Vacation rentals with outdoor seating in Hillsborough

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.

4.94 out of 5 average rating, 854 reviews

A warm and inviting bedroom features a spacious bed with soft peach-colored bedding. A decorative pillow with a friendly message is placed at the head of the bed. A small nightstand with a lamp and a vase of yellow flowers adds a cheerful touch to the space.

Cottage in Daly City

Mini cottage near San Francisco & SF airport

Mini cottage w/ free parking. This tiny cottage (<200sf) is located in our beautiful backyard. It is close to everything. A 15 min drive to downtown San Francisco and SF airport. A 15 min walk to Westlake shopping center & BART station to San Francisco. The beautiful unit has a private entrance, one bedroom with a queen bed and a private bathroom. We provide Wi-fi, towels, instant coffee, tea, and snack. More amenities for you to use: TV, microwave, refrigerator, hair dryer & electric kettle.

5 out of 5 average rating, 140 reviews

A modern living area features a sectional sofa complemented by a glass coffee table. Large sliding doors provide natural light and a view of the outdoor space. A sleek fireplace adds warmth to the room, with a stylish area rug enhancing the comfortable setting.

Home in Miramar

Fabulous Beach Get Away - Brand New Beach House

Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

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.

4.98 out of 5 average rating, 443 reviews

A cozy living area features a gas fireplace, providing warmth. A television is mounted above, and natural light enters through two windows. A round red rug is positioned on the hardwood floor, with a light-colored sofa and a dark chair visible, creating an inviting space.

Cottage in Woodside

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Guest suite in Half Moon Bay

A cozy outdoor seating area features two rattan chairs positioned on a deck. A small table rests between them, with a scenic ocean view visible in the background. Sunrise colors illuminate the sky, and a vibrant pink flamingo adds a playful touch to the greenery.

4.96 out of 5 average rating, 358 reviews

Oceanview Penthouse, Stylish, Walking to Beach

A perfect romantic getaways to this stylish indoor/outdoor Penthouse! We are 10 mins walk to beaches and 15 mins walk to award winning restaurants. There are a lot of fun activities: spending your days on the beach, exploring the hiking, biking, golfing, surfing, kayaking, paddle boarding or just simply kick back relax in this quiet and picturesque property with a panoramic ocean view, enjoying the sunset and the beautiful garden. We are 30 mins to SF or 60 mins to Santa Cruz.

4.98 out of 5 average rating, 198 reviews

A sweeping landscape showcases vibrant orange poppies in the foreground, with rolling hills and the Pacific Ocean visible in the background. The scene captures a blend of natural beauty, framed by lush greenery and distant coastal views.

Guest suite in Linda Mar

Cozy, modern 1-bedroom with backyard ocean view!

Fall in love with this modern & sunny, 1 bedroom, 1 bath apartment with walk-in shower, refrigerator, TV, coffee/tea, & fast internet. First-floor unit (430 sq ft) with private entrance has views of nature & access to a peaceful backyard—steps from an awe-inspiring view of the Pacific Ocean. This one-of-a-kind, tranquil getaway offers the best of the Bay Area at your fingertips! Walk to hiking trails, drive 5-min. to the beach, & 20-min. to San Francisco or SFO airport.

4.99 out of 5 average rating, 122 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.

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.

Guesthouse in Park Pacifica

A well-lit guestroom features a queen-size bed with floral bedding. A spacious loveseat sofa is positioned near a sliding glass door that opens to the backyard. A small coffee table rests in front of the sofa, and a portable air conditioner is visible in the corner.

4.97 out of 5 average rating, 520 reviews

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

4.99 out of 5 average rating, 118 reviews

A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.

Home in Montara

Sea Wolf Bungalow

If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.

4.95 out of 5 average rating, 139 reviews

A vibrant yellow dining table set for eight is positioned in a spacious open-plan area, surrounded by natural light from large glass doors. A soft, textured light fixture hangs overhead, complementing the modern aesthetic. The backdrop features a landscaped outdoor space visible through the glass.

Home in San Mateo

Calm 3BR retreat w/ enclosed atrium

Welcome to a calm Bay Area retreat perfect for cozy evenings & easy indoor-outdoor living! - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Wood-burning fireplace & fenced backyard w/ fire pit - Enclosed atrium w/ custom mural - Kitchen, dining area & dedicated workspace - Single-level layout w/ private entrance - Free parking, Wi-Fi & in-unit laundry

Popular amenities for Hillsborough outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.88 out of 5 average rating, 120 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

4.97 out of 5 average rating, 138 reviews

Home in Linda Mar

Walk to Beach - Remodeled Coastal Home Safe Town

4.83 out of 5 average rating, 283 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

4.94 out of 5 average rating, 183 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

4.93 out of 5 average rating, 164 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

4.94 out of 5 average rating, 409 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 Work & Wellness Oasis

4.8 out of 5 average rating, 336 reviews

Home in Serramonte

San Francisco Oasis / Patio / Garage & Office /16+

Superhost

A spacious living area displays light-colored marble flooring and modern furnishings. A round coffee table with a small plant sits in front of a cozy green seating option. A Smart TV is positioned across from a dining table surrounded by four chairs. Soft lighting illuminates the space.

Home in Visitacion Valley

4.85 out of 5 average rating, 147 reviews

Luxe High Ceiling King Suite w/ Bay Views

Apartment rentals with outdoor seating

4.95 out of 5 average rating, 237 reviews

A private deck offers views of the ocean and surrounding greenery. The clear blue water is visible against the horizon, framed by tall trees and shrubs. Bright yellow outdoor furniture adds a pop of color to the serene setting.

Apartment in Montara

Montara Ocean View Suite

The living area features a modern design with a gray sectional sofa and vibrant orange ottomans. A wall-mounted television is positioned on a white unit, while natural light filters through large windows leading to a private outdoor space.

4.9 out of 5 average rating, 455 reviews

Coastal Zen Cottage - Walk To Beach!

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, 163 reviews

Modern Oceanview 2-Bed Apartment Home

4.99 out of 5 average rating, 174 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 Longfellow

The Cozy Casita 2

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, 706 reviews

Relaxed Apartment with a Patio in The Castro

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, 723 reviews

Modern apt steps to beach, trails & downtown HMB

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

Condo rentals with outdoor seating

4.96 out of 5 average rating, 177 reviews

The exterior of the beach condo is captured from above, showcasing the spacious driveway and the contrasting grey tones of the building's facade. Ocean views are visible in the distance, along with neighboring houses and the coastal environment.

Condo in Pacifica

Game room, 20 min to SF, hot tub, beach 1 block

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

4.98 out of 5 average rating, 287 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, 321 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

4.98 out of 5 average rating, 61 reviews

A spacious living area features a large, modern couch facing a wall-mounted TV. Natural light fills the room from windows overlooking the city. A round coffee table sits on polished wood flooring, complemented by a cozy fireplace and a dining space with stylish bar stools in the background.

Condo in Dolores Heights

Modern Home with Scenic Views in Mission Dolores