Holiday rentals with outdoor seating 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, 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.

4.87 out of 5 average rating, 119 reviews

A light-filled living room features a comfortable white sofa and a stylish armchair, positioned around a wooden coffee table. A modern television is mounted above a decorative stone fireplace. Soft curtains frame the window, enhancing the open feel of the space.

Home in San Mateo

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat

Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

4.83 out of 5 average rating, 281 reviews

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

❤️ 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.

4.92 out of 5 average rating, 350 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.

4.95 out of 5 average rating, 157 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. 🌲

4.78 out of 5 average rating, 101 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.

Guest suite in Emerald Hills

A well-appointed bedroom features a spacious bed with decorative pillows, flanked by bedside tables and lamps. French doors open to a peaceful backyard with views of greenery. A study table and a cozy rug add to the inviting atmosphere.

4.93 out of 5 average rating, 204 reviews

Elegant retreat in Redwood City

NOW with new AC & Heating! Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. Washer/dryer and many other amenities available. This is part of a ~4000 sq ft luxury single family home with a completely separate and private entrance.

4.97 out of 5 average rating, 229 reviews

A light and airy living area features a neutral-toned sofa adorned with patterned cushions. A wooden coffee table with magazines sits in front of the couch, while a modern dining area is visible in the background, showcasing stylish bar stools and large windows.

Guesthouse in Mt. Carmel

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautiful cottage constructed with its own entry, offering beauty, comfort and privacy for your travel needs. Great location for couples, solo & business travelers alike. Cottage well appointed with many travel needs. Expertly maintained and cleaned. Walking distance to Caltrain (.9 mile), bustling downtown Redwood City (.6 mi), boutiques, coffee, restaurants, parks, movies (1.1 mi) & 5 miles to Palo Alto. Easy access to San Francisco, San Jose and the Silicon Valley.

4.99 out of 5 average rating, 121 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

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.

4.93 out of 5 average rating, 295 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.

4.91 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.

4.95 out of 5 average rating, 139 reviews

The exterior of the home is presented with distinct mid-century architecture, featuring large glass windows framed by dark walls. Lush landscaping, including tall grasses and shrubs, surround a smooth stone pathway leading to the entrance.

Home in San Mateo

Calm retreat w/ fireplace & fenced yard

Welcome to your cozy Bay Area retreat - a calm space for relaxed days & fireside evenings. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural - Private backyard w/ fire pit & outdoor dining - Wood-burning fireplace - Kitchen & dedicated workspace w/ fast Wi-Fi - Air conditioning, heating & free parking

Popular amenities for San Mateo outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

Home in Visitacion Valley

A bright and airy kitchen and living area is highlighted by sleek white cabinetry and modern stainless-steel appliances. A comfortable brown sofa faces a round coffee table. Soft pillows are placed on the sofa, and a dining space with four stools is included in the layout.

4.89 out of 5 average rating, 174 reviews

2BR Executive High Ceiling King Suite w/ Bay Views

4.89 out of 5 average rating, 132 reviews

The stylish entrance of the home is framed by a well-maintained garden featuring vibrant flowers and mature greenery. A welcoming porch, with a central front door flanked by sidelights, is complemented by a concrete walkway leading to the inviting entrance.

Home in East Palo Alto

Remodeled Modern Home in Convenient Location

4.83 out of 5 average rating, 224 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.

4.95 out of 5 average rating, 320 reviews

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

4.93 out of 5 average rating, 162 reviews

A spacious room features large windows offering natural light and access to a deck. A cozy bed is complemented by a couch, green bookshelf filled with books, and a simple dining table. Stylish art and decor pieces are arranged along the walls.

Home in Outer Sunset

Bright Slice of the Sunset Private Flat with Deck

4.93 out of 5 average rating, 170 reviews

The modern exterior of the house features a combination of wood and light-colored siding. A covered porch is highlighted by vertical lighting, while large windows provide views of the surrounding landscape. A manicured lawn and driveway contribute to the welcoming entryway.

Home in Mountain View

Upscale Modern House Near Mountain View Downtown

4.97 out of 5 average rating, 236 reviews

Home in San Bruno

Near SFO! Clean&Spacious Hot Tub w/ Stunning Views

4.99 out of 5 average rating, 106 reviews

An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.

