Family-friendly holiday rentals in Hillsborough

Guesthouse in Redwood City

A charming cottage entrance is framed by natural wood shingles and surrounded by lush greenery. A small porch is adorned with a wicker chair and colorful cushion, inviting guests to enjoy the serene outdoor space. Sunlight filters through the trees, illuminating the pathway.

4.93 out of 5 average rating, 352 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

4.88 out of 5 average rating, 121 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, 784 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, 113 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.

4.92 out of 5 average rating, 164 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

Guesthouse in Park Pacifica

A well-lit guestroom features a queen-size bed with floral bedding. A spacious loveseat sofa is positioned near a sliding glass door that opens to the backyard. A small coffee table rests in front of the sofa, and a portable air conditioner is visible in the corner.

4.97 out of 5 average rating, 523 reviews

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

4.95 out of 5 average rating, 117 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, 238 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, 984 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.

4.95 out of 5 average rating, 139 reviews

A vibrant yellow dining table set for eight is positioned in a spacious open-plan area, surrounded by natural light from large glass doors. A soft, textured light fixture hangs overhead, complementing the modern aesthetic. The backdrop features a landscaped outdoor space visible through the glass.

Home in San Mateo

Cozy 3BR stay w/ fireplace & fire pit

Welcome to your calm Bay Area retreat - a cozy spot for fireside evenings, easy indoor-outdoor living & Super Bowl weekend stays! - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural - Wood-burning fireplace & backyard fire pit - Kitchen & dining area plus dedicated workspace - Private backyard - fully fenced - Air conditioning, heating & in-unit laundry

4.95 out of 5 average rating, 200 reviews

A modern guest suite is highlighted by a queen bed with crisp white linens against a neutral wall. Two large windows provide natural light, accompanied by elegant curtains. A stylish chair and small table create a cozy seating area, while a mirror and plants add to the inviting decor.

Guest suite in San Bruno

Stylish Private Guest Suite Near SF and SFO

Welcome to our stylish Guest Suite! This modern retreat is perfectly situated near San Francisco and SFO, offering you convenience and comfort. With thoughtfully designed interiors, a comfortable bed, and amenities to enhance your stay. Conveniently located 10 min drive from SFO Airport and 15 min drive from San Francisco.

Popular amenities for Hillsborough family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 179 reviews

A living area features a blue sofa adorned with decorative pillows and a light blue area rug. A white desk with a green chair is positioned against a turquoise accent wall. Soft light is present, illuminating the entrance to the hallway in the background.

Condo in Pacifica

Game room, 20 min to SF, hot tub, beach 1 block

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, 268 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

4.92 out of 5 average rating, 378 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, 128 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, 287 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

4.91 out of 5 average rating, 109 reviews

A living area is presented with a comfortable black couch and two accent chairs. A wooden coffee table sits centrally, complementing a flat-screen television. The space features an open kitchen with white cabinets and modern appliances. Sliding glass doors lead to a private outdoor area.

Guest suite in Montara

Montara Beach Getaway

4.96 out of 5 average rating, 631 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

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, 467 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, 267 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

4.87 out of 5 average rating, 127 reviews

The open living area features a comfortable sofa and a dining table with two chairs. A well-equipped kitchenette is visible, along with a large TV set against the wall. Natural light brightens the space through a window, enhancing the welcoming environment.

Guesthouse in Stonestown

Newly Remodel Guest Suite-Separate Entrance

Guesthouse in Half Moon Bay

The living area features a blue velvet sofa and a white upholstered couch, positioned around a wooden coffee table. Two framed photographs adorn the green walls, with light filtering through nearby windows. A decorative plant hangs in one corner, adding a touch of greenery.

4.88 out of 5 average rating, 336 reviews

Stylish Spacious Seaside Retreat, 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, 387 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, 138 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, 175 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, 282 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, 466 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, 348 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

4.88 out of 5 average rating, 184 reviews

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

Little Poolside House near Downtown Mountain View!

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, 618 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown