Vacation rentals with outdoor seating in Hillsborough

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Top-rated outdoor seating rentals in Hillsborough

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Guest favorite

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)

Oct 2 – 9

G$113,586 GYD per night

Guest favorite

Guest suite in El Granada

5.0 out of 5 average rating, 328 reviews

Private Modern Coastal Retreat With Ocean Views

Modern private studio suite, under a mile from the beach, hiking trails, Pillar Point Harbor, restaurants, activities & Maverick’s Beach. 4 miles from historical Half Moon Bay, 30 mins from San Francisco & 25 mins from the 280-freeway; leading to Silicon Valley. Enjoy hill top ocean views from your private garden while enjoying your morning coffee or afternoon glass of wine. Fully equipped for a long term stay or weekend getaway. Ideal for 1-2 adult guests only. We can not accommodate children.

Jun 26 – Jul 3

G$40,482 GYD per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Oct 2 – 9

G$70,171 GYD per night

Guest favorite

Cottage in Woodside

4.97 out of 5 average rating, 343 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!

Dec 2 – 9

G$37,744 GYD per night

Guest favorite

Apartment in Burlingame

4.97 out of 5 average rating, 404 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.

Dec 28 – Jan 4

G$35,627 GYD per night

Superhost

Guest suite in Pacifica

4.83 out of 5 average rating, 244 reviews

Beach Getaway with Jacuzzi | Forest View| Near SF

Great location at the base of Montara Mountain with fantastic hiking and biking trails! Pacifica Beach, restaurants and shops are just a 15 minute walk along a beautiful paved path. Our spacious suite is part of a main house and has a separate entrance with private use of our Jacuzzi, huge deck and backyard. We are in a quiet neighborhood with plenty of free parking. Perfect place to make as your base for sightseeing or a business trip. San Francisco and the airport are 20 minutes by car.

Mar 12 – 19

G$18,725 GYD per night

Guest favorite

Guest suite in Belmont

4.95 out of 5 average rating, 103 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. 🌲

Jun 1 – 8

G$26,481 GYD per night

Guest favorite

Home in Burlingame

4.91 out of 5 average rating, 150 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.

Jul 12 – 19

G$32,118 GYD per night

Guest favorite

Guesthouse in Pacifica

4.98 out of 5 average rating, 372 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!

Dec 2 – 9

G$27,563 GYD per night

Guest favorite

Guest suite in Emerald Hills

4.91 out of 5 average rating, 148 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.

Nov 11 – 18

G$25,773 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 383 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.

Mar 28 – Apr 4

G$24,277 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 814 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.

Nov 19 – 26

G$27,820 GYD per night