Home in Mill Valley

Two Creeks Treehouse

Apartment rentals with outdoor seating

Apartment in Inner Richmond

A modern kitchen space features light-colored cabinetry and a white countertop. A wooden cabinet stands against the wall, and a large window offers a view of the backyard garden. The floor is composed of warm-toned wood, enhancing the room's inviting atmosphere.

4.98 out of 5 average rating, 431 reviews

Beautiful Private Garden Apt. Nr. Golden Gate Park

4.99 out of 5 average rating, 179 reviews

A kitchenette with light wood cabinetry and granite countertops is shown, featuring a dishwasher and various small appliances. A dining area with a vase of fresh flowers is visible, along with a spacious sleeping area beyond, containing a comfortable bed and a wall-mounted TV.

Apartment in San Ramon

Private & clean STUDIO 580/680 Tri-Valley

Apartment in Eureka Valley

A modern living area features a light grey sofa facing a dark television stand. A wooden coffee table sits on a textured rug, surrounded by bookshelves filled with various books. Colorful wall art above the shelves adds visual interest, while ample natural light enters through multiple windows.

4.95 out of 5 average rating, 702 reviews

Relaxed Apartment with a Patio in The Castro

Apartment in Half Moon Bay

A modern kitchen features stainless steel appliances and warm wood cabinetry. Natural light floods the space through skylights and large windows, with views of outdoor greenery. An eat-in dining table with built-in bench seating is complemented by bright blue chairs, creating a cheerful atmosphere.

4.98 out of 5 average rating, 720 reviews

Modern apt steps to beach, trails & downtown HMB

Apartment in Half Moon Bay

A scenic aerial view captures the coastline, revealing sandy shores and the vibrant blue ocean meeting the horizon. Nearby, scattered homes and fields are visible, framed by greenery and gentle hills in the distance, showcasing the natural beauty of the area.

4.96 out of 5 average rating, 219 reviews

Steps to Beach Ocean Retreat / Private Entrance 4

4.97 out of 5 average rating, 166 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

Apartment in Downtown North

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.

4.89 out of 5 average rating, 117 reviews

Studio Apartment with Kitchenette Alcove

Apartment in San Francisco

The living area features exposed brick walls complemented by a modern black leather sofa and a unique wooden coffee table. Two elegant chandeliers provide soft lighting, while a punching bag hangs in the corner. A textured area rug adds warmth to the space.

4.93 out of 5 average rating, 184 reviews

Stylish Apartment, Spectacular Outside Living Room

Condo rentals with outdoor seating

4.96 out of 5 average rating, 225 reviews

Aerial view of the coastal neighborhood shows a two-story condo amid beach houses, highlighting the ocean in the background. The grey building features a distinct entryway with several closely parked cars, surrounded by greenery and well-maintained pathways, suggesting a relaxed coastal environment.

Condo in Pacifica

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

4.96 out of 5 average rating, 100 reviews

The living room features a neutral-colored sofa and a blue futon, complemented by vibrant patterned rug. A wooden coffee table sits at the center, with a decorative plant and an orchid. Walls are adorned with framed artwork, and natural light filters through the window treatments.

Condo in Duboce Triangle

Spacious top 1bd/1ba w/ pvt deck (no cleaning fee)

4.99 out of 5 average rating, 139 reviews

A light-filled living space features an open floor plan with a cozy seating area, including a white armchair and dark gray sofa. A decorative area rug covers the hardwood floor, while a dining table is visible near a modern kitchen with sleek appliances. Natural light streams through large windows.

Condo in Mill Valley

Modern two bedroom, two bathroom Mill Valley Condo

Condo in Pedro Point-Shelter Cove

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.

4.86 out of 5 average rating, 236 reviews

Cabo San Pedro - 1 bed - Stunning Ocean Views

4.98 out of 5 average rating, 286 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

Pacific Heights Home Garden Near Fillmore & Union

4.98 out of 5 average rating, 171 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

4.94 out of 5 average rating, 319 reviews

The Golden Gate Bridge is prominently displayed against a soft sunset sky, with gentle waves lapping on the shore in the foreground. The surrounding hills offer a muted backdrop, creating a serene atmosphere in this coastal setting.

Condo in Cow Hollow

Clean, Private and Safe San Francisco Apartment