
House vacation rentals in Hillsborough
Find and book unique houses on Airbnb
Quick stats about house rentals in Hillsborough

Total vacation rentals
Explore 60 vacation rentals in Hillsborough

Verified guest reviews
Over 2,530 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Hillsborough vacation 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!
Top-rated house rentals in Hillsborough
Guests agree: these houses are highly rated for location, cleanliness, and more.

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard
Home is dog friendly! Cozy 2 bedroom [Queen Beds] home, one bath, centrally located, private entry, lots of natural light, private fenced backyard, cafe lights, space for kids, pets to run around. Beach access trail on Mori Point 1/2 block away, 1/2 mile walk down the trail to Sharp Park Beach, you may see whales from the shore! Sharp Park Golf Course is one block walking distance. 15 min to SFO | 20 min to downtown San Francisco, private driveway and lots of free street parking available!

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.

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.

Two Creeks Treehouse
Looking for a healthy dose of tranquility and adventure at your doorstep? Over 100 steps from the road below, this 'treehouse' is perched above it all and horizontally oriented on a steep lot between two creeks. The all glass façade creates dramatic views of the redwoods, Mt. Tam and across downtown Mill Valley to Blithedale Ridge. Anchored to granite the house sits on handmade stone walls from rock harvested on the property during construction in the 1960s. Truly a one of a kind stay.

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.

Sunlit 2B1B house w/ Deck & Garden on Belmont hill
Escape to this peaceful retreat with new furniture, beautiful garden and nice views over Belmont hill! Luxury like your own home: - Leather sofa & Smart TV - Complete cookware and dining essentials - Big deck with a dining set - Large Private Backyard for relaxation Convenience: - Surrounded by various attractions - San Francisco and San Jose are both half-an-hour away - Easy access to Caltrain, US 101, I-280, and SR 92 - 15-minute drive from San Francisco International Airport

Walk to the Beach from this Ocean Front Home
Your beachfront escape awaits you. Come immerse yourself in the serenity of this Pacific Ocean retreat gracefully set in a secluded beach just 25 mins south of San Francisco. This 2 bed / 2 bath home features breathtaking ocean views and direct beach access just a few steps down. The hot tub overlooking the ocean, fire pits and a putting green complete this idyllic space. Comfortably sleeps 4 adults on 2 king beds and 2 high quality airbeds are provided for total sleeping for 6.

Extraordinary Ocean Views from Modern Abode
Tranquility awaits in our ocean view home. Enjoy beautiful ocean and mountain views from the living room, deck, kitchen and primary bedroom of this new, modern home. The beach is a brief 2-block walk away. Watch the surf and hear the soothing ocean waves from the deck and from the interior. Hardwood floors throughout the home are warm and inviting, enhanced by the maple quilted or birdseye veneer walls. A modern gas fireplace adds that extra touch of coziness.

Oceanfront w/ Direct Beach Access + New Hot Tub
This private oceanfront retreat offers direct beach access, lush gardens, and a spacious lawn. Walk to restaurants, music venues, and galleries nearby. Relax in the hot tub with ocean views or gather around the fire pit at sunset. Surfer’s Beach and Princeton Harbor are just north, and the Coastal Trail passes by for scenic biking and walking. Enjoy surfing, golfing, horseback riding, swimming—or simply unwind with a cocktail while watching the sunset.

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!

Luxury Silicon Valley Wellness and Work Oasis
Ideal for business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

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
Popular amenities for Hillsborough house rentals
House rentals with a pool

3 BR Home on Vineyard nr Palo Alto & Stanford

Private cul-de-sac home in Marin with pool

Views for Miles | Hot Tub | Gated Hilltop Home

Luxury 4-Suite Carbon-Neutral Home With Pool

Private Oasis with Pool and Fire Pit

Zen Meets Pool Retreat!

Little Poolside House near Downtown. New AC!

Large Home in Palo Alto, 5 bedrooms, Pool
Weekly house rentals

Incredible Ocean Views from Tuscan Villa Suite

The Perfectly Appointed Modern English Guest House

TreeTops OceanView Retreat_HotTub_Month/LongTermOk

Lagoonfront Retreat: 3BR House Near SFO

A private beachy pad in Montara

Luxury Ocean Front & Harbor View Home

Sea Wolf Bungalow

Fabulous Beach Get Away - Brand New Beach House
Private house rentals

Ocean Mountain View Home - Walk to Trails Beach

Poplar Beach Getaway: Family-Friendly, Near Beach!

New- Stunning Oceanfront "Pelican Bluffs"

★EV+★Hillside SFO View★Home Theater★Pool Table

Coastal Cottage

Oceanview Beach Home Walk to Beach Trails Food

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

Lagoon Living Offsite + Family Retreat!
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 959 | ﺩ.ﺇ 1,098 | ﺩ.ﺇ 1,039 | ﺩ.ﺇ 903 | ﺩ.ﺇ 973 | ﺩ.ﺇ 1,172 | ﺩ.ﺇ 918 | ﺩ.ﺇ 738 | ﺩ.ﺇ 731 | ﺩ.ﺇ 914 | ﺩ.ﺇ 914 | ﺩ.ﺇ 918 |
| 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 |
Destinations to explore
- San Francisco Vacation rentals
- San Jose Vacation rentals
- Mammoth Lakes Vacation rentals
- Santa Barbara Vacation rentals
- South Lake Tahoe Vacation rentals
- Oakland Vacation rentals
- Sacramento Vacation rentals
- Reno Vacation rentals
- Monterey Vacation rentals
- Santa Cruz Vacation rentals
- Fresno Vacation rentals
- Three Rivers Vacation rentals
- Stanford University
- Golden Gate Park
- Santa Cruz Beach
- Santa Cruz Beach Boardwalk
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
- Moscone Center
- University of California-Berkeley
- Levi's Stadium
- Henry Cowell Redwoods State Park
- Rio Del Mar Beach
- Pier 39
- Mission Dolores Park
- Six Flags Discovery Kingdom
- University of California San Francisco
- California’S Great America
- Seacliff State Beach
- Palace of Fine Arts
- Oakland Arena
- Rodeo Beach
- Big Basin Redwoods State Park
- Bernal Heights
- Baker Beach





