Holiday rentals with outdoor seating in San Mateo

Guesthouse in Redwood City

A modern kitchen is highlighted by a spacious granite countertop island with four wooden stools. Natural light pours in through a large window overlooking the garden, illuminating stainless steel appliances and cabinetry. Plants add a touch of greenery to the inviting space.

4.99 out of 5 average rating, 125 reviews

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.

Guesthouse in Redwood City

A shaded porch area features stone flooring and is bordered by lush greenery. Two outdoor chairs and a small table are positioned on the left side, providing a serene spot for relaxation. The entrance to the studio is visible through large glass doors.

4.95 out of 5 average rating, 213 reviews

Charming Studio

Small private studio with queen bed with Tempur-pedic mattress. It features an extra-large storage drawer for essentials. portable closet, fully stocked kitchen, & bathroom, backyard, porch, free parking and high speed internet. The studio is ideal for business travelers. It's centrally located between SF and Silicon Valley. easy access to highways 280 and 101. Public transportion is within walking distance as well as downtown San Carlos and RWC. FYI: The yard is shared and three dogs.

4.95 out of 5 average rating, 116 reviews

Home in Redwood City

Cozy & Fully Equipped Studio

Welcome to your perfect retreat! Our studio is fully equipped, modern, and super comfortable, offering all the amenities for an unforgettable stay. Whether you’re traveling for business or leisure, this space provides the ideal balance between comfort and convenience. 🛋 Cozy living area: Beautifully decorated with a comfortable sofa, TV 🍽 Fully equipped kitchen 🌿 Private patio: A perfect outdoor space to relax and enjoy fresh air. 🚗 Private parking with independent entrance self check in

4.92 out of 5 average rating, 195 reviews

Andulore Cottage - Walk to Burlingame Dining/Shops

Welcome to Andulore Cottage! Remodeled home in great location in quiet neighborhood. Walk to Burlingame Avenue shops, restaurants and Caltrain Station! This 1944 WWII era cottage has been lovingly restored, updated and renovated while preserving historic detail and charm throughout. Interior decor of this home is styled mid-century transitional. There are three bedrooms, living room, dining room, kitchen, and spacious backyard with beautiful patio with brick BBQ and fireplace.

4.78 out of 5 average rating, 109 reviews

The studio features vaulted wooden ceilings and a spacious layout. A king bed is positioned near a large window, providing natural light. A smart TV is placed on a stand, while a kitchenette can be seen in the background, equipped with modern appliances.

Guest suite in San Mateo

246C - Large Studio w/ Kitchenette, Laundry & Deck

This is a spacious, modern, and newly remodeled studio unit in our beautiful home located in the center of Hillsdale. This studio features a king bed, smart TV, private bathroom, large kitchenette and wet bar, in-unit laundry, and a spacious SHARED deck with the main unit. It is 2 blocks from San Mateo Medical Center, and only a mile away from Hillsdale Shopping Center & Traders Joe's. There are many restaurants & shops nearby. This studio is accessed from the backyard deck.

A private backyard scene features a wooden deck with a circular table and an outdoor sofa amid lush greenery. Tall grasses sway gently in the breeze, while nearby trees provide a natural backdrop under a clear blue sky.

4.95 out of 5 average rating, 147 reviews

Mid-century retreat - fire pit and backyard

Welcome to a beautifully renovated 1956 Eichler home in the San Mateo Highlands - a distinctive mid-century space with soaring ceilings, natural light, and a private backyard made for gathering. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated private office w/ door - Wood-burning fireplace & full kitchen w/ gas stove - 20 mins to SF | 15 mins to SFO | Near Caltrain

4.98 out of 5 average rating, 255 reviews

The exterior of the cottage features a stone-accented porch with a wooden chair, framed by lush greenery and flowering plants. A pathway of stones leads from the well-kept lawn to the entry, where large double doors invite guests inside.

