
House holiday rentals in Hillsborough
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Top-rated house rentals in Hillsborough
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SF Amazing View & SUNroom: Spacious Private 1 bdrm
👋 Welcome to our spacious, clean, private getaway studio on Southern Hill in Daly City. Escape the hustle and bustle of the city. Enjoy a stunning view of day/night in clear days ☀️ - Easy street parking - Great Summit Loop Trail at San Bruno Mountain (6-min🚘) - Cow Palace Arena (8-min🚘) - H Mart grocery mall (10-min🚘) - 9.2 miles to SFO (17-min🚘) - 6.7 miles to Civic Center(>30-min🚘 w/ traffic or 20-min🚘 w/o traffic) - 11 miles to Fisherman's Wharf(>35-min🚘 w/ traffic or 23-min🚘 w/o traffic)

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat
Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

❤️ Delightful 1B/1B modern with a leisure garden
This recently upgraded unit features a master bedroom with a full bathroom and two closets, along with a spacious living area. Enjoy complete privacy with a separate fence and a sunny private garden. We provide complimentary coffee and tea, and there’s free street parking available 24/7. It’s within walking distance to the Roblox office and the San Mateo Event Center, and about 10 minutes from SFO. Please note, this is not an apartment or condo building. Self check-in o& Check out with code.

Stairway to Heaven - 1 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 2 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.

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.

Hidden French Gem for Fam/Biz~near Caltrain,SFO
Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

Stylish & Serene Home - Private Unit!
Discover our chic and contemporary 1-bed, 1-bath house in South San Francisco! Recently renovated, it offers a comfortable queen-size bed for a restful stay. Relax with the 55" TV (HBO Max) after exploring, and enjoy your own kitchen for home-cooked meals or our top restaurant recommendations. Conveniently near SFO / transportation hubs and not far from the city, this is your ideal base to explore the Bay Area. We look forward to hosting your comfortable and convenient stay!

12-Min From SFO, Tastefully Designed, Work Station
Welcome to the Laurel Pad, a home away from home. You'll enjoy the convenience this house offers - fully stocked kitchen, minutes away from amazing restaurants, supermarkets, parks, 13-min to SFO, 25-min to downtown San Francisco, and easy access to major companies around Silicon Valley. This bright and sunny house is tastefully designed and updated to offer functionality and aesthetics. You'll have access to fast wifi and dedicated driveway parking for up to two cars.

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).

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!
Popular amenities for Hillsborough house rentals
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Beautiful Large 4BR Home with POOL

Large Home in Palo Alto, close to Levi's Stadium

Little Poolside House near Downtown Mountain View!

Waterfront home w/ private dock and pool

Chic & Fun Mid-Century Modern sleeps 8 (pool)

Lafayette Treehouse - Relax and Rejuvenate

3 BR Home on Vineyard nr Palo Alto & Stanford
Weekly house rentals

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

Walk to Beach - Remodeled Coastal Home Safe Town

Canyon Oak House: Private, tranquil with trees

Scenic Retreat with A/C, Gem Close to SFO/SF/Beach

Serene Bayview Single-Level 4BR Retreat

Brighton Beach Cottage, One Bedroom plus Loft

Bright Spanish-style home in Burlingame

Stafford Place
Private house rentals

Miramar Penthouse Coastal Elegance in the Heart of

Super Private Hidden Redwood City House and Garden

Seaside Home Modern Retreat with Breathtaking

Executive Home w/ Sun Deck

Newly renovated 2bed/1bath home

Charming Burlingame Beauty!

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

Seaside Art Gallery Loft Inspire Your Creativity
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $333 NZD | $371 NZD | $371 NZD | $334 NZD | $424 NZD | $424 NZD | $416 NZD | $334 NZD | $331 NZD | $414 NZD | $414 NZD | $416 NZD |
| 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, Wi-Fi 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
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- Wine Country Holiday rentals
- South Lake Tahoe Holiday rentals
- Rentals with a patio Hillsborough
- Family-friendly rentals Hillsborough
- Rentals with a fireplace Hillsborough
- Rentals with outdoor seating Hillsborough
- Pet-friendly rentals Hillsborough
- Apartment rentals Hillsborough
- Rentals with a washing machine and dryer Hillsborough
- Fitness-friendly rentals Hillsborough
- Rentals with pools Hillsborough
- Rentals with a fire pit Hillsborough
- Rentals with a hot tub Hillsborough
- House rentals San Mateo County
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- House rentals United States
- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Levi's Stadium
- Capitola Beach
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
- Rio Del Mar Beach
- Seacliff State Beach
- Baker Beach
- Twin Peaks
- SAP Center
- Santa Cruz Beach Boardwalk
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Pier 39
- Las Palmas Park
- University of California-Berkeley
- Montara Beach
- Six Flags Discovery Kingdom
- Palace of Fine Arts
- Bolinas Beach




