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Holiday houses in San Mateo

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Quick stats about holiday rentals in San Mateo

  • Total holiday rentals

    Explore 510 holiday rentals in San Mateo

  • Verified guest reviews

    Over 19,160 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wi-Fi availability

    510 of San Mateo holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ and Laptop-friendly workspace across San Mateo rentals

  • 4.8 Average rating

    San Mateo stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in San Mateo

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

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Top Guest favourite
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.

ValueFamilyLong stay

4.99 out of 5 average rating, 856 reviews
Guest favourite
A spacious living area features modern furnishings, with large windows offering natural light. A full-size pool table and foosball table are visible in separate areas. An outdoor basketball hoop and Tesla charging station are also present, enhancing the recreational offerings of the home.
Villa in San Mateo

Tesla EV Charger Basketball Pool Table Hot Tub Spa

Luxury Getaway at our Silicon Valley home w/3300+ SqFt of fun space. Spend less time waiting at charging station and more time enjoying your vacation! FREE Tesla /EV charger on site, hot tub spa, Basketball, pool table, & Foosball. 15 min to SFO Airport, 20 min to Stanford/San Francisco, 25 min drive to San Jose SJC. Newly furnished w/high quality touches and located in a safe neighborhood yet just 3 min from grocery and dinning. Perfect place to work & relax with easy access to 101/280 HWY.

FamilyLocationCleanliness

5.0 out of 5 average rating, 76 reviews
Superhost
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

Graceful 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.

LocationValueGetting around

4.71 out of 5 average rating, 146 reviews
Guest favourite
An inviting living room features a large sectional sofa and a light rug centered under a TV stand. Natural light illuminates the space through multiple windows, and hardwood floors enhance the clean, modern design. Decor elements include a framed artwork and indoor plants.
Home in San Mateo

SanMateo Comfortable 2BR Home/WiFI & Free Parking

Welcome to this entire newly remolded 2-bedroom home , located in a desirable neighborhood. The home offers a spacious living space with a very clean and fresh interior design. You’ll be close to downtown San Mateo’s restaurants and shops, the beautiful Japanese Garden at Central Park, Hillsdale Shopping Center, and major routes including Highway 101 and Highway 92. SFO is just a short drive away, making this a convenient home base for both business and leisure travel. SFO 5miles

FamilyValueQuiet

4.85 out of 5 average rating, 100 reviews
Guest favourite
Home in San Mateo

SFO 10 min, Stylish Suite, Walk to Grocery

Ten minutes to SFO, a short walk to Caltrain, and one block from cafés and restaurants— this private San Mateo suite is the ideal Bay Area base for business travelers, airport transits and couples exploring the peninsula. Settle into a comfortable queen bed with room-darkening shades, pull up a dedicated workspace with 789 Mbps WiFi, and unwind with Netflix, HBO Max, Disney+, Hulu, or Amazon Prime on the smart TV. Everything is taken care of so you can focus on why you're here.

LocationValueNearby

4.93 out of 5 average rating, 126 reviews
Guest favourite
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 San Mateo

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

ValueLocationLong stay

4.98 out of 5 average rating, 254 reviews
Guest favourite
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.
Home in San Mateo

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.

ValueFamilyBathroom

4.88 out of 5 average rating, 247 reviews
Superhost
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.
Home in San Mateo

Relaxing Backyard Retreat -Spacious + Bright Home

Escape, relax, and recharge at our beautiful 3-bedroom, 2-bath retreat in San Mateo, perfectly designed for families, friends, and remote workers seeking comfort and convenience. Featuring a modern open-concept layout, this spacious home is ideal for gathering, entertaining, or unwinding in style. Step outside to your private backyard oasis with lush greenery, a cozy patio, and glowing string lights,the perfect spot to enjoy peaceful Bay Area evenings.

FamilyLocationCheck-in

4.83 out of 5 average rating, 122 reviews
Top Guest favourite
A spacious living room features large windows allowing for ample natural light. Comfortable seating is arranged with a gray sofa and dark armchairs. A glass coffee table sits atop a plush area rug, while artwork adorns the walls, adding a touch of color to the neutral palette.
Home in San Mateo

Serene Modern Home with Yard & Parking

This spacious, tastefully decorated and full of natural light large house is a perfect combination of comfort and style. The house is recently renovated and has got everything to accommodate all your needs for a perfect stay. Convenient strategic location and easy commute to SF, Silicon Valley, BART and Airport, full amenities, parking, safe and quiet neighborhood, professionally managed, immaculately clean and more. Book now before someone else does!

