Pet-friendly holiday rentals in Hillsborough

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.

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

Instant Booking Confirmation! Ample parking: Over-sized 2-car driveway! EV charging (12kW, level II, pay by kWh for EV charging, Tesla users: Please bring your own adapter) A charming, detached and private 3-bedroom, 2 bathroom house with a view to SFO on the Bay, Home Theater, Pool Table, Fully-Fenced Terrace Garden, Piano. WFH friendly: multiple desks, High Speed WiFi (100Mbps). Digital keypad entry for self check-in. You’ll have the entire house, backyard, front yard completely to yourself!

Outdoor spacesWalkabilityWi-Fi

4.94 out of 5 average rating, 362 reviews

4.96 out of 5 average rating, 201 reviews

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

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.

Outdoor spacesWalkabilityBarbecue

4.99 out of 5 average rating, 414 reviews

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.

Home in Half Moon Bay

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

Coastal Vacation House is a short 10 minute walk to Surfers Beach, Pillar Point Harbor & Sam's Chowder House! 15 miles/ 30 mins to San Francisco! Just a few blocks from the best restaurants, shops & Marina! Near ocean bluffs ( Mavericks) & Coastal Trail perfect for hiking, walking, bike riding. Short drive to downtown Half Moon Bay shops! Ideal for holidays & entertaining family on vacation! Fun for everyone including kids! The 2,100 sq ft home is cozy & roomy for a relaxing weekend in HMB!

WalkabilityPetsLocation

4.99 out of 5 average rating, 139 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.

Outdoor spacesPetsComfort

4.94 out of 5 average rating, 109 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

WalkabilityPetsNearby

4.98 out of 5 average rating, 132 reviews

The two-story house showcases a well-maintained exterior, featuring large windows framed with green accents. A charming porch is visible, along with a neatly landscaped yard. The driveway provides access to a two-car garage, and the peaceful neighborhood setting is enhanced by surrounding trees.

Home in Pacifica

Scenic Retreat w/ AC Hidden Gem Near SFO/SF/Beach

Welcome to our newest listing in the coastal town of Pacifica. This stunning house features a completely updated interior with brand-new furnishings and central A/C. In a beautiful and peaceful neighborhood, our house offers a unique blend of proximity to the ocean & mountains. From here, you can embark on a journey to explore the breathtaking scenery along Highway 1. San Francisco attractions or SFO are around 20 minutes away. Perfect place for family getaways or business trips.

WalkabilityOutdoor spacesBathroom

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.

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.

WalkabilityPetsDecor

4.96 out of 5 average rating, 423 reviews

4.97 out of 5 average rating, 386 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.

Guesthouse in Woodside

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

WalkabilityPetsCondition

4.95 out of 5 average rating, 313 reviews

The modern kitchen features white cabinetry and a sleek countertop. Open shelves display dishware and decorative elements. A stainless steel refrigerator and a dishwasher are visible, alongside a sink and a retro-style mint green toaster. Natural light enhances the welcoming atmosphere.

Home in Pacifica

Brighton Beach Cottage, One Bedroom plus Loft

Just a short stroll from Sharp Park beach and hiking trails our large private spacious 1 bedroom plus loft is perfect for your next beach and hiking getaway. Centrally located in the desirable Sharp Park neighborhood of Pacifica, you can get to San Francisco, Half Moon Bay, hiking trails, golf, and beaches quickly and easily. A few minutes drive to Linda Mar beach, one of the best surf spots in Northern California. The cottage is a single-family home.

Outdoor spacesWalkabilityLaundry

4.92 out of 5 average rating, 318 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

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!

Outdoor spacesWalkabilityAir conditioning

4.83 out of 5 average rating, 210 reviews

Guesthouse in Belmont

Treehouse w/ Canyon Views · King · Workspace · SFO

Wake up to canyon and oak-tree views from your private Belmont treehouse cottage—a quiet 2-bedroom guesthouse perched above the neighborhood with a deck, full kitchen, 360 Mbps wifi for remote work, and in-unit laundry. Self check-in via smart lock. ~15 min to SFO, 5 min to Belmont Caltrain. Great for Silicon Valley business trips, longer stays for relocators or remodels, and Bay Area event trips toward San Francisco, Palo Alto, and San Jose.

WalkabilityOutdoor spacesAir conditioning

4.95 out of 5 average rating, 124 reviews

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 Half Moon Bay

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

PetsWalkabilityWi-Fi

Popular amenities for Hillsborough pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

Outdoor spacesPetsIndoor spaces

4.88 out of 5 average rating, 109 reviews

Home in El Granada

Private Cottage House - Walk to Beaches Harbor

WalkabilityOutdoor spacesLayout

Home in South San Francisco

A modern kitchen features a spacious island with four high stools. White cabinetry surrounds a stylish backsplash of geometric tiles, complementing stainless steel appliances and ample countertop space, enhancing a well-lit and functional cooking area.

