Family-friendly vacation rentals in Woodside

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Woodside

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Sunnyvale

4.97 out of 5 average rating, 274 reviews

Comfortable, Modern, Bright w/Patio

A completely separate private guest suite in a beautiful house, furnished with love and all the amenities you'd need. Also, super walkable & safe location, fast wifi, comfy beds, friendly experienced hosts ready to help you with whatever you need. Look forward to soaking in the sun on the patio, and enjoying the park across the street. It's a 10min walk to the great bars & restaurants downtown SV, or to the Caltrain station for a hassle-free trip to SF or SJ. We love living here and so will you!

Jul 29 – Aug 5

R2,522 ZAR per night

Guest favorite

Guesthouse in Redwood City

4.97 out of 5 average rating, 177 reviews

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautiful cottage constructed with its own entry, offering beauty, comfort and privacy for your travel needs. Great location for couples, solo & business travelers alike. Cottage well appointed with many travel needs. Expertly maintained and cleaned. Walking distance to Caltrain (.9 mile), bustling downtown Redwood City (.6 mi), boutiques, coffee, restaurants, parks, movies (1.1 mi) & 5 miles to Palo Alto. Easy access to San Francisco, San Jose and the Silicon Valley. CVD Vaccinated Hosts.

Oct 17 – 24

R4,542 ZAR per night

Guest favorite

Cabin in Woodside

4.97 out of 5 average rating, 342 reviews

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!

Aug 3 – 10

R3,471 ZAR per night

Superhost

Guest suite in Los Altos Hills

4.8 out of 5 average rating, 148 reviews

A private hillside suite nestled among oaks

Better than the Four Seasons or the Rosewood! Beautiful, compact, private in-law suite in the walk out basement of our modern home. Enter via outdoor stairs from parking area to suite. Serene bay views and lush greenery below grand oaks. Your suite has a very comfortable King bed, Japanese washlet, closet space, TV, wi-fi, private washer/dryer, fully equipped kitchen with gas stove, microwave, fridge/freezer & dishwasher. Ceiling fan, radiant in-floor cooling/heating. Private parking. 280 SF.

May 23 – 30

R3,061 ZAR per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 340 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

Oct 11 – 18

R2,728 ZAR per night

Guest favorite

Guest suite in Cupertino

4.96 out of 5 average rating, 376 reviews

Modern Suite in Cupertino

Nice quiet location. Bright, tranquil, and comfortable unit in a private house with a separate entrance and private yard. Unit consists of one bedroom, one bathroom, and a kitchen and living area. House is within walking distance of Cupertino Library, De Anza College, and top Cupertino schools. Very close to nearby Silicon Valley high-tech companies. Prime Bay Area location with high accessibility to public transporation, eateries, and entertainment.

May 26 – Jun 2

R2,748 ZAR per night

Guest favorite

Home in Redwood City

4.97 out of 5 average rating, 290 reviews

Private suite

Our home offers a private getaway perfect for business or a place to relax outside the city. Enjoy your private deck, complete with jacuzzi, and enter our large, sunny suite. Features Cal-King bed, on suite bath with heated tile flooring and bluetooth shower speaker. On site kitchenette includes mini bar, microwave, toaster oven, coffee maker & fridge/freezer. High speed WIFI connection and desk for workspace. Smart TV with blu ray, DVD, and cable.

Jun 22 – 29

R2,803 ZAR per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 483 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Jan 4 – 11

R3,974 ZAR per night

Guest favorite

Guesthouse in Atherton

4.99 out of 5 average rating, 174 reviews

Charming Cottage near Stanford in Lovely Garden

Relax in our light and airy cottage situated in a beautiful garden setting, the perfect get-away after a day of business meetings or visiting with family. We are close to major Silicon Valley destinations; 45 minutes from San Francisco, San Jose and the beach in Half Moon Bay — easy access to Highways 101 and 280. Our quiet neighborhood full of mature oak trees beckons you to take a walk.

Jan 8 – 15

R3,361 ZAR per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 810 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. Due to the coronavirus, we are 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.

Dec 1 – 8

R2,687 ZAR per night

Guest favorite

Guesthouse in Menlo Park

4.9 out of 5 average rating, 352 reviews

Cottage near downtown Palo Alto

FOR YOUR PEACE OF MIND A THOROUGH DISINFECTANT CLEANING IS COMPLETED BEFORE EVERY RESERVATION. Cottage located a discrete distance behind a private home in a family neighborhood. Within walking distance to downtown Palo Alto. Parking for a single car next to the front door of the cottage.

Oct 2 – 9

R2,880 ZAR per night

Superhost

Home in East Palo Alto

4.82 out of 5 average rating, 945 reviews

Cozy private guesthouse near Stanford

This is our nice, new and adorable cottage in the backyard. Beautiful house, very private and clean. 340 sq feet. Biking distance to Stanford University and top Silicon Valley companies as well as to Caltrain station. Close to freeway 101, 84 and 880. Sorry, no pets, no TV, no smoking!

Oct 18 – 25

R2,225 ZAR per night