LocationFamilyParking

4.92 out of 5 average rating, 319 reviews
Top Guest favourite
Home in Foster City

Lagoonfront Retreat: 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.

ValueLocationView

4.93 out of 5 average rating, 326 reviews
Superhost
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.

FamilyValueLaundry

4.91 out of 5 average rating, 278 reviews
Top Guest favourite
Home in San Mateo

Panoramic Bay View • Single-Level • 1Gbps WiFi

Wake up to breathtaking Bay views in a serene, private single-level retreat with 2,150 sq ft of thoughtfully designed living space. Ideal for families or small groups, with easy access to San Francisco, Silicon Valley, and Bay Area events. Surrounded by flowers, fruit trees, and beautiful Bay views, this peaceful retreat invites you to slow down and enjoy life’s simple moments.

LocationFamilyParking

5.0 out of 5 average rating, 27 reviews

Popular amenities for San Mateo holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near San Mateo's top sights

Hillsdale Shopping Center

171 locals recommend

Coyote Point County Recreational Area

72 locals recommend

CuriOdyssey

48 locals recommend

San Mateo Central Park

38 locals recommend

Japanese Tea Garden

36 locals recommend

Washington Park

35 locals recommend

Other great holiday rentals in San Mateo

Top Guest favourite
The living room features two cozy sofas arranged for relaxation, with a coffee table positioned in the center. A smart TV is mounted on the wall, while a glass door opens to a balcony. Natural light fills the space, enhancing the modern decor.
Apartment in San Mateo

1725 - Modern & Cozy 2B2B at Heart of San Mateo

ValueFamilyAmenities

4.94 out of 5 average rating, 53 reviews
Superhost
A spacious living area features large windows allowing natural light to fill the space. A cozy sectional sofa is complemented by a contemporary coffee table. A dining area with seating for six is visible, accompanied by a modern lighting fixture above.
Home in San Mateo

SanMateo Cozy Central 3B1b home/Garage parking AC

ValueLocationParks

4.76 out of 5 average rating, 91 reviews
Guest favourite
A cozy seating area is displayed with a plush chair in a deep hue, positioned next to a contemporary entertainment unit. A flat-screen television is mounted on the wall, and decorative elements, including a small potted plant and a vase, add a touch of greenery.
Apartment in San Mateo

Cozy in Heart of San Mateo Restaurant Scene w/AC

FamilyLocationQuiet

4.95 out of 5 average rating, 73 reviews
Top Guest favourite
A modern kitchen is presented, featuring a spacious island with seating for four. Sleek stainless steel appliances are complemented by white cabinetry and a stone backsplash. Natural light floods through a skylight, enhancing the vibrant blue accent wall and warm wood flooring.
Home in Foster City

Lavish Modern Home 4BR near SFO/Palo Alto/Stanford

FamilyLocationKitchen

5.0 out of 5 average rating, 85 reviews
Top Guest favourite
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 San Mateo

Spacious, Remodeled 2BR Duplex Unit by Downtown SM

ValueLocationParking

5.0 out of 5 average rating, 75 reviews
Top Guest favourite
A cozy living area features two brown leather chairs with decorative pillows, positioned in front of a fireplace. A Christmas tree stands nearby, and a hammock is visible through the sliding glass door, leading to a private backyard with greenery.
Home in San Mateo

Spacious house downtown San Mateo

ValueLocationKitchen

5.0 out of 5 average rating, 41 reviews
Top Guest favourite
Home in San Mateo

3BR/3BA House 8 min from SFO | Free Parking

FamilyLocationSleep quality

4.95 out of 5 average rating, 21 reviews
Superhost
Home in Woodside

Redwood Forest A-Frame Retreat in the Bay Area

LocationSleep qualityIndoor spaces

5.0 out of 5 average rating, 8 reviews

When is the best time to visit San Mateo?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$206 AUD$209 AUD$212 AUD$206 AUD$215 AUD$242 AUD$203 AUD$198 AUD$199 AUD$202 AUD$206 AUD$205 AUD
Avg. temp11°C12°C13°C14°C16°C17°C18°C18°C19°C17°C14°C11°C

Frequently Asked Questions

  • What are the best places to stay in San Mateo?

    San Mateo has inviting neighborhoods like Bay Meadows and Downtown, known for walkable streets and access to dining and shopping. The Hillsdale area features leafy, quiet surroundings, making it popular for families and groups.

