
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 2,490 verified reviews to help you choose

Family-friendly vacation rentals
40 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
60 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.

Fabulous Beach Get Away - Brand New Beach House
Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

Beach House ~180° Views, Hot Tub, Curated Interior
A blissful coastal retreat with unparalled ocean views, the Ocean Parkway House is nestled on a secluded bluff over looking the Pacific. This unique 1960's Bolinas beach house is a spot to truly relax and unwind. Fully updated with a curated mix of vintage and modern furnishings - our cottage has a mid-century design sensibility with luxuries like Coyuchi towels, a chef's kitchen, Scandinavian fireplace, outdoor rain shower, cedar hot tub, and new heated stone loveseat on the upstairs deck.

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.

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).

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.

A private beachy pad in Montara
Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

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!

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

Seaside Home Modern Retreat with Breathtaking
Discover coastal serenity in this modern 4BR, 3 bath retreat in Half Moon Bay's Miramar district. With clean interior, wood accents & an amazing 2nd-floor balcony, this home offers a serene escape. Enjoy the landscaped backyard, fully stocked kitchen & proximity to popular beaches and the Coastal Trail. Experience seaside charm in this unforgettable home
Popular amenities for Hillsborough house rentals
House rentals with a 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

Luxury Silicon Valley Wellness and Work Oasis

Private Oasis with Pool and Fire Pit

3 BR Home on Vineyard nr Palo Alto & Stanford

Beautiful 4 Bedroom Hillside Retreat
Weekly house rentals

10 min to SFO! Panoramic Bay-View+Hot Tub+Tesla

Canyon Oak House: Private, tranquil with trees

Mill Valley Gem: Modern cozy w/Patio/Tesla Charger

Spectacular California Ocean Front Home!

Poplar Beach Getaway - Special Pricing!

Bright Spanish-style home in Burlingame

Charming Burlingame Beauty!

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

Brand New Executive Home

Super Private Hidden Redwood City House and Garden

Miramar Penthouse Coastal Elegance in the Heart of

Business-Friendly 2/1. Walk to Caltrain/Downtown.

Modern 3BR/3.5BA House with Parking & Laundry

Panoramic Bay View 4BR • Single-Level · 1Gbps WiFi

Cozy Half Moon Bay with Mountain and Oceanview

Lavish Modern Home 4BR near SFO/Palo Alto/Stanford
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ735 | ﺩ.ﺇ819 | ﺩ.ﺇ819 | ﺩ.ﺇ738 | ﺩ.ﺇ936 | ﺩ.ﺇ936 | ﺩ.ﺇ918 | ﺩ.ﺇ738 | ﺩ.ﺇ731 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ918 |
| 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
- Northern California Vacation rentals
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- Apartment rentals Hillsborough
- Rentals with a fire pit Hillsborough
- Rentals with a hot tub Hillsborough
- Rentals with a washer and dryer Hillsborough
- Pet-friendly rentals Hillsborough
- Family-friendly rentals Hillsborough
- Rentals with outdoor seating Hillsborough
- Rentals with a fireplace Hillsborough
- Rentals with a patio Hillsborough
- Fitness-friendly rentals Hillsborough
- Rentals with pools Hillsborough
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- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
- Rio Del Mar Beach
- SAP Center
- Santa Cruz Beach Boardwalk
- Pier 39
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Seacliff State Beach
- Twin Peaks
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Rodeo Beach
- Palace of Fine Arts
- Levi's Stadium
- Montara Beach
- Winchester Mystery House
- Bolinas Beach




