House holiday rentals in San Mateo County

4.96 out of 5 average rating, 255 reviews

The sunroom features expansive glass windows that offer a panoramic view of the city and hills at sunset. A cozy seating area with a light blanket and soft cushions is present, providing a relaxing space to enjoy the scenic landscape.

Home in Daly City

SF Amazing View & SUNroom: Spacious Private 1 bdrm

👋 Welcome to our spacious, clean, private getaway studio on Southern Hill in Daly City. Escape the hustle and bustle of the city. Enjoy a stunning view of day/night in clear days ☀️ - Easy street parking - Great Summit Loop Trail at San Bruno Mountain (6-min🚘) - Cow Palace Arena (8-min🚘) - H Mart grocery mall (10-min🚘) - 9.2 miles to SFO (17-min🚘) - 6.7 miles to Civic Center（>30-min🚘 w/ traffic or 20-min🚘 w/o traffic) - 11 miles to Fisherman's Wharf(>35-min🚘 w/ traffic or 23-min🚘 w/o traffic)

4.91 out of 5 average rating, 399 reviews

Poplar Beach Getaway - Special Pricing!

Family-friendly, relaxed home located in a quiet residential neighborhood - 1/2 block from the coastal open space, a 10-minute walk to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops and cafes. 3 bedrooms with queen beds, two baths, living area, well-equipped kitchen, spacious kid-friendly den and backyard with deck ensure that you 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.

4.92 out of 5 average rating, 174 reviews

A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.

Home in Portola Valley

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

A modern living area features a sectional sofa complemented by a glass coffee table. Large sliding doors provide natural light and a view of the outdoor space. A sleek fireplace adds warmth to the room, with a stylish area rug enhancing the comfortable setting.

5 out of 5 average rating, 144 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.

A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.

4.96 out of 5 average rating, 174 reviews

Stairway to Heaven - 2 bedroom

PLEASE NOTE, we live in a 3 story home and this unit is on the lower level of our home. Also available in a 1 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

4.94 out of 5 average rating, 103 reviews

Home in Redwood City

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

4.95 out of 5 average rating, 144 reviews

An open-concept living area is highlighted by a wood-burning fireplace with a textured white surround. Mid-century furniture, including a leather sofa and colorful chairs, is arranged around a plush area rug, while large windows provide natural light and views of the outdoor space.

Home in San Mateo

Eichler home w/ fire pit & private backyard

Step into a piece of Bay Area history - a 1956 Eichler home w/ mid-century character, a private backyard fire pit & dedicated workspace. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ, 8-person outdoor dining & enclosed atrium - Dedicated office w/ door & fast Wi-Fi - great for remote work - Wood-burning indoor fireplace & open-concept living - In-unit washer/dryer, full kitchen & 42" TV w/ streaming - 20 mins to SF, 15 mins to SFO - free parking on premises

The exterior of the property is showcased, highlighting its unique architectural design with wooden paneling and large windows. A staircase leads to the entrance, and lush greenery is visible in the background, enhancing the coastal setting.

4.95 out of 5 average rating, 158 reviews

Luxury Ocean Front & Harbor View Home

Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Half Moon Bay, this stunning property is the perfect destination for your next coastal retreat. The two-bedroom, three-bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Half Moon Bay throughout the common areas and bedrooms. This is the ultimate in coastal luxury, featuring modern appliances and an open floor plan through all the common areas.

4.96 out of 5 average rating, 306 reviews

The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.

Home in San Carlos

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 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).

4.95 out of 5 average rating, 139 reviews

A sunlit dining area is framed by large windows that provide a clear view of the ocean and sunset. A small round table is set with two black chairs, and a woven basket sits at the center, while a soft rug covers the floor.

Home in Moss Beach

Oceanfront Oasis, Sunsets & Crashing Waves

The Bluffs Oceanfront Oasis awaits you. Our beautifully appointed home sits right on the cliff boasting crashing waves and endless sunsets. Start your day in the zen room for a bit of yoga and meditation or take a leisurely walk on the beach trail right out the back gate. After dining out or in, end your evening with something special while seated at the firepit over looking the Pacific. Come for a romantic getaway, a weekend of golf or a family fun filled vacation.

4.98 out of 5 average rating, 401 reviews

The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.

Home in Montara

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

A spacious grassy yard is surrounded by lush gardens, showcasing colorful flowers and greenery. A seating area with wooden chairs is situated near a fountain, providing a tranquil spot to enjoy the views. The sky displays varying shades of blue, contributing to the serene atmosphere.