker sofa. A fire pit occupies the center, with a sunshade above to provide comfort during warm days.