Holiday houses in San Mateo County

Poplar Beach Getaway: Family-Friendly, Near Beach!

Family-friendly, relaxed home in a quiet residential neighborhood - 1/2 block from the blufftops, a 10-minute stroll to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops, and cafes. 3 bedrooms with queen beds, two baths, a living area, a well-equipped kitchen, a spacious kid-friendly den, and a backyard with a new deck ensure you all have room to spread out and relax after a fun day at the beach or exploring the area. Short drive to San Francisco, Santa Cruz, San Jose.

Value · Location · Indoor spaces

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Location · Value · Sleep quality

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!

Family · Value · Wi-Fi

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.

Location · Value · Solo travel

Eichler Home w/ Fire Pit & Private Backyard

Step into a rare 1956 Eichler home in San Mateo - mid-century architecture, a private backyard, and everything you need to work, unwind, or explore the Bay Area. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private fenced backyard w/ fire pit, BBQ & 8-person dining area - Enclosed atrium w/ custom mural & red maple tree - Dedicated office w/ door & fast Wi-Fi throughout - Wood-burning fireplace, full kitchen & in-unit washer/dryer - 20 mins to SF | 15 mins to SFO | near Caltrain

Value · Location · Sleep quality

SFO 10 min, Stylish Suite, Walk to Grocery

Ten minutes to SFO, a short walk to Caltrain, and one block from cafés and restaurants— this private San Mateo suite is the ideal Bay Area base for business travelers, airport transits and couples exploring the peninsula. Settle into a comfortable queen bed with room-darkening shades, pull up a dedicated workspace with 789 Mbps WiFi, and unwind with Netflix, HBO Max, Disney+, Hulu, or Amazon Prime on the smart TV. Everything is taken care of so you can focus on why you're here.

Family · Location · Outdoor spaces

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Family · Location · Sleep quality

New- Stunning Oceanfront "Pelican Bluffs"

Perched on a dramatic oceanfront bluff, Pelican Bluffs fuses modern comfort with coastal charm. Gaze at pelicans gliding over crashing waves, create masterpieces in the the gourmet kitchen, enjoy playful havens for family time, and find workspaces where inspiration abounds. End your day, gathered around the gorgeous fire pit as the fiery sunset turns into a canopy of stars and unforgettable memories see additional photos section for prior reviews from an earlier host

Family · Location · Shared spaces

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

Family · Value · TV

Serene Modern Home with Yard & Parking

This spacious, tastefully decorated and full of natural light large house is a perfect combination of comfort and style. The house is recently renovated and has got everything to accommodate all your needs for a perfect stay. Convenient strategic location and easy commute to SF, Silicon Valley, BART and Airport, full amenities, parking, safe and quiet neighborhood, professionally managed, immaculately clean and more. Book now before someone else does!

Family · Location · Laundry

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 · Nearby

Sea Wolf Bungalow

If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.

Value · Location · Amenities