
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.

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.

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.

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.

Oceanfront Oasis, Sunsets & Crashing Waves
The Bluffs Oceanfront Oasis awaits you. Our beautifully appointed home sits right on the cliff boasting crashing waves and endless sunsets. Start your day in the zen room for a bit of yoga and meditation or take a leisurely walk on the beach trail right out the back gate. After dining out or in, end your evening with something special while seated at the firepit over looking the Pacific. Come for a romantic getaway, a weekend of golf or a family fun filled vacation.

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.

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!

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.

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

3BR Eichler home w/ backyard & BBQ grill
Welcome to a classic Eichler home in San Mateo - thoughtfully renovated, full of character, and perfectly placed for Bay Area access. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural & red maple tree - Private backyard w/ fire pit, BBQ & 8-person dining area - Dedicated office w/ door & fast Wi-Fi - ideal for remote work - 20 mins to SF | 15 mins to SFO | near Caltrain
Popular amenities for Hillsborough house rentals
House rentals with a pool

Lafayette Treehouse - Relax and Rejuvenate

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 Silicon Valley Wellness and Work Oasis

Little Poolside House near Downtown. New AC!

Private Oasis with Pool and Fire Pit

Luxury 4-Suite Carbon-Neutral Home With Pool
Weekly house rentals

Incredible Ocean Views from Tuscan Villa Suite

The Perfectly Appointed Modern English Guest House

TreeTops OceanView Retreat_HotTub_Month/LongTermOk

A private beachy pad in Montara

Fabulous Beach Get Away - Brand New Beach House

Ocean Mountain View Home - Walk to Trails Beach

Ocean Beach Lux Retreat Back from Remodel

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard
Private house rentals

Walk to Beach - Remodeled Coastal Home Safe Town

Ocean View House Few Steps from Miramar Beach

Relaxing Backyard Retreat -Spacious + Bright Home

SF Amazing View & SUNroom: Spacious Private 1 bdrm

Tranquil Coastal Retreat - Walk to the Beach!

Cabo San Pedro - penthouse - Stunning Ocean Views

Newly remodeled hilltop home with stunning views

Mill Valley secluded Artist's Retreat
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,582 GYD | G$62,529 GYD | G$59,183 GYD | G$42,034 GYD | G$53,327 GYD | G$53,327 GYD | G$52,281 GYD | G$42,034 GYD | G$41,616 GYD | G$52,072 GYD | G$52,072 GYD | G$52,281 GYD |
| 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
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- Rentals with a fire pit Hillsborough
- Rentals with a hot tub Hillsborough
- Apartment rentals Hillsborough
- Rentals with a fireplace Hillsborough
- Family-friendly rentals Hillsborough
- Rentals with a patio Hillsborough
- Rentals with a washer and dryer Hillsborough
- Fitness-friendly rentals Hillsborough
- Rentals with pools Hillsborough
- Pet-friendly rentals Hillsborough
- Rentals with outdoor seating Hillsborough
- House rentals San Mateo County
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- House rentals United States
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Muir Woods National Monument
- Santa Cruz Beach Boardwalk
- Golden Gate Bridge
- Capitola Beach
- Oracle Park
- Moscone Center
- University of California-Berkeley
- SAP Center
- Levi's Stadium
- Henry Cowell Redwoods State Park
- Pier 39
- Rio Del Mar Beach
- Mission Dolores Park
- Six Flags Discovery Kingdom
- Chase Center
- University of California San Francisco
- California’S Great America
- Seacliff State Beach
- Palace of Fine Arts
- Rodeo Beach
- Montara Beach





