
Holiday rentals in San Mateo
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Top-rated holiday rentals in San Mateo
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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.

Cozy, quiet family home with a view! 15 min to SFO
A wonderful place for a weekend getaway, week vacation or longer work trip. Kick back and relax in this calm, stylish space. You’ll feel right at home in this quiet neighborhood and a welcoming house. By car, conveniently located 15 minutes away from SFO airport, 5 minutes from multiple grocery stores, a shopping mall, many parks and public transit. The nearest bus stop is a 3 minute walk, and the bus can take you the Caltrain, BART or straight to your destination! We hope you enjoy your stay!

Super Private Hidden Redwood City House and Garden
Enjoy your privacy at this well appointed hidden house located in a lush jungle like garden! This house was recently redesigned with Spanish tiles, vaulted ceilings and wood beams with ornate carvings. Located under a large Redwood trees and surrounded by greenery, this is a gem for anyone seeking privacy, since it is not visible from the street, and you must enter via a large wooden gate and walk down a driveway (a "Flag lot"). Walking distance to both San Carlos and Redwood City downtowns.

Private 1 bedroom suite for quick SFO trip withA/C
1 bedroom 1 bathroom guest suite with private entrance. Good for a short SFO trip. But be aware it might not fit family vacation need! Newly remodeled kitchen, full bathroom, Wi-Fi, gas cooktop, coffee maker, toaster, microwave. Soft foam topper queen bed. Convenient for Bay Area commuter, 15 mins driving to SFO airport. Close to 101, 280 freeway. 30 mins driving to San Francisco or 50 mins to San Jose. 15 mins walk to grocery store, Starbucks and restaurants. Easy and free street parking.

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.

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.

Business-Friendly 2/1. Walk to Caltrain/Downtown.
Newly renovated, nicely decorated 2BR/1BA house (front unit of duplex) in a safe, quiet neighborhood. Cute, enclosed front yard with seating areas, trees, and water fountain. 600mbit high-speed Wifi. Master bedroom includes work desk, monitor to extend laptop, printer, and safe. Large, well-stocked kitchen. Microwave, toaster oven, filtered water. Living room has sofa, chair, 50" 4K Smart TV. Designated parking space. Minimum stay 31 days, except when fewer consecutive days are available.

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.

Modern room & loft, private entrance
Modern room & loft with private entrance & private bathroom. Completely private space + free parking + self check-in + superfast Wi-Fi (up to 940 Mbps). Conveniently located in a quiet & safe residential neighborhood with Bayhill Shopping Center, Tanforan Mall, BART and Caltrain stations nearby. Easy access to highway 101 & 280, SFO airport (6-minute drive or 3 miles), San Francisco (16-25 minute drive to downtown), and San Francisco Baking Institute (11-minute drive).

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.

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

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. *
Popular amenities for San Mateo holiday rentals
Other great holiday rentals in San Mateo

Cozy Private BR in Apartment Close to SFO

Shoreview Private Room +Private Entrance +Parking

A nice bedroom downtown

Private bedroom in shared townhome. Prime location

Living in a park

Room 4 with a private bathroom for one person only

Comfy Queen Downtown San Mateo

Room 3, Quiet Room with free parking
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $180 SGD | $173 SGD | $174 SGD | $173 SGD | $189 SGD | $191 SGD | $184 SGD | $179 SGD | $180 SGD | $171 SGD | $166 SGD | $170 SGD |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°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 18,550 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 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
520 of San Mateo holiday rentals include wifi 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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