Holiday rentals with breakfast 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.

Value · Location · Nearby

Serene & Charming Home in Atherton border

Nestled in the border between Atherton & Redwood City CA, this exquisite property boasts privacy, tranquility, and natural beauty. With its serene surroundings, this house offers a truly idyllic retreat. The home offers a living room with large windows overseeing the front yard, a formal dining room with custom cork accent wall and French doors to the front porch. Three bedrooms, one ensuite and two serviced by a hall bath, complete the first floor, there is a recreation room above the garage.

Family · Location · Heating

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

Coastal Vacation House is a short 10 minute walk to Surfers Beach, Pillar Point Harbor & Sam's Chowder House! 15 miles/ 30 mins to San Francisco! Just a few blocks from the best restaurants, shops & Marina! Near ocean bluffs ( Mavericks) & Coastal Trail perfect for hiking, walking, bike riding. Short drive to downtown Half Moon Bay shops! Ideal for holidays & entertaining family on vacation! Fun for everyone including kids! The 2,100 sq ft home is cozy & roomy for a relaxing weekend in HMB!

Location · Family · Back garden

Cozy quiet Cabin w/Firepit-walk to Beach & Harbor

Guesthouse in quiet neighborhood. Short walk to Surfer’s beach. Near harbor, restaurants & Spangler’s market. Bike ride or stroll the paved coastal bluff trail. Kayak in the harbor. Hiking in the hills behind the cottage in Quarry Park. Full kitchen. Attached covered deck. Cable TV & WIFI. Queen size memory foam bed. Sit around the outdoor firepit at night-see the stars & hear the ocean waves and seals. Brew pubs & live music in the Harbor. Shopping & Festivals on Main Street, 3 miles away.

Family · Location · Access

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!

Location · Value · Bathroom

Chic & Private Cottage on Mini Urban Farm

Feel right at home in this stylish and private Mid-Century cottage, situated in a rustic, farm-like setting. 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 and Hospital, and 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.

Value · Family · Layout

Entire guest unit in Portola Valley near Stanford

Tucked into the foothills of Portola Valley, this guest unit offers a rare blend of comfort, and natural beauty. Surrounded by majestic oak trees and rolling hills, the setting feels like a quiet retreat—yet you’re just minutes from Palo Alto, Stanford, and the best of the Bay Area. It's got 1 bedroom, a large living room, kitchenette, desk, and full bath. Whether visiting for business, academia, or a getaway, this thoughtfully designed space provides a calm, welcoming home base.

Location · Hiking · Comfort

Spacious 6‑BR Home Minutes from SF

This 6-bedroom home offers the perfect blend of space, comfort, and convenience - just minutes from San Francisco. With a bright open living area, fully stocked kitchen, and thoughtfully furnished bedrooms, it’s ideal for families or groups. Enjoy a large backyard for BBQs and playtime, all in a quiet, family-friendly neighborhood close to parks, shops, and city access. Whether for work or a family trip, this warm and welcoming home has everything you need for a comfortable stay.

Location · Value · Accuracy

Comfortable 1 Bedroom In-Law near SFO/BART

Comfortable, brand new 1 bedroom 1 bathroom in-law perfect for couples and solo travelers. Includes a full kitchen and living room in addition to other amenities. Located in a quiet neighborhood. Accessible through a private entrance at the side of the house. Street and private parking available. Close to SFO, 101, and 280 freeways, 10 min walk from BART and Caltrain, and 15 min walk from Millbrae downtown where convenience stores, markets and restaurants are all located.

Family · Location · Checkout

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Value · Location · Heating

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.

Location · Family · Accuracy

STAR WARS: Cozy, Kid & Pet Friendly, Private Entry

Welcome to San Francisco! Star Wars fans, enjoy our newly remodeled, galaxy-themed space. Located in San Leandro, perfectly between SF and Silicon Valley, with easy access to BART and a shopping mall. Kids love the ball pit! Well-behaved dogs are welcome for a $100 pet fee, so enjoy a cozy stay with your furry friend.

Family · Location · Heating