  • What are the best things to do in San Mateo with kids?

    Families can explore Coyote Point Recreation Area, which has large playgrounds, picnic spots, and a science-focused museum. Central Park is often recommended for its miniature train rides, gardens, and open space to enjoy together.

  • What are some of the best things to do in San Mateo?

    Stroll through the Japanese Garden in Central Park, explore the interactive exhibits at CuriOdyssey, or enjoy outdoor activities along the Bay Trail. San Mateo’s dining scene around Downtown is often suggested for tasting regional and international flavors.

  • How is the weather in San Mateo?

    San Mateo has mild conditions year-round, with winters near 45–58°F (7–15°C) and summers around 55–73°F (13–23°C). Rain is most frequent from November through March, while summer months are typically dry.

  • When is the best time to visit San Mateo?

    Late spring through early fall is often recommended for its dry, mild days and minimal rainfall. Seasonal events and outdoor activities are popular during these months, with comfortable temperatures for city exploring.

  • What are the best places to visit in San Mateo?

    Coyote Point Recreation Area is frequently suggested for waterfront views and nature activities, while the Japanese Garden in Central Park draws visitors with its peaceful landscaping. The Downtown area has vibrant shops and cultural venues.

  • What are some hiking trails in San Mateo?

    San Mateo has the Sawyer Camp Trail, often recommended for walking, running, and cycling, where you can take in views of Crystal Springs Reservoir and shaded groves. Trails at Coyote Point Recreation Area feature opportunities for wildlife observation and access to outdoor picnic spaces.

  • What are some family activities we can do in San Mateo?

    Families often explore outdoor fun at Central Park or Coyote Point Recreation Area, and visit hands-on exhibits at CuriOdyssey. The Hillsdale Shopping Center is another spot with play zones and dining options suited for all ages.

  • What are some of the best day trip ideas from San Mateo?

    The San Francisco Bay Area surrounds San Mateo with distinct day-trip options, including visiting museums, urban parks, and scenic coastlines near Pacifica or Half Moon Bay. Wine tasting and art tours in nearby communities are frequently suggested for visitors.

  • Are there any pet friendly accommodations available in San Mateo?

    Many accommodations in San Mateo welcome pets, especially those around Downtown, Hillsdale, and Bay Meadows neighborhoods. Parks like Central Park feature pet-friendly paths for walks and outdoor relaxation.

  • What are some local tips for visiting San Mateo?

    Locals recommend layering clothing for shifting temperatures and exploring farmer’s markets to experience fresh regional produce. Early mornings are quieter at parks, and many galleries or cafes showcase local artists throughout the year.

  • What is San Mateo known for?

    San Mateo is known for its leafy parks, Japanese-inspired gardens, and strong focus on community events. Its dining scene embraces international flavors, and nearby waterfront areas attract those interested in nature or recreation.

  • What are the best hidden gems to explore in San Mateo?

    The Japanese Garden in Central Park is a serene spot that many visitors overlook. Locally owned bookshops and independent galleries around Downtown are also frequently suggested by residents for unique finds and art displays.

  • What are the best foods to try in San Mateo?

    San Mateo’s dining scene has diverse flavors such as ramen, sushi, Filipino specialties, and fusion dishes. Bakeries and markets showcase local produce in pastries and fresh salads, while cafés serve specialty coffee blends.

  • What should I bring for a trip to San Mateo?

    Pack layered clothing to adjust to cool mornings and warm afternoons, as well as comfortable walking shoes. A reusable water bottle and rain jacket are practical for exploring outdoors, especially if visiting in the wetter months.

  • What is the nightlife in San Mateo like?

    Nightlife in San Mateo centers around Downtown, featuring friendly pubs, cocktail lounges, and restaurants with live music on select evenings. Some venues host trivia nights or open mic events, drawing a relaxed local crowd.

  • What are the most popular events or festivals in San Mateo?

    San Mateo hosts community events like summer music series in Central Park, cultural fairs, and the San Mateo County Fair, which is often recommended for its family-friendly activities. Farmers’ markets and local art walks are year-round gatherings.

  • Are there family friendly vacation rentals in San Mateo?

    San Mateo has many family-friendly vacation rentals in neighborhoods like Hillsdale, Bay Meadows, and areas near Central Park. These locations are close to playgrounds, open spaces, and local eateries frequented by families.

Destinations to explore