Family-friendly vacation rentals in San Mateo County

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautifully well-appointed cottage with a private entrance, designed for comfort, style, and privacy—ideal for couples, solo travelers, and business stays. The space is meticulously maintained to provide a clean, relaxing, and comfortable experience. Located within walking distance to Caltrain (0.9 miles) and downtown Redwood City (0.6 miles), offering access to boutiques, cafes, restaurants, parks, and a movie theater. Seamless access to Palo Alto, San Francisco and the greater Silicon Valley.

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

ADU studio unit in a 2/3 acre Spanish mansion

Kick back and relax in this calm, stylish beautiful mansion. An independent front ADU studio in a brand new modern Spanish style mansion in a 2/3 acre lot in Atherton with completely separate entrance and huge front yard with oak trees and fountain. Only 0.5 mile to 101 freeway and 1 mile to train station, near many high tech companies. A stylish welcoming king bed full Kitchenette large fridge large stove oven range microwave and in the unit washer dryer. Central AC and heat, internet & TV.

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.

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those inclined toward an active lifestyle, we are close to Purisima Creek, Huddart Park, and the El Corte de Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space)Note 20 minutes from Half Moon Bay with beautiful beaches and 30 min from Stanford in Palo Alto. We are adjacent to The Mountain House Restaurant. (note) The bed is a Murphy bed in the living area. NO PETS!

Luxurious 24’ Yurt in beautiful half acre garden

Nestled in the Santa Cruz mountains just 4 miles from the beach, 5 miles to Davenport and 9 miles from Santa Cruz (12 minutes by car) sits a magical Yurt situated in a beautiful private fenced half acre garden in Bonny Doon. Experience all that Santa Cruz has to offer then get away from the noise, traffic and bustle of the city and relax in this quiet and peaceful place situated above the fog line. Guaranteed to meet and likely exceed your expectations Dog, Child, and 420 friendly.

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.

Chic & Private Cottage on Mini Urban Farm

Feel right at home in this chic, private cottage in a rustic setting—a former Airbnb Plus listing! Relax amongst MCM furniture, luxurious bedding, fully-stocked kitchen, private patio with grill, and lush backyard. Ideal for families, friends, or business travelers. Convenient to Stanford Univ. and Hospital, and tech companies. Enjoy fresh eggs from our chickens when in season, and your choice of breakfast items for your first morning. Private entrance and off-street parking.

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

Eichler home w/ fire pit & private backyard

Step into a piece of Bay Area history. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated office w/ door - ideal for remote work - Wood-burning fireplace & open-concept living - 20 mins to SF | 15 mins to SFO | near Caltrain As of 6/12/26 there is one parking spot in the driveway, if you need two, let us know before check in

Caboose in the redwoods just outside of Cupertino

This rustic caboose is just 10 minutes from Cupertino and downtown Saratoga, perfect for both business travelers, outdoor adventurers, and everything in between. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else. Pets generally ok. Check with hosts. Pets must not be left alone.

Beachfront California Coast Airstream_Luxury (NEW)

This spectacular location comes fully equipped with the 'top of the line' 28 foot' Airstream, (Big Sur & Tommy Bahama class limited edition) with horizontal flip rear tail door for seamless indoor/outdoor living. Overlooking a stunning beach, perched high on a cliff this one of a kind experience boasts breathtaking views of the California coastline and Pacific Ocean to create an unforgettable magical experience of a lifetime.