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House vacation rentals in Hillsborough

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Top-rated house rentals in Hillsborough

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Home in Half Moon Bay

4.85 out of 5 average rating, 289 reviews

* Beachfront Paradise * with Direct Beach Access

This private and magical property has direct beach access! The grounds are gorgeous with lush gardens and an expansive lawn. It's walking distance to restaurants, music venues & galleries. Enjoy ocean views while you relax in the hot tub or snuggle by the fire pit! Surfer's Beach + Princeton Harbor are just to the north. The Coastal Trail passes by and is perfect for biking or walking. Enjoy surfing, golfing, horse back riding, swimming or just relaxing with a cocktail while watching the sunset!

Home in Half Moon Bay

4.89 out of 5 average rating, 322 reviews

Poplar Beach Getaway - Special Pricing!

Family-friendly, relaxed home located in a quiet residential neighborhood awaits you for your beach getaway. A 10-minute walk to lovely Poplar Beach and 1/2 mile from scenic Main Street restaurants, shops and cafes. Three bedrooms with queen beds, two baths, living area, well-equipped kitchen, spacious kid-friendly den and backyard with deck ensure that you have room to spread out and relax after a fun day at the beach or exploring the area. Short drive to San Francisco, Santa Cruz or San Jose.

Home in Half Moon Bay

4.99 out of 5 average rating, 311 reviews

Stairway to Heaven - 1 bedroom

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. PLEASE NOTE, the home next to us is doing a renovation, there may be noise on weekdays.

Home in San Mateo

4.91 out of 5 average rating, 148 reviews

Andulore Cottage - Near Burlingame Ave - Remodeled

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.

Home in Muir Beach

4.93 out of 5 average rating, 336 reviews

Ocean Front Beach Cottage with Hot Tub & Fireplace

Small cottage right on the beach. Very close to San Francisco - 20 min from the Golden Gate Bridge. Romantic getaway. Perfect for couples or as a quiet retreat for an individual. Wood-burning fireplaces in the living room and bedroom. Large deck and private hot tub overlooking the ocean. Feel free to ask me any specific questions you may have and I'll make sure to get back to you promptly. Please consider signing up for travel insurance in case you have a change of plans or get sick.

Home in Burlingame

4.97 out of 5 average rating, 156 reviews

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.

Home in Livermore

4.98 out of 5 average rating, 220 reviews

The French Door

This space is a private entry 275 square foot small studio with a private bath, connected to the main house but with no access to the main house. The unit has a standard sized mini fridge, microwave and keurig coffee maker with coffees to choose from, a very mini toaster oven for one bagel or one piece of toast, lite snacks and waters for you. Also a small table and chair set, small desk and a full size bed. The location is wonderful if you work at the lab or want to go wine tasting!

Home in Burlingame

4.92 out of 5 average rating, 169 reviews

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

Home in Belmont

4.92 out of 5 average rating, 355 reviews

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

Home in San Mateo

4.83 out of 5 average rating, 272 reviews

❤️ Delightful 1B/1B modern with a leisure garden

It has recently been upgraded with a master bedroom featuring a full bathroom and two closets, as well as a large living space. Complete privacy is ensured with a separate fence, and the unit includes a sunny private garden. We offer free coffee and tea, and there's 24/7 free street parking. Walking distance to the Roblox office and San Mateo Event Center. Approximately 10 minutes from SFO. BTW. This is not an apartment building. Check yourself in with the key code.

Home in Montara

4.98 out of 5 average rating, 308 reviews

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.

Home in San Mateo

4.9 out of 5 average rating, 229 reviews

Serene Modern Home w/Private Yard

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!

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Popular amenities for Hillsborough house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in San Mateo

4.8 out of 5 average rating, 15 reviews

Charming English Oasis

Home in Willow Glen

4.81 out of 5 average rating, 194 reviews

Beautiful Large 4BR Home with POOL

Home in Concord

4.92 out of 5 average rating, 195 reviews

Pool, Hot tub, Napa, SFO Clean

Home in Newark

4.93 out of 5 average rating, 120 reviews

Modern Cozy Oasis | Silicon Valley | Private Pool

Home in Los Altos Hills

4.96 out of 5 average rating, 70 reviews

Beautiful home Pool/spa 4bd/4ba Los Altos Hills

Home in Mountain View

4.91 out of 5 average rating, 138 reviews

Little Poolside House near Downtown Mountain View!

Home in San Jose

4.86 out of 5 average rating, 125 reviews

Beautiful 3BD Home w/ Heated Pool and Fire Pit

Home in San Rafael

4.91 out of 5 average rating, 492 reviews

MCM Waterfront Pool/Hot Tub between SF and Napa

Weekly house rentals

Home in Pacifica

4.99 out of 5 average rating, 291 reviews

Oceanfront Boho Retreat - Pacific Sunset Views 🌅🌊🐳

Home in Stinson Beach

4.99 out of 5 average rating, 121 reviews

Remodeled Stinson Seadrift Lagoon Escape

Home in Pescadero

4.91 out of 5 average rating, 159 reviews

Oceanfront Views - Steps to the Beach

Home in Pacifica

4.82 out of 5 average rating, 131 reviews

Jacuzzi Pool Table Sauna Resort Style Home 5 Stars

Home in Pacifica

4.94 out of 5 average rating, 109 reviews

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard

Home in Half Moon Bay

4.91 out of 5 average rating, 109 reviews

2 bedrooms house with cedar hot tub or sauna

Home in Montara

4.94 out of 5 average rating, 112 reviews

Ocean view house, beaches, trails, family friendly

Home in Pedro Point-Shelter Cove

4.93 out of 5 average rating, 488 reviews

Artist's ocean view retreat

Private house rentals

Home in Pacifica

4.96 out of 5 average rating, 204 reviews

Brighton Beach Cottage, One Bedroom plus Loft

Home in Burlingame

4.97 out of 5 average rating, 34 reviews

Bright Spanish-style home in Burlingame

Home in Half Moon Bay

4.98 out of 5 average rating, 130 reviews

Beautiful Seaside Retreat.

Home in Burlingame

5 out of 5 average rating, 43 reviews

Charming Burlingame Beauty!

Home in Montara

5 out of 5 average rating, 84 reviews

Sea Wolf Bungalow

Home in San Mateo

5 out of 5 average rating, 7 reviews

Home Oasis walkable to downtown

Home in Foster City

5 out of 5 average rating, 41 reviews

Resort Style, Modern Home 3BR near SFO, Stanford

Home in San Mateo

4.87 out of 5 average rating, 241 reviews

Modern House w A/C No Pet in San Mateo

Quick stats about house rentals in Hillsborough

Total rentals
80 properties
Total number of reviews
3.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Destinations to explore