Holiday rentals with outdoor seating in Hillsborough

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Hillsborough

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Guest favourite

Home in San Mateo

4.93 out of 5 average rating, 106 reviews

Lovely Mid-Century home near SF, SFO, & Peninsula

Walk through the enclosed atrium sporting a custom mural and stunning red maple in this home dating back to 1956. The spacious house boasts mid-century furniture and art with a wall of glass overlooking the deck with a backdrop of fruit trees. Spacious 2 bedrooms & den with TV converts to a sofa bed. You also have a private office if you're working from home, right off the atrium. Enjoy a lovely dinner in back garden on a cool summer night. Though we love children, our home is not childproof, and we prefer not to host children under 12 years of age, thank you for understanding. This home was built in 1956 by Joseph Eichler and completely remodeled in 2017 with the goal of staying true to its original Mid-Century design while updating the house for modern living. It features a collection of beautiful Mid-Century furniture and art made by the owner and friends. Guests enter through an enclosed atrium that sports a custom mural and stunning red maple. The back yard features a large dining area with a backdrop of fruit tree and a spacious deck overlooking thousands of acres of open space and the Coastal Range. This home has two bedrooms with queen size beds and one bedroom with a full size sofa-bed. The master bedroom has an en suite bathroom with walk-in shower, the other two rooms share a bathroom with a deep tub. There is a spacious, well lit office for your use. One of the best features of this home is it's great room with a wood-burning fireplace, dining room, and kitchen--perfect for entertaining a small group. The backyard features an 8 person outdoor dining table and 6 burner BBQ for your use, as well a large outdoor sofa surrounding a fire pit. The front atrium is another well lit modern get away where you can to sit back and enjoy nature and art. Guests will have access to the entire property including the house and gardens. There is a washer and drier for guest use in the garage. I have a co-host who will be there for you 24/7. The house is in the Highlands neighborhood, which was developed by Joseph Eichler in the mid-1950s. The community center across the street from the property features a great playground for children. San Francisco Airport is 15 minutes away. - Caltrain (Goes up and down to San Francisco and San Jose) - BART (Goes to Downtown San Francisco and East Bay) - Lyft (Use referral code JEN573431) - Uber (Use referral code jcc271ue) Parking in the drive way only (no garage use for cars). TV in one of the bedrooms, not the living room. No parties or events allowed. No curtains in two of the bedrooms, but no one can see into these room as a building wall hides them. 20 minutes to downtown San Francisco We take cleaning in this climate very seriously, we are in full compliance with the cleaning guidelines approved by WHO (Worldwide Health Organization) CDC (Center for Disease Control) and the EPA (Environmental Protection Agency)

3–10 Sep

$748 SGD per night

Guest favourite

Flat in San Mateo

4.94 out of 5 average rating, 184 reviews

Fabulous apartment in downtown San Mateo

Relax away from the hustle of the city in your apartment in downtown San Mateo. Located only two blocks from the San Mateo Caltrain, you can get to or from SF or SJ in 30 minutes. Our home has a separate entrance for the guest apartment on the second floor. Tuck yourself away in the California King sized bed, or explore downtown on foot. With over 100 restaurants in walking distance, you will not have a shortage of delicious dining. Eat out or enjoy a meal in the comfort of your home. Welcome!

13–20 May

$165 SGD per night

Guest favourite

Cabin in Woodside

4.97 out of 5 average rating, 342 reviews

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!

3–10 Aug

$246 SGD per night

Guest favourite

Cottage in Daly City

4.94 out of 5 average rating, 661 reviews

Mini cottage near San Francisco & SF airport

Mini cottage w/ free parking. This small cottage 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 and 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.

20–27 Sep

$101 SGD per night

Guest favourite

Flat in Burlingame

4.97 out of 5 average rating, 403 reviews

Home away from home in wonderful Burlingame

We've been hosting for 11 years and love it. It's my honor to be your host and I will try to make your stay really great. I provide a list of summer events/festivals, farmer's markets, local "music in the park", and other suggestions but feel free to ask for advice! We donate 5% of all earnings to Airbnb.org to provide support in local, national and global housing emergencies. *** Please see House Rules at the end of the listing description to ensure our apartment will work for you.

31 Jul – 7 Aug

$259 SGD per night

Guest favourite

Home in Moss Beach

4.91 out of 5 average rating, 114 reviews

Studio with Private Entrance / Patio / Hot Tub

Relax in this peaceful, private studio after a fun day at the beach or exploring our beautiful coast. 1/2 mile from beach & 7-minute drive to Half Moon Bay or Pacifica! Features include a private fenced patio with access to hot tub, new hybrid queen bed, 55" TV, ceiling fan, central heat/air, kitchenette and private bath/separate shower. The new loveseat is also a comfy sleeper - $50.00 for each additional guest, up to 2 with 4 guests max in unit. Note: EV Charger is $25.00 per use.

20–27 Apr

$188 SGD per night

Guest favourite

Guest suite in Belmont

4.95 out of 5 average rating, 102 reviews

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. 🌲

24–31 Aug

$150 SGD per night

Guest favourite

Home in Burlingame

4.91 out of 5 average rating, 149 reviews

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

19–26 Aug

$206 SGD per night

Guest favourite

Guest house in Pacifica

4.98 out of 5 average rating, 370 reviews

NEW Private Studio! Close to SF/SFO/Beach Sanitize

Built in 2020, our guesthouse is a perfect place for romantic getaways and road trips. It has a private entrance, smart lock, whole room UV light sanitizers, hotel-quality bedding, brand-new furniture, and the latest interior designer selection. 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!

24–31 Aug

$192 SGD per night

Guest favourite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 146 reviews

Elegant retreat in Redwood City

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. All furnishings are selected by a professional decorator and routinely upgraded. This is part of a ~4000 sq ft luxury single family home with 2 completely separate and private entrances.

25 Nov – 2 Dec

$168 SGD per night

Guest favourite

Guest house in La Honda

4.95 out of 5 average rating, 382 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

22 Feb – 1 Mar

$158 SGD per night

Guest favourite

Guest house in Hillsborough

4.95 out of 5 average rating, 810 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

1–8 Dec

$190 SGD per night