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

Cottage in Daly City

4.93 out of 5 average rating, 792 reviews

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.

Guest favourite

Guest suite in Daly City

4.96 out of 5 average rating, 592 reviews

5 min to SF, Luxurious couple retreat,spa,balcony

Unwind from your day and relax in the jet tub and massage recliner chair in this luxurious 450 sqf master suite w/vaulted ceiling, crown moldings and a huge onyx marble bathroom w/skylight. The suite sets far back in the green garden w/private entrance & balcony in safe, tranquil SF suburban. Close to scenic Highway 1 & beaches w/ many gourmet restaurants nearby. Free parking on the driveway. A comfy memory foam mattress, down comforter and soothing lavender epsom salt bubble bath are provided.

Guest favourite

Flat in San Francisco

4.91 out of 5 average rating, 182 reviews

Garden studio oasis w/ kitchenette & private entry

Cosy, comfortable, and quiet unit with direct access to a lovely garden. 10 min. from the airport, 30 min. from downtown via express bus. Well-connected, sunny neighborhood. Free street parking. Views of the bay, mature redwood trees, easy to get to attractions. Walking distance to bustling food corridor, with restaurants, cafes, grocery stores, ATMs, pharmacy, salons, library, and more. Blocks from largest park in the city with sweeping views, historic greenhouses, and unique Freeway Greenway.

Guest favourite

Guest suite in San Mateo

4.92 out of 5 average rating, 332 reviews

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.

Guest favourite

Flat in San Mateo

4.94 out of 5 average rating, 213 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!

Guest favourite

Home in San Mateo

4.91 out of 5 average rating, 162 reviews

Andulore Cottage - Near Burlingame Ave - Remodeled

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.

Guest favourite

Guest suite in Belmont

4.94 out of 5 average rating, 142 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. 🌲

Guest favourite

Home in Burlingame

4.92 out of 5 average rating, 178 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.

Top guest favourite

Guest house in Pacifica

4.97 out of 5 average rating, 472 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!

Guest favourite

Home in San Mateo

4.94 out of 5 average rating, 124 reviews

Mid-Century Retreat w/ Fire Pit & Private Backyard

Welcome to your stylish Bay Area retreat—where mid-century design meets modern comfort. This spacious Eichler home is perfect for families, remote workers, and weekend getaways. • 3 bedrooms, 2 full baths (sleeps 6) • Private office with fast Wi-Fi • Open-concept living, full kitchen • Enclosed atrium with custom mural • Private backyard with BBQ, fire pit, outdoor dining • Peaceful neighborhood, 20 mins to SF, 15 mins to SFO

Guest favourite

Campervan/Motorhome in Half Moon Bay

4.98 out of 5 average rating, 128 reviews

Airstream Beach View (Dream) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Surf views with large windows. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, A/C and fully stocked kitchen. Full bathroom with shower. If this one is booked, there are three other equally similar Airstreams on the property.

Top guest favourite

Flat in Burlingame

4.97 out of 5 average rating, 443 reviews

Home away from home in wonderful Burlingame

It's my honor to be your host and I will try to make your stay really great. I provide suggestions of things to do but feel free to ask for advice! Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price has been increased to reflect that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.