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

4.93 out of 5 average rating, 172 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.

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

4.99 out of 5 average rating, 345 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.

Guest favorite

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, 184 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!

Guest favorite

A serene outdoor pool area is surrounded by lush hills under a partially cloudy sky. The pool features calm waters reflecting the evening light, while a hot tub is positioned at one end. Distant hills offer a scenic backdrop to the setting.

Guesthouse in Emerald Hills

5 out of 5 average rating, 20 reviews

Casita Luna- Pool house 19 mins to Stanford

Please message via inquiry prior to booking. 🤠 The view is truly unbelievable- sunsets on the western hills; water & city light views sparkle all day & night. Country resort like setting adjacent to hiking trails, & cyclist paradise. Rustic organic ranch like property with a chic, polished interior. For couples or single occupancy. 5 Mins to 280/ Woodside, 10 mins to RWC. We ❤️ diversity and LGBTQIA friendly. No occupancy tax for stays of 31 days or more. Listing for registered guests only.

Superhost

A sunlit villa displays a charming white exterior with terracotta roof tiles. Two distinct chimneys rise above, while a balcony adds character. Surrounding oak trees provide a natural backdrop, contributing to a serene atmosphere, with gentle hills visible in the distance.

Villa in Woodside

5 out of 5 average rating, 3 reviews

Camellia Cottage with Pool View

Reminiscent of a 1920's Hollywood villa, enjoy the aesthetics of that romantic age, yet experience 5 star luxury pampering & the most modern of comforts. Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer, a tropical conservatory, perfect pool and infinity edge spa. Close to Woodside downtown, Highway 280, Silicon Valley, Sand Hill VC firms, Stanford University and Hospital. A short drive to San Francisco. SFO and SJC are only 25 minutes away.

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

4.89 out of 5 average rating, 465 reviews

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.

Guest favorite

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

4.95 out of 5 average rating, 20 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.

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

4.95 out of 5 average rating, 118 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.

Guest favorite

A spacious communal area features modern furnishings with a mix of light and dark tones. A circular dining table with soft, upholstered chairs centers the room, while a large television is mounted on a textured wall. Greenery adds a refreshing touch to the elegant design.

Apartment in Menlo Park

4.9 out of 5 average rating, 10 reviews

Zen Japan-inspired Suite - Resort hot tub/pool/gym

Step into tranquility with this beautifully designed Japanese-inspired studio, featuring traditional tatami flooring and a low Nectar king bed that offers a peaceful and restful sleep. This cozy space seamlessly blends the timeless elegance of Japanese minimalistic design with the convenience of modern amenities (hot tub, pool). Enjoy an oversized bathroom / shower, fully-equipped kitchen with modern GE appliances (Vitamix), making it perfect for both short stays and longer retreats.

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

4.91 out of 5 average rating, 103 reviews

Large Home in Palo Alto w/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). Located near Stanford, downtown Palo Alto, wonderful parks and restaurants.

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

4.94 out of 5 average rating, 406 reviews

Luxury Silicon Valley Work & Wellness Oasis

PLEASE CONTACT US FOR SUN–THU DISCOUNTS (2+ NIGHTS). Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve with private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Guest favorite

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

4.85 out of 5 average rating, 60 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