Vacation rentals in San Mateo

Guesthouse in Redwood City

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.

4.93 out of 5 average rating, 333 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.

4.95 out of 5 average rating, 128 reviews

A spacious living area features mid-century furniture, including a sofa with colorful cushions and wooden armchairs. A wood-burning fireplace is positioned within a textured white wall. Large glass doors provide natural light and an inviting view of the outdoors, enhancing the open layout.

Home in San Mateo

Modern Eichler retreat w/ patio & fire pit

Welcome to your stylish Bay Area retreat - a mid-century modern Eichler home blending timeless design w/ modern comfort. Perfect for families, remote workers & weekend getaways: • Sleeps 6 | 3 bedrooms | 3 beds | 2 baths • Private fenced backyard w/ fire pit, BBQ & dining for 8 • Enclosed atrium w/ custom mural & red maple tree • Private office w/ fast Wi-Fi & dedicated desk • Fully equipped kitchen & cozy wood-burning fireplace • Peaceful Highlands neighborhood - 15 mins to SFO, 20 mins to SF

4.77 out of 5 average rating, 745 reviews

A cozy living area features a grey sofa adorned with colorful cushions. A sleek black coffee table sits in front of a modern television, with a decorative plant nearby. Bright yellow curtains covered in floral patterns frame the window, allowing natural light to illuminate the space.

Guest suite in Millbrae

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.

4.92 out of 5 average rating, 337 reviews

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

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.

4.99 out of 5 average rating, 747 reviews

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.

4.74 out of 5 average rating, 116 reviews

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

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.

4.95 out of 5 average rating, 148 reviews

A spacious sleeping area features a queen-sized bed with a neutral-toned blanket, accompanied by bedside lights. A desk with a chair is positioned near a window, allowing natural light to brighten the room. A lounge chair and wall-mounted TV are visible in the corner.

Guest suite in Belmont

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

4.92 out of 5 average rating, 372 reviews

A large window showcases a view of lush trees and a serene outdoor area. Natural light floods the space, enhancing the warm tones of the elegant decor, which includes a small decorative bicycle and a floral arrangement on a nearby table.

Home in Belmont

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

4.99 out of 5 average rating, 173 reviews

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

4.93 out of 5 average rating, 249 reviews

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, microwave and a Keurig coffee maker. 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.

Place to stay in San Mateo

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.

4.91 out of 5 average rating, 105 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.

4.94 out of 5 average rating, 104 reviews

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

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for San Mateo vacation rentals

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

San Mateo apartment rentals

4.99 out of 5 average rating, 278 reviews

A framed view from the unit showcases a scenic landscape of greenery and distant urban areas. The balcony railing provides an open perspective of the surrounding trees and hills, with a glimpse of the sky dotted with soft clouds.

Apartment in Oakland

Modern retreat in the tree tops

4.87 out of 5 average rating, 168 reviews

A compact kitchen area is equipped with modern appliances, including a refrigerator and stove. A wooden table with two chairs is set in front, with bowls of fruit and a globe nearby. Open shelving displays books and decorative items, creating a functional space.

Apartment in Berkeley

Grandmas bi-coastal retreat

4.97 out of 5 average rating, 219 reviews

A modern green sectional sofa features colorful throw pillows with geometric patterns. Above the sofa, a gallery wall displays a collection of framed art pieces. A skylight allows natural light to brighten the space, enhancing the relaxed atmosphere.

Apartment in Oakland

El Nido—a Magnificent Victorian Home

Apartment in Redwood City

A welcoming studio space is captured from the entrance, featuring a spacious lounge area with a white sofa and a patterned chair. Natural light flows through large windows, illuminating the open kitchenette and a queen size bed in the background.

4.97 out of 5 average rating, 117 reviews

Luxury Studio in the heart of Silicon Valley

4.88 out of 5 average rating, 100 reviews

A bright and airy bedroom features a spacious bed with white bedding and a blue accent blanket. Natural light filters through two windows, illuminating the room. A wooden nightstand with a lamp is positioned next to the bed, and art pieces adorn the walls.

Apartment in Palo Alto

Studio Apartment with Kitchenette Alcove

4.97 out of 5 average rating, 147 reviews

A panoramic view captures the sun setting over the ocean, with a gradient of colors blending into the sky. Gentle waves reflect the warm tones of the sunset, while green coastal vegetation lines the foreground, offering a serene backdrop to the seascape.

Apartment in Pacifica

Newly Updated Guest Suite w/ Sweeping Ocean Views

4.98 out of 5 average rating, 127 reviews

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

Beauty in San Carlos! 1 large bedroom apartment

Apartment in Mountain View

A modern living space features a colorful geometric accent wall and a large screen displaying 'NETFLIX'. Comfortable seating arrangements are complemented by plants and decorative items. Natural light fills the room through multiple windows, while a small table adds to the inviting atmosphere.

4.9 out of 5 average rating, 120 reviews

New Beautiful & Lovely Home | Dtown Mountain View

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Other great vacation rentals in San Mateo

4.9 out of 5 average rating, 354 reviews

A living area is highlighted by a light-toned laminate floor and neutral-colored walls. Two soft armchairs with yellow cushions face a modern white sofa. A round coffee table is placed atop a patterned area rug. A tall plant stand holds greenery, complementing the inviting space.

Home in San Mateo

Cozy San Mateo home / Near SFO Airport

4.88 out of 5 average rating, 199 reviews

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

4.99 out of 5 average rating, 338 reviews

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guesthouse in Woodside

Rustic Cabin in the Redwoods

4.99 out of 5 average rating, 108 reviews

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

Delightful Hideaway in San Carlos

4.98 out of 5 average rating, 443 reviews

A spacious bedroom features a comfortable bed with dark gray bedding, flanked by matching bedside tables and lamps. Two large windows allow natural light to fill the room, highlighting the textured wallpaper and organized bookshelf in the corner.

Guesthouse in Belmont

A Comfortable, Clean, & Private Guest House

Guest suite in Foster City

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.

4.99 out of 5 average rating, 98 reviews

New modern 1 bedroom unit

Guesthouse in Redwood City

A spacious bed is positioned in the foreground, adorned with decorative pillows. A soft throw is draped across the bed. The bathroom is visible through an open door, featuring a shower and light tiles. A closet with hangers is also accessible, alongside a small kitchenette.

4.96 out of 5 average rating, 136 reviews

Beautiful private guest studio