Pet-friendly holiday rentals in Hillsborough

4.87 out of 5 average rating, 1065 reviews

The sleeping area is adorned with warm wood finishes, featuring a spacious bed with soft linens. Natural light filters in through circular porthole windows, enhancing the classic nautical ambiance. A wooden dresser is positioned nearby, and a doorway leads to the bathroom, which is tastefully designed.

Boat in Alameda

Step back in time on this beautiful classic yacht

Good Luck is a hundred-year-old classic yacht, lovingly restored and ready to transport you to another time while luxuriously spoiling you on your bay area adventure. This dockside charter gives you complete privacy and an amazing nautical experience. Alameda is a beautiful island community in the heart of the Bay, filled with beautiful homes, adorable shops, and many great restaurants. The San Francisco ferry is close by to whisk you to the big city, so why would you want to stay anywhere else?

4.9 out of 5 average rating, 213 reviews

A private fenced backyard features comfortable seating, including a sectional sofa and coffee table. Soft lighting from cafe lights enhances the outdoor environment. Lush greenery surrounds the space, providing a natural backdrop, with a welcoming mat positioned at the entry.

Home in Pacifica

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!

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.

4.96 out of 5 average rating, 192 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.

4.92 out of 5 average rating, 109 reviews

Cabin in Boulder Creek

Either Way Hideaway

Relax and enjoy riverside views in our tranquil Santa Cruz Mountains guesthouse. Cozy by our fire pits, take a dip in a private hot tub and enjoy the sounds of the river flow by. Hike Big Basin, Castle Rock and Henry Cowell State Parks. Close to historic downtown Boulder Creek and the Santa Cruz boardwalk, it’s the perfect base for exploring Santa Cruz county. Immerse yourself in of nature while staying connected and comfortable. Either way, you’ll enjoy your stay! SCC Permit #251382

4.99 out of 5 average rating, 135 reviews

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

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.

4.94 out of 5 average rating, 103 reviews

The living area features a leather sofa paired with a patterned rug and a glass coffee table. A dining area is visible in the background, illuminated by natural light from large windows. Soft decorative elements, including a fluffy pouf and indoor plants, enhance the welcoming ambiance.

Home in Belmont

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

Escape to this peaceful retreat with new furniture, beautiful garden and nice views over Belmont hill! Luxury like your own home: - Leather sofa & Smart TV - Complete cookware and dining essentials - Big deck with a dining set - Large Private Backyard for relaxation Convenience: - Surrounded by various attractions - San Francisco and San Jose are both half-an-hour away - Easy access to Caltrain, US 101, I-280, and SR 92 - 15-minute drive from San Francisco International Airport

Guest suite in Half Moon Bay

A cozy outdoor seating area features two rattan chairs positioned on a deck. A small table rests between them, with a scenic ocean view visible in the background. Sunrise colors illuminate the sky, and a vibrant pink flamingo adds a playful touch to the greenery.

4.96 out of 5 average rating, 413 reviews

Oceanview Penthouse, Stylish, Walking to Beach

A perfect romantic getaways to this stylish indoor/outdoor Penthouse! We are 10 mins walk to beaches and 15 mins walk to award winning restaurants. There are a lot of fun activities: spending your days on the beach, exploring the hiking, biking, golfing, surfing, kayaking, paddle boarding or just simply kick back relax in this quiet and picturesque property with a panoramic ocean view, enjoying the sunset and the beautiful garden. We are 30 mins to SF or 60 mins to Santa Cruz.

4.95 out of 5 average rating, 151 reviews

A sunlit dining area is framed by large windows that provide a clear view of the ocean and sunset. A small round table is set with two black chairs, and a woven basket sits at the center, while a soft rug covers the floor.

Home in Moss Beach

Oceanfront Oasis, Sunsets & Crashing Waves

The Bluffs Oceanfront Oasis awaits you. Our beautifully appointed home sits right on the cliff boasting crashing waves and endless sunsets. Start your day in the zen room for a bit of yoga and meditation or take a leisurely walk on the beach trail right out the back gate. After dining out or in, end your evening with something special while seated at the firepit over looking the Pacific. Come for a romantic getaway, a weekend of golf or a family fun filled vacation.

4.98 out of 5 average rating, 258 reviews

The exterior of the cottage features a stone-accented porch with a wooden chair, framed by lush greenery and flowering plants. A pathway of stones leads from the well-kept lawn to the entry, where large double doors invite guests inside.

