Family-friendly holiday 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.

4.98 out of 5 average rating, 448 reviews

A cozy living area features a gas fireplace, providing warmth. A television is mounted above, and natural light enters through two windows. A round red rug is positioned on the hardwood floor, with a light-colored sofa and a dark chair visible, creating an inviting space.

Guest house in Woodside

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Treehouse in Half Moon Bay

A bright interior space features large windows allowing natural light to fill the area. Colorful cushions in various shades are arranged on the floor, complemented by wooden accents and an open ceiling design that highlights the natural surroundings.

4.99 out of 5 average rating, 138 reviews

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

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.

Guest house 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

4.97 out of 5 average rating, 459 reviews

A private deck area is surrounded by lush greenery and colorful shrubs. A large umbrella provides shade over the wooden table and chairs, inviting relaxation outdoors. The deck is accessible from the yard, enhancing the tranquil outdoor experience.

Flat in Burlingame

Home away from home in beautiful Burlingame!

It's my honor to be your host and I will try to make your stay really great. Please let me know if you have any questions ahead of time as I want to make sure you have the best visit. Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price reflects that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

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.

Guest house 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. *

Guest house 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, 990 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 bright sleeping area features a gold bed frame with crisp white linens. An accent pillow adds a pop of color. A nightstand holds a small lamp, while a window displays greenery outside, enhancing the inviting and serene ambiance of the room.

Home in San Mateo

Comfortable 3BR stay w/ fire pit

Welcome to your cozy Bay Area retreat - a calm, inviting space for fireside evenings & easy gatherings. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Wood-burning fireplace & backyard fire pit - Enclosed atrium w/ custom mural - Kitchen & dining area plus dedicated workspace - Private backyard - fully fenced - Air conditioning, heating, WiFi, in-unit laundry

Guest house in Burlingame

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.

4.98 out of 5 average rating, 340 reviews

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.

Guest house 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.

Guest house in Oakland

Guesthouse Garden Retreat

4.84 out of 5 average rating, 289 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, 110 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, 177 reviews

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

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley

4.92 out of 5 average rating, 146 reviews

Home in Montara

Entire Private Coastal Retreat - Spectacular Ocean

Family- and pet-friendly home rentals

4.95 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.

Guest house 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

4.93 out of 5 average rating, 166 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

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.

Guest house 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

Apartment in Civic Center

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.

4.9 out of 5 average rating, 312 reviews

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.

Guest house 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.

Guest house in Woodside

Rustic Cabin in the Redwoods

4.88 out of 5 average rating, 185 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!

Guest house 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