Cottage in San Carlos

Carmelita Creek House

The creek house is on a beautiful tree lined street, walking distance to downtown San Carlos. The house is a spacious one bedroom cottage with designer finishes and vaulted ceilings. You will be surrounded by mature redwoods and nature overlooking a year round creek. Amenities include a full sized kitchen, workspace, washer/dryer, fast WiFi, cable TV and a gas fireplace. Please note the cottage is located behind our main home and is accessed via several steps.

4.99 out of 5 average rating, 145 reviews

An inviting deck area features two white lounge chairs adorned with pillows, positioned near a door leading into the studio. A light-colored rug lies in front of the entrance, while a wooden railing offers a view of the surrounding greenery.

Guesthouse in San Carlos

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.

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.

4.83 out of 5 average rating, 115 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.

4.93 out of 5 average rating, 312 reviews

Home in Foster City

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.

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.

4.9 out of 5 average rating, 128 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.

4.89 out of 5 average rating, 142 reviews

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready

Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities

Popular amenities for San Mateo outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.84 out of 5 average rating, 232 reviews

A bright living space features a red sofa and a wooden coffee table, complemented by a stylish side table with a lamp. A black futon is positioned nearby. Shelving displays various decorative objects, while large windows allow natural light to illuminate the room.

Home in Redwood City

Heart of Silicon Valley Studio/Cottage

Home in South San Francisco

The dining area features a large, rectangular table surrounded by four upholstered chairs, providing a comfortable setting. Natural light floods in through large windows, showcasing a view of the landscape. A decorative wall clock and a framed artwork add character to the space.

4.94 out of 5 average rating, 348 reviews

★EV+★Hillside SFO View★Home Theater★Pool Table

4.93 out of 5 average rating, 113 reviews

A dining area features a large wooden table surrounded by simple chairs. Potted plants are arranged by ample windows that allow natural light to fill the space. A cozy window seat is positioned along the wall, adding to the inviting atmosphere of the room.

Home in Berkeley

Modern Vintage Garden Bungalow

4.98 out of 5 average rating, 99 reviews

A bright living area features a comfortable dark sofa and two light-colored armchairs beside a round coffee table. A flat-screen television is mounted above a traditional fireplace. Open French doors lead to a bright adjoining room, while a patterned rug adds texture to the wooden floor.

Home in Burlingame

Charming Burlingame Beauty!

4.93 out of 5 average rating, 201 reviews

A private fenced backyard features comfortable seating, including a sectional sofa and coffee table. Soft lighting from cafe lights enhances the outdoor environment. Lush greenery surrounds the space, providing a natural backdrop, with a welcoming mat positioned at the entry.

Home in Pacifica

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard

Home in South San Francisco

The image captures a serene garden view from a covered porch. Vibrant red maple trees and lush greenery frame a winding path, creating a tranquil atmosphere. Comfortable wicker chairs are positioned on the porch, offering a peaceful spot to enjoy the natural surroundings.

4.93 out of 5 average rating, 183 reviews

Secluded Garden Retreat between SFO & SF

4.96 out of 5 average rating, 183 reviews

A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.

Home in Half Moon Bay

Stairway to Heaven - 2 bedroom

4.94 out of 5 average rating, 441 reviews

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

Luxury Silicon Valley Wellness and Work Oasis

Apartment rentals with outdoor seating

4.89 out of 5 average rating, 298 reviews

A hot tub is positioned on a wooden deck, surrounded by lush greenery and tall trees. The ocean view stretches into the horizon, creating a serene backdrop under a clear blue sky.

Apartment in Muir Beach

Amazing Welcoming Unique Ocean Home

Apartment in Half Moon Bay

An aerial view captures the expansive coastline of Half Moon Bay, with golden beaches meeting the turquoise ocean. The landscape features a blend of residential areas, fields, and distant rolling mountains, creating a serene and open atmosphere.

4.99 out of 5 average rating, 106 reviews

Steps to Beach Ocean Retreat / Private Entrance 2

Apartment in Half Moon Bay

A spacious living area is shown, featuring a modern desk and a unique chair. Natural light fills the room through large windows, which are complemented by dark curtains. Decorative elements include a wall clock and a circular mirror, enhancing the overall inviting feel.

4.99 out of 5 average rating, 185 reviews

Modern Oceanview 2-Bed Apartment Home

4.99 out of 5 average rating, 196 reviews

A bright and modern kitchen area features dark cabinetry and a coffee station, accompanied by a patterned rug on the floor. A breakfast bar with two stools is visible, and the open layout connects to a cozy living space that showcases colorful furnishings and artwork.

Apartment in Oakland

The Cozy Casita 2

4.9 out of 5 average rating, 314 reviews

A modern floating condo is shown, featuring a mix of wooden and glass exteriors. The structure is connected by a sturdy ramp leading to the water. Soft lighting from a nearby lamp enhances the tranquil evening atmosphere, with a colorful sunset reflecting off the water.

Apartment in Marin City

Floating condo 'A' on Sausalito's Richardson Bay.

4.91 out of 5 average rating, 465 reviews

A spacious private living room is furnished with a sleek black sofa bed and a round coffee table. A Smart TV is positioned against a white media console. Light-colored walls are adorned with framed artwork, and abundant natural light filters through large windows.

Apartment in Daly City

Admire Commanding City Views from an Airy Abode with Parking

4.99 out of 5 average rating, 201 reviews

Apartment in San Rafael

Mount Tamalpais View — the Heart of Marin County

4.84 out of 5 average rating, 498 reviews

A vibrant yellow wooden gate features a circular cutout, framing a view of lush greenery beyond. A fruit tree is visible through the opening, enhancing the connection to the surrounding garden.

Apartment in Alameda

Secret Garden Cottage

Condo rentals with outdoor seating

4.9 out of 5 average rating, 121 reviews

A bright and airy living space features a unique circular rug with warm tones and a modern dining table surrounded by stylish chairs. Decorative plants enhance the natural light, while a wall-mounted TV and sound system provide entertainment options.

Condo in Potrero Hill

Potrero Penthouse | 4 Sunny Decks + Skyline Views

4.97 out of 5 average rating, 258 reviews

Condo in Pacifica

Twenty minutes to SF, one block to beach, fire pit

4.82 out of 5 average rating, 198 reviews

An outdoor patio features a modern fire pit with glowing stones, surrounded by warm ambient lighting. A secluded seating area with draped fabric offers a cozy space, while wooden paneling adds texture to the wall. Softly illuminated canopies enhance the inviting atmosphere.

Condo in San Francisco

Private Modern Retreat - Patio, Fire Pit, Hot Tub+

4.9 out of 5 average rating, 204 reviews

The living area features bright white walls and elegant wood flooring. A comfortable white sofa is positioned next to a round marble dining table. A TV is mounted on the wall while a fireplace adds to the cozy ambiance. Large windows allow natural light to fill the space.

Condo in Stinson Beach

Sunset Beach Retreat

4.98 out of 5 average rating, 322 reviews

A private garden area features modern seating arrangements, including a long sectional and armchairs surrounding a fire pit. Lush greenery and flowering plants add color to the space, while a wooden fence provides privacy. The sky above is bright with scattered clouds.

Condo in Pacific Heights

Elegant Garden Suite Steps to Lafayette Park

4.86 out of 5 average rating, 258 reviews

A deck overlooking the coastline features two red chairs positioned to take in expansive views of the Pacific Ocean and surrounding landscapes. The railing adds a contrasting element, while a small table sits between the chairs, enhancing the tranquil setting.

Condo in Pacifica

Cabo San Pedro - 1 bed - Stunning Ocean Views

4.98 out of 5 average rating, 181 reviews

A modern kitchen features stainless steel appliances, including a large refrigerator and a five-burner gas stove. White cabinetry and light wood counters provide a bright atmosphere. Ample workspace is available, along with under-cabinet lighting that highlights the tiled backsplash.

Condo in Alameda

Cozy condo in the heart of Alameda