Family-friendly vacation rentals in Hillsborough

4.87 out of 5 average rating, 123 reviews

A light-filled living room features a comfortable white sofa and a stylish armchair, positioned around a wooden coffee table. A modern television is mounted above a decorative stone fireplace. Soft curtains frame the window, enhancing the open feel of the space.

Home in San Mateo

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!

Guest suite in Burlingame Hills

The bedroom features a spacious bed with white bedding, complemented by decorative pillows. A blue accent chair sits nearby, next to a decorative bedside table with a lamp. Natural light filters in through a window with white shutters, illuminating the light-colored walls and geometric rug.

4.88 out of 5 average rating, 131 reviews

Gorgeous Suite close to SFO Airport, Self Check-In

Enjoy a peaceful stay at this newly appointed luxury suite. Burlingame is a suburb of San Francisco, known for it's tree-lined streets. Close to downtown San Mateo and Silicon Valley. This suite is part of a beautiful Spanish style house with a private entrance. Minutes from shops and restaurants Broadway Burlingame and Burlingame Avenue. Perfect for business travelers, couples or solo adventures! Features queen size bed, smart TV, refrigerator, microwave, Light and Bright! Wi-Fi, Parking.

4.78 out of 5 average rating, 789 reviews

A cozy living area features a grey sofa adorned with colorful cushions. A sleek black coffee table sits in front of a modern television, with a decorative plant nearby. Bright yellow curtains covered in floral patterns frame the window, allowing natural light to illuminate the space.

Guest suite in Millbrae

Private 1 bedroom suite for quick SFO trip withA/C

1 bedroom 1 bathroom guest suite with private entrance. Good for a short SFO trip. But be aware it might not fit family vacation need! Newly remodeled kitchen, full bathroom, Wi-Fi, gas cooktop, coffee maker, toaster, microwave. Soft foam topper queen bed. Convenient for Bay Area commuter, 15 mins driving to SFO airport. Close to 101, 280 freeway. 30 mins driving to San Francisco or 50 mins to San Jose. 15 mins walk to grocery store, Starbucks and restaurants. Easy and free street parking.

4.92 out of 5 average rating, 116 reviews

A spacious living area features a light grey couch adorned with patterned cushions, situated in front of a glass-topped table. A small succulent plant and coasters are placed on the table, with glimpses of a neat kitchen and a dedicated sleeping area visible in the background.

Guesthouse in Belmont

A private and quaint gateway on Belmont Hills

Welcome to our cozy Belmont studio! This charming retreat offers a comfortable stay with its stylish design, fully equipped kitchen, and a comfortable bed. Conveniently located in Belmont, CA, you'll be close to vibrant San Mateo downtown, the scenic coastline of Half Moon Bay, and the airport. This quaint studio is tucked away on a small hill, surrounded by greenery. As a delightful bonus, you'll find a lovely lemon tree in the driveway, providing complimentary lemons for your stay.

4.95 out of 5 average rating, 160 reviews

A spacious sleeping area features a queen-sized bed with a neutral-toned blanket, accompanied by bedside lights. A desk with a chair is positioned near a window, allowing natural light to brighten the room. A lounge chair and wall-mounted TV are visible in the corner.

Guest suite in Belmont

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

4.78 out of 5 average rating, 102 reviews

The studio features vaulted wooden ceilings and a spacious layout. A king bed is positioned near a large window, providing natural light. A smart TV is placed on a stand, while a kitchenette can be seen in the background, equipped with modern appliances.

Guest suite in San Mateo

246C - Large Studio w/ Kitchenette, Laundry & Deck

This is a spacious, modern, and newly remodeled studio unit in our beautiful home located in the center of Hillsdale. This studio features a king bed, smart TV, private bathroom, large kitchenette and wet bar, in-unit laundry, and a spacious SHARED deck with the main unit. It is 2 blocks from San Mateo Medical Center, and only a mile away from Hillsdale Shopping Center & Traders Joe's. There are many restaurants & shops nearby. This studio is accessed from the backyard deck.

4.92 out of 5 average rating, 165 reviews

A cozy sleeping area features a spacious bed with neutral-toned bedding. Two bedside lamps provide illumination, while a comfortable chair complements the room. Light wood flooring adds warmth to the space, contributing to a well-designed, inviting environment.

Guesthouse in San Mateo

Cozy Studio 1B/1B w A/C No Pet in San Mateo

This cozy studio is good for a couple 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

4.98 out of 5 average rating, 380 reviews

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

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.

4.94 out of 5 average rating, 118 reviews

A modern studio bedroom features a spacious queen-size bed, dressed in a light blue quilt. Two large windows allow natural light to fill the room, complemented by a small working desk and chair. Neutral tones create a calming environment.

Guest suite in Belmont

New, modern quiet private studio

New modern private studio attached to the main house with a private staircase entrance. Easy free parking in front of the entrance. Located in heart of the Bay Area: 15 minutes to SFO airport, 19 minutes to Half Moon Bay, 17 minutes to Stanford. Enjoy nice views with morning coffee. Ideal for 1-2 guests. Working desk, wifi, tv, comfortable linens, small fridge, microwave and Phillips coffee machine.

4.93 out of 5 average rating, 239 reviews

The entrance to the studio features double glass doors framed by potted plants and flowers in various sizes. A welcome mat is positioned at the threshold, and small wall-mounted lights provide illumination. Natural light can be seen streaming through the doors.

Guesthouse in San Mateo

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Guesthouse in Hillsborough

A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.