Cottage in San Carlos

Carmelita Creek House

The creek house is on a beautiful tree lined street, walking distance to downtown San Carlos. The house is a spacious one bedroom cottage with designer finishes and vaulted ceilings. You will be surrounded by mature redwoods and nature overlooking a year round creek. Amenities include a full sized kitchen, workspace, washer/dryer, fast WiFi, cable TV and a gas fireplace. Please note the cottage is located behind our main home and is accessed via several steps.

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.

4.95 out of 5 average rating, 119 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

4.87 out of 5 average rating, 119 reviews

Home in Montara

Oceanview Beach Home Walk to Beach Trails Food

Situated next to the stunning Montara State Beach and Montara Golden Gate National Recreation Area. Experience world class hiking, biking, beaches, restaurants, surfing, sunsets, family activities, and so much more. this location is a blend of natural beauty and recreational opportunities.. Easily access Bay Area's finest attractions .

Camper van/Motorhome in Half Moon Bay

An Airstream is positioned on a gravel area overlooking the Pacific Ocean. In the outdoor living space, a fire pit with four surrounding chairs is visible, along with a dining table that accommodates six. Lush green grass leads to the cliff edge, providing scenic coastal views.

4.95 out of 5 average rating, 298 reviews

Stunning California Coast Airstream (New Listing)

One of a kind Airstream overlooking a stunning beach, Pacific Ocean and California Coastline, perched high on a cliff to create an unforgettable magical experience of a lifetime. If you can’t find availability for the date you are interested, check out our second newer unit here https://www.airbnb.com/h/luxurycaliforniacoastairstream

Popular amenities for Hillsborough pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A welcoming living room features high ceilings and large windows allowing natural light to fill the space. A comfortable sofa with blue and yellow pillows faces a wooden coffee table, while decorative armchairs and a flat-screen TV complete the inviting atmosphere.

4.99 out of 5 average rating, 411 reviews

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

4.97 out of 5 average rating, 280 reviews

A spacious living room features a vaulted wood ceiling and large windows allowing natural light to fill the space. Comfortable seating includes a gray sofa and two armchairs. A central wooden table is placed on a decorative rug. Green curtains add a touch of color and style.

Home in San Rafael

Marin Retreat: Quiet Views Near SF & Muir Woods

Home in South San Francisco

The dining area features a large, rectangular table surrounded by four upholstered chairs, providing a comfortable setting. Natural light floods in through large windows, showcasing a view of the landscape. A decorative wall clock and a framed artwork add character to the space.

4.94 out of 5 average rating, 356 reviews

★EV+★Hillside SFO View★Home Theater★Pool Table

4.92 out of 5 average rating, 314 reviews

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

Serene Modern Home with Yard & Parking

4.93 out of 5 average rating, 214 reviews

A seating area is filled with natural light from large windows, showcasing a sunset over the ocean. Two plush chairs are positioned around a circular coffee table, while a telescope invites exploration of the coastal views. Greenery can be seen in the background.

Home in Moss Beach

Relaxing Getaway with Breathtaking Ocean Views

4.93 out of 5 average rating, 138 reviews

The game room features multiple vintage arcade machines, glowing under vibrant LED lighting. Various games line the walls, accompanied by bar-style seating. The energetic atmosphere is enhanced by a colorful mural surrounding the area, creating an immersive gaming experience.

Home in Pacifica

Massive Themed 5BD Game Room/Hot Tub/Pool Table

4.92 out of 5 average rating, 109 reviews

A living area is highlighted by a spacious sofa adorned with red and white cushions. A wooden coffee table sits in front, surrounded by a patterned area rug. A large wall-mounted television is positioned above a fireplace, with natural light flowing through the nearby window.

Home in Redwood City

Delightful Stay

A hot tub is situated on a brick surface, surrounded by neatly trimmed bushes. In the background, a palm tree is visible, along with distant hills and power lines. The sky displays soft morning light, hinting at an ocean view beyond the greenery.

4.85 out of 5 average rating, 304 reviews

Studio: Hot Tub + ocean view

Pet-friendly home rentals with a pool

Guest house in San Rafael

A large saltwater pool glistens under a clear blue sky, surrounded by lush greenery. The view overlooks the hills and twinkling lights of San Rafael, providing a serene backdrop for relaxation.

