Holiday rentals in San Mateo

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Top-rated holiday rentals in San Mateo

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Top guest favourite
A charming cottage entrance is framed by natural wood shingles and surrounded by lush greenery. A small porch is adorned with a wicker chair and colorful cushion, inviting guests to enjoy the serene outdoor space. Sunlight filters through the trees, illuminating the pathway.
Guest house in Redwood City
4.93 out of 5 average rating, 351 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Guest favourite
A bright living area features a round table with a floral centerpiece and two cushioned chairs. The backdrop displays an open kitchen with cabinetry, leading to a warmly painted bedroom door. A small plant and modern decor enhance the welcoming atmosphere, illuminated by natural light.
Home in San Mateo
4.83 out of 5 average rating, 283 reviews

❤️ Delightful 1B/1B modern with a leisure garden

This recently upgraded unit features a master bedroom with a full bathroom and two closets, along with a spacious living area. Enjoy complete privacy with a separate fence and a sunny private garden. We provide complimentary coffee and tea, and there’s free street parking available 24/7. It’s within walking distance to the Roblox office and the San Mateo Event Center, and about 10 minutes from SFO. Please note, this is not an apartment or condo building. Self check-in o& Check out with code.

Top guest favourite
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
4.92 out of 5 average rating, 350 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.

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.
Guest house in San Carlos
4.99 out of 5 average rating, 784 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.

Top guest favourite
A spacious living area features a light grey couch adorned with patterned cushions, situated in front of a glass-topped table. A small succulent plant and coasters are placed on the table, with glimpses of a neat kitchen and a dedicated sleeping area visible in the background.
Guest house in Belmont
4.92 out of 5 average rating, 111 reviews

A private and quaint gateway on Belmont Hills

Welcome to our cozy Belmont studio! This charming retreat offers a comfortable stay with its stylish design, fully equipped kitchen, and a comfortable bed. Conveniently located in Belmont, CA, you'll be close to vibrant San Mateo downtown, the scenic coastline of Half Moon Bay, and the airport. This quaint studio is tucked away on a small hill, surrounded by greenery. As a delightful bonus, you'll find a lovely lemon tree in the driveway, providing complimentary lemons for your stay.

Superhost
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, 209 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 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.
Guest house in Hillsdale
4.99 out of 5 average rating, 206 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 favourite
Home in Foster City
4.93 out of 5 average rating, 295 reviews

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.

Guest favourite
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
4.91 out of 5 average rating, 116 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 favourite
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, 111 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

Top guest favourite
A vibrant yellow dining table set for eight is positioned in a spacious open-plan area, surrounded by natural light from large glass doors. A soft, textured light fixture hangs overhead, complementing the modern aesthetic. The backdrop features a landscaped outdoor space visible through the glass.
Home in San Mateo
4.95 out of 5 average rating, 139 reviews

Super Bowl Wknd Sleeps 6 Easy Drive to Santa Clara

Visiting for Super Bowl weekend? Welcome to your calm Bay Area retreat - a cozy space for relaxed days & fireside evenings. Enjoy comfort, privacy & easy indoor-outdoor flow: Sleeps 6 | 3 bedrooms | 3 beds | 2 baths Wood-burning fireplace & fenced backyard w/ fire pit Enclosed atrium w/ custom mural Kitchen, dining area & dedicated workspace Free parking, Wi-Fi & laundry Single level home w/ private entrance

Top guest favourite
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
4.95 out of 5 average rating, 117 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 holiday rentals

When is the best time to visit San Mateo?

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Avg. price£105£100£101£100£110£111£107£104£105£99£96£99
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.

Quick stats about holiday rentals in San Mateo

  • Total holiday rentals

    Explore 540 holiday rentals in San Mateo

  • Verified guest reviews

    Over 19,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    200 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Holiday rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    290 properties have a dedicated workspace

  • Wifi availability

    530 of San Mateo holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym and BBQ grill 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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