Family-friendly vacation rentals in San Mateo County

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.

Cozy & Fully Equipped Studio

Welcome to your perfect retreat! Our studio is fully equipped, modern, and super comfortable, offering all the amenities for an unforgettable stay. Whether you’re traveling for business or leisure, this space provides the ideal balance between comfort and convenience. 🛋 Cozy living area: Beautifully decorated with a comfortable sofa, TV 🍽 Fully equipped kitchen 🌿 Private patio: A perfect outdoor space to relax and enjoy fresh air. 🚗 Private parking with independent entrance self check in

Spacious home w/ fire pit & private backyard

Welcome to a beautifully renovated 1956 Eichler home in the San Mateo Highlands. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining area - Enclosed atrium w/ custom mural & red maple tree - Dedicated private office w/ door & Wi-Fi - ideal for remote work - Indoor fireplace & full kitchen - 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

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.

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Chic & Private Cottage on Mini Urban Farm

Feel right at home in this stylish, private cottage in a rustic, farm-like setting—previously Airbnb Plus! Relax amidst Mod furniture, luxurious bedding, a fully-stocked kitchen, private patio with grill, and lush yard. Perfect for families, friends, or business travelers. Convenient to Stanford University/Hospital, and all the tech companies. Enjoy fresh eggs from our hens when in season, and your choice of breakfast items for your first morning. Private entrance and off-street parking.

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!

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

Carmelita Creek House

The creek house is on a beautiful tree lined street, walking distance to downtown San Carlos. The house is a spacious one bedroom cottage with designer finishes and vaulted ceilings. You will be surrounded by mature redwoods and nature overlooking a year round creek. Amenities include a full sized kitchen, workspace, washer/dryer, fast WiFi, cable TV and a gas fireplace. Please note the cottage is located behind our main home and is accessed via several steps.

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.

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.