Holiday rentals in San Mateo
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Top-rated holiday rentals in San Mateo
Guests agree: these stays are highly rated for location, cleanliness and more.
Eichler home w/ atrium, BBQ & fire pit
Step into a beautifully preserved 1956 Eichler home in San Mateo - where mid-century architecture, an enclosed atrium w/ custom mural, and a private backyard come together for an Bay Area stay. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ BBQ, fire pit & 8-person outdoor dining - Wood-burning fireplace & sun-filled open-concept living - Private office w/ dedicated workspace - great for remote work - Full kitchen, laundry & TV - 20 mins to SF | 15 mins to SFO | near Caltrain
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High Ceilings! Modern Spacious Bright 4BR Home
A Hidden Gem! Spacious, tastefully designed, newly renovated modern home on a charming cul-de-sac in Foster City. Ideal open layout with 16ft vaulted ceilings, abundant natural light, expansive backyard with grill and full amenities, making for a great space to entertain and unwind in comfort & style. Centrally located between San Francisco & Silicon Valley. Close to SFO airport, caltrain, restaurants, markets, San Mateo, Stanford, Palo Alto. Perfect for business travelers or family vacations.
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Private Cottage near Redwood City and San Carlos Downtowns
Quiet, private two-level garden cottage ideal for business travelers and visiting family. Gig+ high-speed Wi-Fi, workspace, central AC & heat, king-size bed, private entry (24/7), 50” 4K TV, fully equipped kitchen with granite countertops, and guest-exclusive washer and dryer. Bedroom, living area, kitchen, bathroom, and dining / work space. Shared garden with BBQ, teak table and hot tub. Walkable to transit, downtown areas, and a popular breakfast café. Some train and light traffic noise.
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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.
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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.
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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
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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).
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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.
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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.
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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!
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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.
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❤️ Delightful 1B/1B modern with a leisure garden
This beautifully upgraded private garden home features a spacious primary bedroom with a full bathroom and two closets, plus a bright and inviting living area. Enjoy added privacy with a separate entrance and a sunny garden setting. Complimentary coffee and tea are provided, and free street parking is available 24/7. Walking distance to the Roblox office, the San Mateo Event Center, and the scenic lakeside trail. About 10 minutes from SFO.
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Popular amenities for San Mateo holiday rentals
Other great holiday rentals in San Mateo
Business-Friendly 2/1. Walk to Caltrain/Downtown.
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Private Room Close to Caltrain & Hillsdale Mall
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Adorable 1 bedroom guest house w/ AC in San Carlos
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Newly renovated 2bed/1bath home
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Private Modern Studio & Patio with stunning views
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San Mateo Prime Location 1 Bedroom Suite
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Luxury guesthouse close to SFO/Parking/waterfront
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Private Ensuite with Kitchenette & Beautiful Yard
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When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $185 SGD | $187 SGD | $190 SGD | $171 SGD | $187 SGD | $189 SGD | $182 SGD | $177 SGD | $178 SGD | $181 SGD | $185 SGD | $183 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 510 holiday rentals in San Mateo
Verified guest reviews
Over 18,390 verified reviews to help you choose
Family-friendly holiday rentals
180 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 120 rentals that welcome pets
Holiday rentals with a pool
100 properties feature pools
Rentals with dedicated workspaces
290 properties have a dedicated workspace
Wifi availability
510 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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