Holiday houses in San Mateo County

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Top-rated holiday rentals in San Mateo County

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Superhost

Home in Boulder Creek

4.88 out of 5 average rating, 250 reviews

The Artists' Tree House

STVR permit #221203. This charming home is perched in the trees with views of the forest through the skylights. Close to the mountain town of Boulder Creek if you need groceries. We aim to give you the most comfortable stay and modern amenities. If you are a remote worker, we have a work space in each bedroom with a large monitor and desk. Dogs are welcome. Smoking outdoors is permitted. Located 35min to Santa Cruz, 1:30 to downtown SF and 45min to San Jose. Hot tub under the redwoods and relax!

Top Guest favourite

Home in Half Moon Bay

5 out of 5 average rating, 115 reviews

Fabulous Beach Get Away - Brand New Beach House

Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

Top Guest favourite

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 221 reviews

Digital Nomad Retreat

Imagine yourself in the REDWOOD FOREST and take a breath of mountain air. Only 25 miles from the Silicon Valley, 15 miles from the Santa Cruz Boardwalk, a cozy location tucked in the forest. Many are on the move and can work from anywhere, so why not a beautiful place of your own? A perfect getaway spot central to WINE TASTING, HIKING, BEACHES and even mountain exploration, right from the doorstep. Located only a mile and a half from downtown Boulder Creek, food and window shopping are easy.

Guest favourite

Treehouse in Half Moon Bay

4.98 out of 5 average rating, 103 reviews

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.

Top Guest favourite

Home in Pacifica

4.97 out of 5 average rating, 102 reviews

Coastal Retreat w/ Ocean Views

Welcome to your dream coastal retreat! This stunning 4bd, 3ba modern home boasts breathtaking ocean views. Just minutes from the beach and a short drive to San Francisco, it's perfect for surfing, hiking, and relaxing. Unwind in the backyard hot tub after a day of exploring! Whether you're here to catch waves, explore trails, or simply relax with loved ones, our clean and stylish home offers the ideal setting for lasting memories. Book your stay and experience the ultimate luxury getaway!

Guest favourite

Tiny home in Half Moon Bay

4.86 out of 5 average rating, 656 reviews

Small Beach Cottage Near the Coastal Trail

This is the perfect place for a getaway near the beach. Tiny House provides you and your dog comfort and privacy in a quiet neighborhood close to the dog friendly Poplar Beach. We provide the basics to prepare small meals in our kitchenette. You have close access to miles of coastal trails, great shopping and dining in downtown (1 mile away). Ritz Carlton is just 2 miles South of us. The Harbor also has great options for dining. Many trails for hiking and biking very close by.

Guest favourite

Guest suite in Half Moon Bay

4.95 out of 5 average rating, 284 reviews

New! Oceanview Penthouse, 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.

Superhost

Townhouse in Pacifica

4.92 out of 5 average rating, 146 reviews

Stylish 4BR Ocean View Retreat - Modern & New!

This is our newest creation by a trusted Superhost. Make yourself at home in this bright and sunny space offering all the amenities of your own. Our open concept home includes a modern kitchen with stainless steel appliances, a open living room for entertaining, and fabulous deck with an ocean view! Located on a hill with breathtaking views of the Pacific Ocean. This professional designed home is 4 bedrooms / 3 baths that is located minutes from San Francisco. STR #14615101.

Guest favourite

Home in Pacifica

4.96 out of 5 average rating, 230 reviews

Brighton Beach Cottage, One Bedroom plus Loft

Just a short stroll from Sharp Park beach and hiking trails our large private spacious 1 bedroom plus loft is perfect for your next beach and hiking getaway. Centrally located in the desirable Sharp Park neighborhood of Pacifica, you can get to San Francisco, Half Moon Bay, hiking trails, golf, and beaches quickly and easily. A few minutes drive to Linda Mar beach, one of the best surf spots in Northern California. The cottage is a single-family home.

Guest favourite

Home in Boulder Creek

4.87 out of 5 average rating, 144 reviews

Victorian Cottage in the Redwoods

Historic Landmark 1899 Queen Anne Victorian Cottage near downtown Boulder Creek , Ca. Walking distance to bus, downtown restaurants, Wild Roots Market, hiking trails, San Lorenzo River. Recently remodeled 1 Bdrm 1 Bath with shower and bathtub Full kitchen Vitamix Organic Coffee Nearby Restaurants Beaches Surfing Mountain Biking Henry Cowell Redwoods State Park Roaring Camp & Big Trees Narrow Gauge Railroad Santa Cruz Boardwalk Wild Roots Market

Guest favourite

Apartment in Menlo Park

4.97 out of 5 average rating, 148 reviews

Charming 2BR Apartment near tech Giants & Stanford

Welcome to our Luxurious 2 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, two comfortable bedrooms, a pair of modern bathrooms, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

Top Guest favourite

Home in Half Moon Bay

4.99 out of 5 average rating, 147 reviews

Beautiful Seaside Retreat.

Enjoy the vast ocean views in this beautifully updated craftsman style home, one of the originals in the neighborhood. Stunning views from almost all of the windows of the house and the large deck will remind you that you are on vacation. Comfortable beds, modern kitchen, tasteful design and an amazing location close to beaches, harbor, trails, restaurants. bars, and cafes make tis place the perfect get away.