Vacation rentals in San Mateo

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Top-rated vacation rentals in San Mateo

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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
4.74 out of 5 average rating, 131 reviews

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.

Guest favorite
Home in San Mateo
4.92 out of 5 average rating, 101 reviews

SFO 10 Min • Queen 1BR • Fast WiFi •Walk 2 Grocery

Ten minutes to SFO, a short walk to Caltrain, and one block from everything you need day-to-day — this quiet San Mateo suite is the ideal Bay Area base for business travelers, airport transits, and Peninsula visitors. 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.

Guest favorite
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
4.88 out of 5 average rating, 221 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.

Top guest favorite
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
4.99 out of 5 average rating, 223 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

Top guest favorite
The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.
Home in San Carlos
4.96 out of 5 average rating, 303 reviews

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 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).

Top guest favorite
A spacious deck features two wooden directors' chairs positioned around a small circular table. Lush greenery lines the perimeter, creating a natural backdrop. A sunshade is partially visible, offering protection from the sunlight.
Guesthouse in San Carlos
4.99 out of 5 average rating, 134 reviews

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

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
4.84 out of 5 average rating, 107 reviews

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.

Guest favorite
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.
Place to stay in San Mateo
4.9 out of 5 average rating, 124 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.

Top guest favorite
A welcoming living area features a red sofa adorned with patterned pillows, accompanied by a brown armchair. A dark coffee table sits in front of the seating, while a small desk is positioned nearby. Light fills the space through large windows covered with white blinds.
Apartment in San Carlos
4.98 out of 5 average rating, 136 reviews

Beauty in San Carlos! 1 large bedroom apartment

Newly beautifully remodeled large corner unit with quaint views, this one bedroom apartment is in an Excellent location, walking distance to downtown San Carlos, to fine restaurants, parks, library, coffee, shopping, 30 minutes from San Francisco and San Jose and just minutes from Palo Alto Stanford and Menlo Park, Redwood City and San Mateo Assigned gated parking space, laundry room in the building: http://www.tourfactory.com/idxr1906024

Guest favorite
A private patio area features a hot tub and hanging planters with greenery. The space is surrounded by wooden decking and plants, providing a serene view of the lush landscape and trees beyond. Soft lighting adds a warm ambiance to the area.
Guest suite in San Mateo
4.93 out of 5 average rating, 102 reviews

Private Flr.-HOT TUB-SFO-SiliconVal.

A full private downstairs floor in my shared home is available to active Airbnb users. One large bedroom with a queen bed; private bathroom is in the 2nd bedroom (2 twins beds); large TV lounge and reading room. Beautiful patio just off the bedroom, hot tub, view of San Francisco Bay. We are halfway between San Francisco and Silicon Valley, and 15 minutes from SFO. I live upstairs. Separate, private entrance, safe parking.

Top guest favorite
A neat outdoor space features three tall planters filled with greenery and colorful flowers, positioned on a pathway of square stone pavers. Dark pebbles line the edges, contrasting with the lush green artificial grass beside the residence.
Guest suite in Foster City
4.99 out of 5 average rating, 117 reviews

New modern 1 bedroom unit

New modern 1 bedroom/studio unit in beautiful residential neighborhood near the water. Separate entrance that is fully furnished with top of the line appliances and high ceilings. Full size bed. Close access to highway 101, 92 and 280. Plenty of shopping nearby, Bridgepointe Shopping Center and Hillsdale Mall. Need to relax, stroll down to Gull Park to enjoy the water. Kayak and Stand-up Paddle Board available to borrow

Guest favorite
A modern studio bedroom features a spacious queen-size bed, dressed in a light blue quilt. Two large windows allow natural light to fill the room, complemented by a small working desk and chair. Neutral tones create a calming environment.
Guest suite in Belmont
4.94 out of 5 average rating, 122 reviews

New, modern quiet private studio

New modern private studio attached to the main house with a private staircase entrance. Easy free parking in front of the entrance. Located in heart of the Bay Area: 15 minutes to SFO airport, 19 minutes to Half Moon Bay, 17 minutes to Stanford. Enjoy nice views with morning coffee. Ideal for 1-2 guests. Working desk, wifi, tv, comfortable linens, small fridge, microwave and Phillips coffee machine.

Popular amenities for San Mateo vacation rentals

When is the best time to visit San Mateo?

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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.

All about San Mateo

Nestled between the hilly metropolis of San Francisco and urban San Jose, with the sweeping sands of Half Moon Bay to the west, the city of San Mateo boasts easy access to cultural hotspots, natural beauty, and a world-class food scene.

People are drawn here to admire nearly 45,000 artworks at the Cantor Arts Center at Stanford University, hike among the dramatic scenery at either end of Purisima Creek, and savor hard-to-beat ramen and crab nigiri at one of San Mateo’s established cluster of Japanese restaurants. There’s also public art to enjoy all around town, with vivid murals on numerous buildings, including the 1963 mosaic mural on South El Camino Real.

Less than half an hour west of San Mateo, Half Moon Bay boasts Surfers’ Beach for beginners and Mavericks for seasoned pros who want to take on wild waves. The same distance north, you can taqueria-hop in San Francisco’s Mission District and ride the city’s famous cable cars.

What are the top things to do in San Mateo?

Japanese Tea Garden

The Japanese Tea Garden is one of the main attractions in Central Park, San Mateo’s main community park. The garden covers over 16 acres of manicured lawns, including a pagoda tower, a koi pond, and a teahouse for a quiet afternoon among delicate cherry blossoms. This serene site was designed by the landscape architect who worked on the Tokyo Imperial Palace.

Coyote Point

Less than 20 minutes from downtown by bike or road, Coyote Point is a popular spot for activities like windsurfing and sailing. If you’re cycling, the San Francisco Bay Trail crosses the park, so you can extend your ride north all the way to San Francisco or south to Palo Alto. At the water’s edge, you’ll find a marina and a beach, backing onto an 18-hole golf course.

Filoli Historic House & Garden

A 15-minute drive from San Mateo, this Georgian Revival house and its pristine landscaped gardens span over 650 acres. Wander around the terraces for commanding views of the Santa Cruz Mountains and cross Fault Creek Bridge to step over the famous San Andreas Fault. A spring visit will be rewarded with fragrant cherry and apple blossom.

Quick stats about vacation rentals in San Mateo

  • Total vacation rentals

    Explore 510 vacation rentals in San Mateo

  • Verified guest reviews

    Over 18,390 verified reviews to help you choose

  • Family-friendly vacation rentals

    180 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Vacation rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    290 properties have a dedicated workspace

  • Wi-Fi availability

    510 of San Mateo vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, 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!

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