House vacation rentals in Hillsborough

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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.

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Top guest favorite
A modern living area features a sectional sofa complemented by a glass coffee table. Large sliding doors provide natural light and a view of the outdoor space. A sleek fireplace adds warmth to the room, with a stylish area rug enhancing the comfortable setting.
Home in Miramar
5 out of 5 average rating, 142 reviews

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.

Top guest favorite
A wooden deck features two lounge chairs facing the ocean, providing unobstructed views of the sun setting over the Pacific. The surrounding native garden enhances the tranquil atmosphere, while rolling coastal bluffs can be seen in the background.
Home in Bolinas
4.99 out of 5 average rating, 129 reviews

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.

Top guest favorite
A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.
Home in Half Moon Bay
4.96 out of 5 average rating, 172 reviews

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.

Top guest favorite
A stylish living room features a modern red chair alongside a patterned gray-and-white armchair. A wooden coffee table sits on a plush area rug, with a television mounted above a classic fireplace. Decorative elements are arranged on the mantel, adding a touch of sophistication.
Home in San Mateo
4.92 out of 5 average rating, 189 reviews

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.

Top guest favorite
An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.
Home in Mill Valley
4.99 out of 5 average rating, 120 reviews

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.

Guest favorite
The exterior of a multi-level home features a blend of large windows and a distinctive round window. The light-colored facade is complemented by lush greenery and flowering plants in the foreground. A spacious front deck is visible, enhancing the inviting appearance of the property.
Home in Burlingame
4.96 out of 5 average rating, 180 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.

Top guest favorite
The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.
Home in San Carlos
4.96 out of 5 average rating, 303 reviews

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).

Top guest favorite
A vibrant sunset sky displays shades of purple and orange, casting a warm glow over the ocean waves below. Silhouetted trees frame the view, adding depth to the picturesque coastal landscape with distant mountains visible under the evening light.
Home in Montara
4.98 out of 5 average rating, 122 reviews

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.

Top guest favorite
The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.
Home in Montara
4.98 out of 5 average rating, 398 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.

Top guest favorite
A spacious living room features large windows allowing for ample natural light. Comfortable seating is arranged with a gray sofa and dark armchairs. A glass coffee table sits atop a plush area rug, while artwork adorns the walls, adding a touch of color to the neutral palette.
Home in San Mateo
4.92 out of 5 average rating, 299 reviews

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!

Top guest favorite
Home in San Mateo
4.88 out of 5 average rating, 132 reviews

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

Top guest favorite
The living room features a light-filled space with large windows on either side, framed by minimalist decor. A modern fireplace serves as a focal point, complemented by a surfboard mounted above. Comfortable seating is arranged around a neutral-toned coffee table on a textured area rug.
Home in Miramar
4.96 out of 5 average rating, 103 reviews

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

When is the best time to visit Hillsborough?

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