
House holiday rentals in Hillsborough
Find and book unique houses on Airbnb
Top-rated house rentals in Hillsborough
Guests agree: these houses are highly rated for location, cleanliness and more.

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!

Charming Retreat 2 BR Main House in SFO/Bay Area
Welcome to our inviting home With 3 comfortable queen size beds. The spacious living room boasts a comfortable sofa that can be folded down into a sofa bed, fully equipped kitchen adds flexibility to your dining options. Unbeatable location in a safe, pleasant neighborhood, Incredibly quiet despite being so close to the airport, 2 block to brand new SB Rec and Aquatic Center, minutes to downtown, restaurant, shopping, Freeway! High speed WiFi, Our Airbnb ensures easy access to key attractions

Modern House w A/C No Pet in San Mateo
This cozy home is kids friendly, good for a family vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles

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

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.

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
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 house rentals in Hillsborough
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Large Home in Palo Alto w/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

Beautiful 4 Bedroom Hillside Retreat

The Hacienda- Santa Cruz Mountain Ridgetop Retreat

Zen Meets Pool Retreat!
Weekly house rentals

Brighton Beach Cottage, One Bedroom plus Loft

Bright Spanish-style home in Burlingame

Charming Burlingame Beauty!

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

Oceanview Retreat, Steps to Beach|Pier|Golf Course

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

Upscale Modern House Near Mountain View Downtown

2 bedrooms house with sauna
Private house rentals

Stunning 3-Bedroom Mediterranean + Studio Unit

Chique 2-bedroom home near Stanford Hospitals

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

Super Private Hidden Redwood City House and Garden

Seaside Home Modern Retreat with Breathtaking

Spectacular California Ocean Front Home!

Lavish Modern Home 4BR near SFO/Palo Alto/Stanford

New- Stunning Oceanfront "Pelican Bluffs"
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 SGD | $287 SGD | $287 SGD | $258 SGD | $328 SGD | $328 SGD | $321 SGD | $258 SGD | $256 SGD | $208 SGD | $249 SGD | $257 SGD |
| 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Hillsborough holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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
- San Francisco Bay Area Holiday rentals
- San Francisco Holiday rentals
- Gold Country Holiday rentals
- Central California Holiday rentals
- San Francisco Peninsula Holiday rentals
- San Jose Holiday rentals
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- Santa Barbara Holiday rentals
- Wine Country Holiday rentals
- Oakland Holiday rentals
- Rentals with a patio Hillsborough
- Rentals with a washing machine and dryer Hillsborough
- Fitness-friendly rentals Hillsborough
- Flat rentals Hillsborough
- Rentals with a firepit Hillsborough
- Rentals with a hot tub Hillsborough
- Rentals with outdoor seating Hillsborough
- Family-friendly rentals Hillsborough
- Pet-friendly rentals Hillsborough
- Rentals with pools Hillsborough
- Rentals with a fireplace Hillsborough
- House rentals San Mateo County
- House rentals California
- House rentals United States
- Santa Cruz Beach
- Stanford University
- Golden Gate Park
- Capitola Beach
- Baker Beach
- Muir Woods National Monument
- Oracle Park
- Rio Del Mar Beach
- Golden Gate Bridge
- Seacliff State Beach
- Twin Peaks
- SAP Center
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Pier 39
- Montara Beach
- Bolinas Beach
- Palace of Fine Arts
- Six Flags Discovery Kingdom
- Davenport Beach
- Pescadero State Beach
- Twin Lakes State Beach
- Winchester Mystery House
- California’S Great America