4.98 out of 5 average rating, 246 reviews

Hillside Wellness Retreat | Pool, Gym & A/C

Guest house in Walnut Creek

An open-concept living space is highlighted by a modern kitchen featuring light cabinetry and stainless steel appliances. Large windows provide natural light and scenic views. A cozy seating area includes a dark sectional sofa facing a television, and a colorful area rug adds warmth to the floor.

4.94 out of 5 average rating, 141 reviews

The Willow Cottage

4.93 out of 5 average rating, 178 reviews

An aerial view captures the expansive outdoor area of the Anton Menlo Apartments. A resort-style pool is centrally located, surrounded by lounge chairs and shaded seating areas. Lush landscaping and modern architecture define the space, with additional amenities visible, including a community lounge.

Flat in Menlo Park

Beautiful Spacious Living w/Resort Like Feel

4.95 out of 5 average rating, 109 reviews

A clear blue pool is surrounded by a stone deck, featuring two wooden lounge chairs positioned for relaxation. Lush greenery and palm trees frame the area, providing a natural and serene setting in the private backyard.

Home in San Rafael

Private cul-de-sac home in Marin with pool

4.94 out of 5 average rating, 159 reviews

A modern living area features a comfortable blue leather sofa and a light, textured armchair. A wooden coffee table with decorative items is centered on a patterned rug. Large sliding glass doors provide a view of the sunset and access to the outdoor space.

Home in East San Jose

Views for Miles | Hot Tub | Gated Hilltop Home

4.96 out of 5 average rating, 197 reviews

A serene outdoor space showcases a clear lap pool surrounded by lush greenery and palm trees. A shaded seating area under a canopy is visible, along with vibrant plants reflecting in the water, creating an inviting atmosphere for relaxation.

Guest suite in Sunnyvale

Tranquil Garden Retreat • Poolside Serenity

Guest house in San Rafael

A full moon illuminates the night sky over the bay, casting a soft glow on the water below. The view captures the city lights and distant mountains, along with the silhouette of a bridge spanning the bay, creating a serene nighttime landscape.

4.87 out of 5 average rating, 193 reviews

Farm in the city & sweeping bayview

4.88 out of 5 average rating, 116 reviews

A well-maintained pool area is surrounded by lush grassy space and tall palm trees. Two lounge chairs are positioned beside the sparkling blue pool, while potted plants add greenery to the setting. A wooden fence encloses the area, providing privacy.

Home in Concord

Craftman’s Castle

Private, pet-friendly home rentals

4.97 out of 5 average rating, 151 reviews

A secluded outdoor area features a hot tub surrounded by lush greenery. A shaded patio sits nearby with white lounge chairs, while a portion of the building is visible in the background, incorporating large windows and a deck area adorned with outdoor furnishings.

Farm stay in Woodside

Apartment w hot tub / forest & ocean view

4.97 out of 5 average rating, 376 reviews

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

Guest house in Woodside

SkyHigh Redwoods Retreat with Bay Views

4.94 out of 5 average rating, 162 reviews

Natural light fills the spacious living area, which features a comfortable couch and a round coffee table. Double glass doors lead to a serene patio adorned with greenery, while a dining area with wooden chairs sits opposite a well-equipped kitchen.

Cottage in Redwood City

Adorable Garden Cottage near Stanford

Guest house in Redwood City

A shaded porch area features stone flooring and is bordered by lush greenery. Two outdoor chairs and a small table are positioned on the left side, providing a serene spot for relaxation. The entrance to the studio is visible through large glass doors.

4.95 out of 5 average rating, 218 reviews

Charming Studio

4.96 out of 5 average rating, 113 reviews

A modern building with a green roof is nestled in a lush landscape, surrounded by trees. Scenic views of rolling hills and the bay are visible in the background, offering a serene and natural atmosphere. The driveway leads up to the structure, enhancing accessibility.

Bungalow in Oakland

Modern 2 bedroom with stunning bay views

4.97 out of 5 average rating, 131 reviews

The living area features a comfortable full-size couch and a white accent chair. Large windows offer natural light and views of the surrounding landscape. A television is positioned on a low black console, while a dining area with bar stools complements the open layout.

Flat in Muir Beach

Muir Beach - Pacific Retreat

Guest suite in Half Moon Bay

A serene sunset reflects off the gentle waves of the ocean, casting golden hues across the water. The sky transitions from orange to soft yellow, with silhouettes of distant hills visible along the horizon, creating a peaceful coastal scene.

4.74 out of 5 average rating, 193 reviews

Super cute spot in awesome Half Moon Bay location