Modern Central 4BD/2.5Bath Home Near SF, SFO!

PetsOutdoor spacesHospitality

4.95 out of 5 average rating, 122 reviews

4.93 out of 5 average rating, 149 reviews

A two-story ocean view house is framed by a large tree, showcasing a welcoming entryway. A fenced yard is visible, and the distant ocean can be seen beyond the street. The neighborhood features a calm atmosphere with nearby coastal views.

Home in Montara

Ocean view house, beaches, trails, family friendly

WalkabilityPetsLong stay

4.93 out of 5 average rating, 215 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

PetsWalkabilityFamily

4.93 out of 5 average rating, 143 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

WalkabilityDecorAccess

4.91 out of 5 average rating, 212 reviews

The modern exterior of the house features a combination of wood and light-colored siding. A covered porch is highlighted by vertical lighting, while large windows provide views of the surrounding landscape. A manicured lawn and driveway contribute to the welcoming entryway.

Home in Mountain View

Upscale Modern House Near Mountain View Downtown

PetsWalkabilityValue

4.92 out of 5 average rating, 110 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

PetsOutdoor spacesLaundry

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 242 reviews

The modern complex is illuminated under the evening sky, showcasing a resort-style pool surrounded by lounge chairs and umbrellas. A vibrant rooftop area is visible, adorned with greenery and outdoor seating, while soft lights accentuate the building's contemporary architecture.

Apartment in Menlo Park

Spacious & Luxurious 1 BR w/Pool & Free Parking

PetsWalkabilityValue

Guesthouse 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.

The Willow Cottage

WalkabilityPetsHeating

4.94 out of 5 average rating, 145 reviews

4.98 out of 5 average rating, 253 reviews

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.

Guesthouse in San Rafael

Hillside Wellness Retreat | Pool, Gym & A/C

Outdoor spacesPetsLayout

4.96 out of 5 average rating, 115 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

PetsWalkabilityAccess

4.87 out of 5 average rating, 195 reviews

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.

Guesthouse in San Rafael

Farm in the city & sweeping bayview

WalkabilityOutdoor spacesBiking

4.88 out of 5 average rating, 121 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

WalkabilityOutdoor spacesIndoor spaces

4.92 out of 5 average rating, 100 reviews

A spacious living area is designed with a large L-shaped sectional sofa adorned with colorful throw pillows. A dark coffee table is centrally placed on a vibrant area rug, while natural light filters through large windows, enhancing the overall brightness of the room.

Home in Santa Clara

Silicon Valley Executive home in Santa Clara

WalkabilityValueSleep quality

4.91 out of 5 average rating, 233 reviews

A private outdoor area features a modern hot tub alongside a comfortable seating arrangement. Bright turquoise chairs offer a pop of color, while tall trees provide natural shade. The concrete patio is spacious, ensuring ample room for relaxation and enjoyment.

Home in Concord

Pool, Hot tub SFO, Napa, Clean Home

WalkabilityOutdoor spacesBarbecue

Private, pet-friendly home rentals

4.98 out of 5 average rating, 261 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

WalkabilityPetsIndoor spaces

4.97 out of 5 average rating, 155 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

WalkabilityOutdoor spacesView

4.8 out of 5 average rating, 257 reviews

The spacious living room features large glass doors leading to a scenic view outside. A comfortable couch with decorative pillows is situated near a kitchenette equipped with a full-size refrigerator and coffee maker. A striking wall mural of zebras enhances the unique decor.

Guest suite in Woodside

Central Woodside suite near restaurants with view

Outdoor spacesWalkabilityAmenities

4.83 out of 5 average rating, 6 reviews

Guesthouse in Burlingame

Guesthouse by Mills Canyon

PetsWalkabilityHospitality

5.0 out of 5 average rating, 43 reviews

Cottage in San Mateo

Sunny Private Escape | Gated, Peaceful & Safe

Outdoor spacesPetsQuiet

4.86 out of 5 average rating, 29 reviews

Home in Millbrae

Sunlit! New Luxury 3BR! Easy Parking!

Outdoor spacesWalkabilityFamily

4.96 out of 5 average rating, 52 reviews

A modern kitchen is highlighted by a large island with seating for four. Natural light floods in through the windows, which open to a balcony. Sleek cabinetry and stainless steel appliances are present, accompanied by a decorative plant near the entrance.

Home in Millbrae

Modern 3BR/3.5BA House with Parking & Laundry

Outdoor spacesWalkabilityAmenities