
House holiday rentals in Hillsborough
Find and book unique houses on Airbnb
Top-rated house rentals in Hillsborough
Guests agree: These houses are highly rated for location, cleanliness and more.

Stairway to Heaven - 2 bedroom
PLEASE NOTE, we live in a 3 story home and this unit is on the lower level of our home. Also available in a 1 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

Pet Friendly, Gem of a House 5 mins to beach & SF
Dog-friendly, beautifully refurbished Doelger architectural oasis minutes from SF, the beach, Bart, several golf courses and SFO. Quiet, safe neighborhood with lots of parking and character. Large shopping center within three blocks with Trader Joes, 24 Hour Walgreens, Safeway, Starbucks, a Gym which offers day passes, Yoga studio and lots of dining choices. Cook in fully appointed chef’s kitchen, gather around the fire pit in the backyard, or melt your stress away in the deep-soaking tub.

Cute beach house with skylights and open spaces
Located in Pacifica, CA a block away from the ocean shoreline(3 mins stroll to the shoreline). You can hear the gentle sounds of the ocean on our quiet street. With xeriscaping characterized by local plants and bougainvillea, our little blue beach house has a large front porch with lots of sunlight to relax in and a small backyard deck to enjoy the warm weather. Inside, the living room has 14' ceilings with skylights. The guest room is fully furnished as are the kitchen and master bedroom.

Andulore Cottage - Walk to Burlingame Dining/Shops
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.

Hot Tub Home in Pacifica Free Parking /Beach/SFO
🏡 Your Perfect Getaway Near San Francisco & SFO – Quiet, Convenient, and Comfortable! If you like to stay close to the city yet have a feel of being on a gateway, this is your place. Located in the quiet Park Pacifica, our home is 18miles from downtown San Francisco & 11miles from SFO. 6 mins drive to beaches, shops, and the iconic Highway 1 road trip route. Whether you're here to explore or relax, this is the ideal spot to unwind. Free parking is available right in front of the house.

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley
Located in the SF Bay Area Peninsula with 180-degree panoramic views of the Bay Area, 3,012 square feet, 4 bedrooms and 3 full bathrooms. Located on the upper level is the kitchen, dining room, TV room, and spacious living room. Lower level has four bedrooms. Must be able to climb stairs. Refinished hardwood floors and carpet in the bedrooms. Backyard extends into multiple decks, including BBQ grill and hot tub. Located between San Francisco and Silicon Valley. Very close to SFO.

Luxury Ocean Front & Harbor View Home
Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Half Moon Bay, this stunning property is the perfect destination for your next coastal retreat. The two-bedroom, three-bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Half Moon Bay throughout the common areas and bedrooms. This is the ultimate in coastal luxury, featuring modern appliances and an open floor plan through all the common areas.

Bright retreat w/ fire place & atrium
Welcome to your Bay Area retreat - a thoughtfully renovated 1956 Joseph Eichler home offering mid-century charm and comfortable spaces for relaxing or working remotely. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural & red maple tree - Private backyard - BBQ grill, fire pit & outdoor dining - Wood-burning indoor fireplace & open-concept living - Dedicated workspace & Wifi - Kitchen, air conditioning, washer/dryer & free parking

Serene Modern Home with Yard & Parking
This spacious, tastefully decorated and full of natural light large house is a perfect combination of comfort and style. The house is recently renovated and has got everything to accommodate all your needs for a perfect stay. Convenient strategic location and easy commute to SF, Silicon Valley, BART and Airport, full amenities, parking, safe and quiet neighborhood, professionally managed, immaculately clean and more. Book now before someone else does!

Cozy San Mateo home / Near SFO Airport
Looking for the perfect short-term rental in the Bay Area? This fully furnished 3-bed, 2-bath home in San Mateo is ideal for families, business travelers, and vacationers. Located just six blocks from vibrant downtown, you’ll be steps from ethnic restaurants, boutique shopping, and local charm. Just 10 minutes from SFO airport. Easy access to San Francisco and San Jose. This inviting home is your ideal base for experiencing the best of the Peninsula.

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready
Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities

Luxury Silicon Valley Wellness and Work Oasis
Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.
Popular amenities for Hillsborough house rentals
House rentals with a pool

Beautiful Large 4BR Home with POOL

Pool, Hot tub SFO, Napa, Clean Home

Large Home in Palo Alto, 5 bedrooms, Pool

Little Poolside House near Downtown Mountain View!

Waterfront home w/ private dock and pool

3 BR Home on Vineyard nr Palo Alto & Stanford

Beautiful 4 Bedroom Hillside Retreat

The Hacienda- Santa Cruz Mountain Ridgetop Retreat
Weekly house rentals

Scenic Sequoia: A Chic California Hillside Retreat

Scenic Retreat w/ AC Hidden Gem Near SFO/SF/Beach

Serene Bayview 4BR · Single-Level · 1Gbps WiFi

Cozy Half Moon Bay with Mountain and Oceanview

Bright Spanish-style home in Burlingame

Charming Burlingame Beauty!

Downtown 3B/3b kids friendly home

Renovated 3b1.5b San Mateo hill near SFO/Stanford
Private house rentals

San Mateo Sanctuary | Central • Near SFO • Quiet

Brand New Executive Home

Miramar Penthouse Coastal Elegance in the Heart of

Spectacular California Ocean Front Home!

Hidden & Quiet Home Up on the Hill w/ Private Yard

Eagle Hill Craftsman

Spacious, Remodeled 2BR Duplex Unit by Downtown SM

SanMateo Comfortable 2BR Home/WiFI & Free Parking
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $282 AUD | $315 AUD | $315 AUD | $284 AUD | $360 AUD | $360 AUD | $353 AUD | $284 AUD | $281 AUD | $352 AUD | $352 AUD | $353 AUD |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°C |
Quick stats about house rentals in Hillsborough

Total holiday rentals
Explore 60 holiday rentals in Hillsborough

Verified guest reviews
Over 3,180 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Hillsborough holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hillsborough rentals

4.9 Average rating
Hillsborough stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Northern California Holiday rentals
- San Francisco Bay Area Holiday rentals
- San Francisco Holiday rentals
- Gold Country Holiday rentals
- Central California Holiday rentals
- San Francisco Peninsula Holiday rentals
- San Jose Holiday rentals
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- Santa Barbara Holiday rentals
- Wine Country Holiday rentals
- South Lake Tahoe Holiday rentals
- Rentals with outdoor seating Hillsborough
- Fitness-friendly rentals Hillsborough
- Family-friendly rentals Hillsborough
- Apartment rentals Hillsborough
- Rentals with a fireplace Hillsborough
- Pet-friendly rentals Hillsborough
- Rentals with pools Hillsborough
- Rentals with a patio Hillsborough
- Rentals with a fire pit Hillsborough
- Rentals with a hot tub Hillsborough
- Rentals with a washing machine and dryer Hillsborough
- House rentals San Mateo County
- House rentals California
- House rentals United States
- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Oracle Park
- Capitola Beach
- Muir Woods National Monument
- Golden Gate Bridge
- Rio Del Mar Beach
- SAP Center
- Santa Cruz Beach Boardwalk
- Mission Dolores Park
- Seacliff State Beach
- Pier 39
- Twin Peaks
- Henry Cowell Redwoods State Park
- Six Flags Discovery Kingdom
- University of California-Berkeley
- Levi's Stadium
- Palace of Fine Arts
- Montara Beach
- Winchester Mystery House
- Bolinas Beach
- California’S Great America




