Holiday 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 favourite

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

4.92 out of 5 average rating, 174 reviews

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.

LocationValueBathroom

Top Guest favourite

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

4.99 out of 5 average rating, 365 reviews

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.

LocationFamilyHeating

Superhost

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

4.88 out of 5 average rating, 192 reviews

Little Poolside House near Downtown Mountain View!

Absolutely the best location in Mountain View, steps from Downtown! Situated near all the entertainment, nightlife & attractions this vibrant city has to offer. This beautifully furnished little poolside house is just minutes from the Caltrain & light rail, Shoreline Lake, Stanford, Menlo Park, NASA Ames Center & more! Step outside for a stroll and explore local and international cuisine, wonderful farmers market and shopping! Perfect for family or friends, you will love this Bay Area getaway!

FamilyLocationDecor

Top Guest favourite

A spacious living area features a majestic stone fireplace as the focal point, framed by vaulted wooden ceilings. Elegant furniture, including a cozy sofa and armchairs, are arranged around a glass coffee table, while warm lighting from a chandelier adds to the inviting ambiance.

Home in Boulder Creek

4.96 out of 5 average rating, 25 reviews

Nuby's Bed & Breakfast (SCC Permit #251085)

Stay in an upscale place that’s near everything you want to visit. This beautiful estate nestled within the Redwood trees, is a 10 min walk to downtown Boulder Creek restaurants and markets. The home has one of the most majestic fireplaces w/vaulted wooden ceilings in Santa Cruz County. Every room has its own private bath. Jacuzzi, tub, swimming pool, front porch, deck, and firepit area. Most recently, the estate served as a filming location for Season 3 of a popular series on Amazon Prime.

FamilyValueGetting around

Guest favourite

A serene outdoor area features a solar-heated pool surrounded by lush greenery. Comfortable lounge chairs are positioned under a wooden pergola, offering a space for relaxation. The backdrop consists of rolling hills and trees, creating a peaceful natural setting.

Guest suite in Boulder Creek

4.93 out of 5 average rating, 82 reviews

Huckleberry Woods Sanctuary: Pool and Spa

Santa Cruz VR permit # 121241. Relax in the serenity of 2 acres in the heart of the redwood forest, plus lush gardens, gated for your security and privacy. A hot tub and direct solar heated pool is just outside your door, with no visible neighbors. It's just a short drive to Santa Cruz's famous beaches, restaurants, and family-friendly activities. We are hosts that live on the same large property, so we can provide local info and quick fixes. Come escape together into our magical forest.

ValueFamilyPool

Top Guest favourite

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

4.94 out of 5 average rating, 440 reviews

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, 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.

ValueFamilyGetting around

Top Guest favourite

A private entrance is highlighted by a covered porch with two comfortable chairs and a small table. A large planter stands next to the door, while lush greenery surrounds the area, creating a serene outdoor setting.

Cabin in Woodside

4.96 out of 5 average rating, 28 reviews

Guesthouse in woodside -

This private guest house is located on one of the most prestigious properties in Woodside with it's own private entrance & setting on a 1.5 acre lot. Includes living room, 1 queen bedroom, sofa bed, kitchen and private patio - * There are 15 stairs from where the car is parked to the guest house. Access to basketball court and play structure. No access to the pool/hot tub/fire pit. Close to restaurants, 2 mins from 280 HW, 3 mins to downtown Woodside, 10 mins to Stanford University.

LocationFamilyCleanliness

Guest favourite

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

4.95 out of 5 average rating, 121 reviews

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.

FamilyValueCheck-in

Guest favourite

A serene outdoor area showcases a sparkling saltwater pool surrounded by lush tropical landscaping. Sun loungers are positioned nearby, offering a relaxing spot for guests. A pool house can be seen in the background, framed by vibrant greenery under a clear blue sky.

Home in Menlo Park

4.9 out of 5 average rating, 60 reviews

Mission style, w. Pool, Hot tub, walk to downtown

Beautiful Spanish style and open concept home with aesthetically decorated inside and outside areas. The large well-groomed Mediterranean -inspired landscaping and backyard, saltwater pool, hottub, outdoor rain-shower, well-equipped outdoor BBQ kitchen & dining, large lounge seating areas, and fire pits. You'll immediately feel at home at this ideal place for a family- or business people who appreciate a beautiful setting for their stay close to Palo Alto, Stanford and much more.

FamilyValueCheck-in

Guest favourite

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

4.92 out of 5 average rating, 118 reviews

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.

ValueFamilyBathroom

Superhost

An aerial view captures the expansive outdoor area of the Anton Menlo Apartments. A resort-style pool is centrally located, surrounded by lounge chairs and shaded seating areas. Lush landscaping and modern architecture define the space, with additional amenities visible, including a community lounge.

Apartment in Menlo Park

4.93 out of 5 average rating, 175 reviews

Beautiful Spacious Living w/Resort Like Feel

Welcome to our lovely spacious studio apartment 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 fully furnished living area, queen comfortable bed, and a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals. Bedroom does not have a door, as this is a studio.

LocationValueParking

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

4.84 out of 5 average rating, 64 reviews

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

ValueFamilyAmenities