
House holiday rentals in Hillsborough
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Top-rated house rentals in Hillsborough
Guests agree: These houses are highly rated for location, cleanliness and more.

Serene Oasis in the midst of Silicon Valley
Gaze out at the beautiful green canyon while having a morning coffee in bed. Head to the fully equipped kitchen to prepare breakfast and enjoy it outside on the balcony, surrounded by the sights and sounds of this stunning hilltop location. Close to 280. Centrally located in Silicon Valley for easy access to both San Jose and San Francisco. Deck/BBQ Lounge Area. Minimal. Enjoy life in the San Carlos hills. Drive about 5 minutes to lively San Carlos downtown for several restaurants and bars. Go hiking in Edgewood, Crestview, or Big Canyon. For a taste of big city life, adventure a bit further to San Francisco. Driving is the best option, I280 and 101 are easily accessible. Cal Train station down the hill - connects all the way from San Francisco to San Jose. Very spacious unit ( approximately 1200 sq.ft )

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!

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!

Walk to Burlingame Dining & Shops - Near SFO - A/C
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.

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

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.

Cozy San Mateo home / Near SFO Airport
Looking for the perfect short-term rental in the Bay Area? This fully furnished 3-bed, 2-bath home in San Mateo is ideal for families, business travelers, and vacationers. Located just six blocks from vibrant downtown, you’ll be steps from ethnic restaurants, boutique shopping, and local charm. Just 10 minutes from SFO airport. Easy access to San Francisco and San Jose. This inviting home is your ideal base for experiencing the best of the Peninsula.

Lagoonfront Retreat: 3BR House Near SFO
Our stunning Airbnb listing offers both convenience and relaxation. 5min to multiple supermarkets and 15mins to SFO. Enjoy breathtaking views of the lagoon, modern decor, a fully-equipped kitchen, two comfortable living areas, and three cozy bedrooms with high-quality linens. We provide high-speed Wi-Fi, working desks, and heating for your comfort. We look forward to hosting you and helping you make the most of your stay in this beautiful area.

Oceanfront Home in Pacifica, CA
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.
Popular amenities for Hillsborough house rentals
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Pool, Hot tub, Napa, SFO Clean

Large Home in Palo Alto w/Pool

Little Poolside House near Downtown Mountain View!

Waterfront home w/ private dock and pool

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

MCM Waterfront Pool/Hot Tub between SF and Napa

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

Oceanfront Boho Retreat - Pacific Sunset Views 🌅🌊🐳

Canyon Oak House: Private, tranquil with trees

12-Min From SFO, Tastefully Designed, Work Station

Poplar Beach Getaway - Special Pricing!

Bright Spanish-style home in Burlingame

Sunlit 2B1B house w/ Deck & Garden on Belmont hill

Charming Burlingame Beauty!

Oceanview Retreat, Steps to Beach|Pier|Golf Course
Private house rentals

Hot Tub Overlooking Pacific!

Super Private Hidden Redwood City House and Garden

Seaside Home Modern Retreat with Breathtaking

Modern 3BR/3.5BA House with Parking & Laundry

Spectacular California Ocean Front Home!

New- Stunning Oceanfront "Pelican Bluffs"

Spacious, Remodeled 2BR Duplex Unit by Downtown SM

Resort Style, Modern Home 3BR near SFO, Stanford
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $353 NZD | $394 NZD | $394 NZD | $355 NZD | $451 NZD | $451 NZD | $442 NZD | $355 NZD | $352 NZD | $286 NZD | $343 NZD | $353 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 3,070 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

4.8 Average rating
Hillsborough stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Northern California Holiday rentals
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- Apartment rentals Hillsborough
- Rentals with a fireplace Hillsborough
- Family-friendly rentals Hillsborough
- Rentals with pools Hillsborough
- Rentals with a patio Hillsborough
- Pet-friendly rentals Hillsborough
- Rentals with a fire pit Hillsborough
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- House rentals San Mateo County
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- Santa Cruz Beach
- Capitola Beach
- Stanford University
- Golden Gate Park
- Rio Del Mar Beach
- Oracle Park
- Muir Woods National Monument
- Seacliff State Beach
- Golden Gate Bridge
- California’S Great America
- Alcatraz Island
- Baker Beach
- Twin Peaks
- SAP Center
- Mission Dolores Park
- Montara State Beach
- Henry Cowell Redwoods State Park
- Bolinas Beach
- Pier 39
- Six Flags Discovery Kingdom
- Palace of Fine Arts'`
- Davenport Beach
- Twin Lakes State Beach
- Pescadero State Beach




