Vacation rentals with a pool in San Mateo County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Mateo County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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.

4.93 out of 5 average rating, 179 reviews

Top guest favorite

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guesthouse in Woodside

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.

4.99 out of 5 average rating, 379 reviews

Guest favorite

A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.

Guest suite in Woodside

Separate entry room near Stanford

This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

4.88 out of 5 average rating, 487 reviews

Superhost

A living area features a spacious couch adorned with decorative pillows, accompanied by a colorful armchair and a stylish coffee table. Natural light filters through patterned curtains, illuminating the room. A work desk is positioned nearby, enhancing the functional layout of the space.

Apartment in Redwood City

Homey 1 bedroom with Pool near Stanford Hospitals

Enjoy a stylish stay at this centrally located place in Redwood City, close to Hospitals (like Stanford and more), high-tech companies, and major Silicon Valley employers. But it's not all work here in Redwood City. We have a vibrant downtown with life music venues, festivals, wide variety of restaurants and nightlife. With its close proximity to Half Moon Bay and Woodside, there are beaches to explore or beautiful Redwood forests available for hiking and exploring. Hope to see you soon!

5.0 out of 5 average rating, 5 reviews

Guest favorite

A scenic pool area is framed by tall pine trees, with a vibrant sunset reflecting in the calm water. The landscape features gentle hills in the background, enhancing the serene environment.

Home in Ben Lomond

The Hacienda- Santa Cruz Mountain Ridgetop Retreat

"Welcome to the Hacienda", a modest mid-century retreat located in the beautiful Santa Cruz Mountains. The Hacienda is located just 5 minutes from Ben Lomond town, 10 minutes from Henry Cowell State Park and only a 20 minute drive from Santa Cruz beaches. Our unique private home includes a pool & hot tub which sits on the ridgetop overlooking the gorgeous San Lorenzo Valley. If you're looking for peace & tranquility or simply need to relax and recharge, the Hacienda awaits your arrival.

4.95 out of 5 average rating, 125 reviews

Guest favorite

Home in Mountain View

Cozy 2BR w/ Patios, Prime Mountain View Location

Welcome to your perfect Mountain View getaway—an inviting 2-bedroom, 2.5-bath home designed for comfort, convenience, and relaxation in the heart of Silicon Valley. This thoughtfully designed space features two spacious bedrooms each with its own private en-suite bathroom & outside patio, offering privacy and comfort for families, couples, or business travelers. You're minutes away from Downtown Mountain View, Castro street dining, Civic Center, Google, and Caltrain.

4.88 out of 5 average rating, 25 reviews

Guest favorite

A two-story home is surrounded by well-maintained grass and trees. The front features a welcoming porch with two green chairs, a brick chimney, and large windows showcasing the indoor space. A pathway leads to the entrance, framed by manicured landscaping.

Home in Palo Alto

Large Home in Palo Alto, 5 bedrooms, Pool

This large 5 bedroom and 3 bath home in Palo Alto has plenty of room for big groups and families. The home features 1 king bed, 3 Queen beds, 2 twin beds and a Queen pull-out sofa sleeper. The kitchen is beautiful and well equipped and this large home has plenty of room for everyone to relax. Enjoy the manicured backyard with large deck, BBQ and sparkling pool (w/child safety fence; pool/hot tub not heated). Close to Levi's Stadium, Stanford and downtown Palo Alto.

4.92 out of 5 average rating, 123 reviews

Superhost

The living area features a light-colored sectional sofa adorned with cushions, complemented by a wooden coffee table. A desk and office chair are positioned against the wall, while shelves display decorative items and books. Natural light brightens the space through recessed lighting.

Apartment in Redwood City

King bed Silicon Valley haven w/ pool and parking!

Beautiful and spacious apartment with everything you need: - Ultra-fast fiber optic internet - King bed main bedroom with en-suite bathroom - Free reserved covered parking - Fully stocked kitchen including complimentary coffee/tea/cocoa and cooking essentials - Washer/Dryer In-Unit - Gas Fireplace in Living Room - Ceiling Fans in Dining Area - Modern Appliances & Dishwasher - Sonic Internet Service with speeds up to 10 GB - Large Private Balcony - Pets Welcome

4.85 out of 5 average rating, 66 reviews

Guest favorite

Apartment in Belmont

Peaceful Family Friendly Entire 2BR/2BA Apt Unit

Peaceful Family-Friendly retreat in the Belmont hills - Spacious, Quiet, Yet Conveniently Located as a corner unit. This large 2BR, 2BA Entire Apartment is set in a Low-Traffic residential community surrounded by Parks, Hiking Trails, and Nature. 14 minutes from San Francisco International Airport (SFO); minutes from Belmont Downtown and Caltrain, with easy access to Silicon Valley. Convenient to Stanford University and Levi’s Stadium for visits and events.

5.0 out of 5 average rating, 7 reviews

Guest favorite

An inviting living area features a brick fireplace as its focal point, surrounded by a cozy sectional couch and a sleek entertainment unit with a large television. Natural light filters through multiple sliding glass doors that lead to a fenced backyard.

Home in Redwood City

Your spacious home in Silicon Valley (2bd/2ba)

Relax in a spacious and bright 2 bedroom/2 bath home. Beat the heat - A/C and pool! Queen bed in each bedroom. Well appointed kitchen. washer/dryer, WIFI, Netflix and Amazon Prime, small fenced backyard, HOA pool (seasonal) and green space (great for dogs). 40 minutes to San Francisco. Great location to experience all the Bay Area has to offer! *NOTE* This is my primary home that I am renting out while on vacation. It will have my things in it.

4.93 out of 5 average rating, 27 reviews

Top guest favorite

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

Luxury Silicon Valley Wellness and Work Oasis

Ideal for 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.

4.94 out of 5 average rating, 452 reviews

Guest favorite

A resort-style pool surrounded by lounge chairs is visible, with modern apartment buildings framing the scene. The area is bright and airy, showcasing a leisure space ideal for relaxation, with neatly landscaped greenery along the pool's edge.

Apartment in Menlo Park

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.

4.94 out of 5 average rating, 178 reviews