4.95 out of 5 average rating, 991 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Since the coronavirus pandemic, we have been taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

4.98 out of 5 average rating, 340 reviews

A cozy sleeping space features a queen bed with white linens and colorful decorative pillows. A light fixture stands beside the bed, and a wall art piece composed of natural materials adds interest. A closet with sliding doors is visible in the background.

Guesthouse in Burlingame

Clean&Cozy Cottage near downtown Burlingame & SFO

Our sunny backyard cottage, with outdoor private entry, is centrally located in Burlingame between Burlingame Avenue and Broadway and is a great spot suited to a business traveler in search of a home away from home while also being ideal for vacationers looking to live like a local, only miles from SF. Enjoy and unwind!

Popular amenities for Hillsborough family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 270 reviews

A tranquil garden area features lush greenery, with tropical plants surrounding a private hot tub. Soft lighting highlights the space, creating a serene ambiance. A pathway leads to the entrance of the suite, ensuring privacy and easy access for guests.

Guest suite in Mission

Mission Private 1BR/BA Garden Suite Separate Entry

4.88 out of 5 average rating, 269 reviews

A cozy cottage is surrounded by lush greenery and a variety of shrubs. Stairs made of bricks lead up to a welcoming entrance with multiple windows that allow natural light to fill the interior. The setting is serene, with trees enhancing the tranquil atmosphere.

Guesthouse in Belmont

Private Garden Cottage in Belmont Hills

4.99 out of 5 average rating, 389 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

4.92 out of 5 average rating, 379 reviews

The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.

Guesthouse in Oakland

Guesthouse Garden Retreat

4.96 out of 5 average rating, 130 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

4.84 out of 5 average rating, 290 reviews

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.

Home in Miramar

Studio: Hot Tub + ocean view

4.96 out of 5 average rating, 633 reviews

A spacious bathroom features onyx marble surfaces and natural light streaming through skylights and large windows. A jetted bathtub is positioned beside a dual-sink vanity with rich wooden cabinetry. Plush bath mats add comfort, enhancing the serene and elegant atmosphere.

Guest suite in Daly City

Romantic Spa Suite — Whirlpool•Balcony•Luxe Escape

4.92 out of 5 average rating, 146 reviews

Home in Montara

Entire Private Coastal Retreat - Spectacular Ocean

Family- and pet-friendly home rentals

4.81 out of 5 average rating, 135 reviews

A spacious deck is showcased, featuring a vibrant red umbrella providing shade over a circular table. A hammock with colorful stripes is visible, gently swaying in the sunlight. Surrounding greenery creates a serene backdrop, enhancing the outdoor relaxation spaces.

Home in San Carlos

Canyon Oak House: Private, tranquil with trees

4.95 out of 5 average rating, 469 reviews

The interior of the cabin features a single bed dressed in a blue and white plaid coverlet alongside two soft pillows. A kitchenette area with wooden cabinets and a small fridge is visible, complemented by a round mirror and decorative wall art of a forest scene.

Guesthouse in La Honda

Bicycle Shack @ La Honda Pottery

4.96 out of 5 average rating, 270 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

Townhouse in Half Moon Bay

A comfortable living area showcases a white sofa and two black armchairs arranged around a glass coffee table. A series of ocean-themed canvases adorn the wall, with a flat-screen TV mounted nearby, providing a relaxing space for guests.

4.96 out of 5 average rating, 334 reviews

Seaside Retreat - newly remodeled!

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, 366 reviews

Oceanview Penthouse, Stylish, Walking to Beach

4.97 out of 5 average rating, 328 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

4.89 out of 5 average rating, 388 reviews

A spacious property is nestled among tall, lush trees, with a distinct white exterior. A wide driveway leads to the entrance, complemented by a covered porch area. Natural stone landscaping is visible along the side, blending harmoniously with the surrounding forest.

Guest suite in Woodside

Stay Nestled in Ancient Redwoods in Silicon Valley

4.94 out of 5 average rating, 140 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

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 312 reviews

A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.

Condo in Civic Center

Lakeside Retreat (w/ private parking)

4.91 out of 5 average rating, 176 reviews

A charming tiny house is nestled among towering redwood trees, featuring a red door and a large window. Potted plants line the front steps, and a small patio area with red chairs and a table invites outdoor relaxation.

Tiny home in La Honda

Delightful Tiny Home in the Redwoods !

4.96 out of 5 average rating, 285 reviews

An outdoor lounge area features a sectional sofa arranged around a fire pit, illuminated by warm flames. The pool glistens in the background, surrounded by lush greenery and gently lit by the evening sky. The setting offers a tranquil atmosphere for relaxation.

Guesthouse in Oakland

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

4.88 out of 5 average rating, 467 reviews

A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.

Guest suite in Woodside

Separate entry room near Stanford

4.99 out of 5 average rating, 350 reviews

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guesthouse in Woodside

Rustic Cabin in the Redwoods

Guest suite in Walnut Creek

A tranquil swimming pool is surrounded by lounge chairs, nestled among lush greenery and tropical plants. The two-story house features large windows, allowing natural light to brighten the space, while a path leads to the garden area.

4.99 out of 5 average rating, 621 reviews

Garden Oasis Suite with Spa and Pool, Walnut Creek

Guesthouse in Walnut Creek

A hot tub is positioned on a wooden deck, surrounded by tall trees and lush greenery. Two lounge chairs are set nearby, offering a relaxed space for guests to enjoy the serene environment.

4.91 out of 5 average rating, 620 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown