
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.

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.

The Perfectly Appointed Modern English Guest House
Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain).

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.

Canyon Oak House: Private, tranquil with trees
Looking for a serene getaway in San Carlos/mid peninsula? Tranquil, professionally cleaned retreat with lots of breathing space perched among the trees in Devonshire Canyon, San Carlos, CA. Enjoy evening sun on the large deck, wake up to the birds in the trees or a family of deer in the garden. Conveniently close to downtown San Carlos but feels like you're in the country. FAST WIFI. CLOSE TO 280 AND 101. We will consider pets (additional cleaning fee applies).

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 Home in Pacifica
Experience the ultimate coastal living with the Pacific Ocean as your backyard on Pedro Point—recently featured on the television series Staycation NorCal: A Golden Baycation. Boasting breathtaking, unobstructed ocean views, this stunning 3 BR 2-bath home offers a serene retreat. Walk to the surf and beach just steps from home. Enjoy sunsets from the deck, cozy nights by the gas fire pit, and catch the Golden Gate Bridge on a clear horizon.

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

Beautiful 4 Bedroom Hillside Retreat

Views for Miles | Hot Tub | Gated Hilltop Home

Luxury Silicon Valley Wellness and Work Oasis

Little Poolside House near Downtown. New AC!

Luxury 4-Suite Carbon-Neutral Home With Pool

Private Oasis with Pool and Fire Pit
Weekly house rentals

Oceanfront w/ Direct Beach Access + New Hot Tub

Luxury Ocean Front & Harbor View Home

Incredible Ocean Views from Tuscan Villa Suite

2 bedroom house with hot tub

Ocean Mountain View Home - Walk to Trails Beach

A private beachy pad in Montara

Fabulous Beach Get Away - Brand New Beach House

TreeTops OceanView Retreat_HotTub_Month/LongTermOk
Private house rentals

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

SF Amazing View & SUNroom: Spacious Private 1 bdrm

Tranquil Coastal Retreat - Walk to the Beach!

Newly remodeled hilltop home with stunning views

Cabo San Pedro - penthouse - Stunning Ocean Views

Relaxing Backyard Retreat -Spacious + Bright Home

Beach House ~180° Views, Hot Tub, Curated Interior

Sea Barn•Family Beach Home•Surf•Bike•Trampoline
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,531 GYD | G$62,470 GYD | G$59,128 GYD | G$41,995 GYD | G$53,277 GYD | G$53,277 GYD | G$52,233 GYD | G$41,995 GYD | G$41,577 GYD | G$52,024 GYD | G$52,024 GYD | G$52,233 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 pools Hillsborough
- Pet-friendly rentals Hillsborough
- Rentals with a washer and dryer Hillsborough
- Fitness-friendly rentals Hillsborough
- Rentals with outdoor seating Hillsborough
- House rentals San Mateo County
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- 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





