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

Condo in Mountain View

4.95 out of 5 average rating, 133 reviews

Spacious Top Floor Condo Retreat

Listen to the calming sounds of all the water features throughout the property from the secluded balcony. Inside, relax in 1000 square feet of upscale surroundings that include wood floors and high quality Tempur-Pedic king mattress. Later, head for the ground-floor pools and hot tub. 1000 sq ft of space on the top floor. Queen size adjustable firmness air mattress with clean beddings available upon request to be set up in the living room. You will be able to access the entire unit, 2 Swimming pools, and the hot tub. I will be available by text, phone or email throughout the stay. The quiet and beautiful setting is surrounded by trees. Within walking distance to CalTrain station, San Antonio shopping center, and Whole Foods, Trader Joe, movie theater plus numerous boutiques. Major tech companies located nearby include G00gle and Faceb00k. Stanford University is within a 10 minute drive. A short 5-10 minute walk to the Cal Train stop but the unit is not impacted by any train noise. The bus stop is conveniently around the corner to take you to Downtown Castro Street or Stanford University and beyond.

Top guest favorite

A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.

Home in Portola Valley

4.93 out of 5 average rating, 149 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

Guesthouse in Woodside

4.99 out of 5 average rating, 320 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 tranquil pool area is highlighted by a circular swimming pool surrounded by colorful blooming flowers. Two red lounge chairs are positioned beside the pool, inviting relaxation under the clear sky. Lush greenery and wooden fencing provide privacy, enhancing the outdoor setting.

Home in Mountain View

4.9 out of 5 average rating, 154 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 refreshing swimming pool is framed by lush greenery and bordered by a clean patio area. Two lounge chairs are positioned nearby, inviting relaxation. Sunlight reflects off the water, creating a calming atmosphere suitable for unwinding or enjoying time with family.

Home in Hayward

4.84 out of 5 average rating, 57 reviews

The Happy Hideaway - Pool, enjoyable backyard!

Welcome to my humble house. It's a modern contemporary house that you can enjoy your stay with your precious family. It's easy access to highway/San Mateo bridge, half hour to San Francisco, San Jose, Mountain View, and Palo Alto. Located in the middle of bay area! Last but not least, Restaurants are only 5-15 minutes away. NO Pets, and large gatherings outside registered guests. Be sure to follow and read the house rules to avoid confusion and extra fees. Thank you and see you soon!

Guest favorite

The outdoor space features a large, landscaped area with a serene pool reflecting surrounding greenery. A wooden table equipped with several chairs sits under a covered patio, illuminated by soft light from decorative lanterns. Lush plants and vibrant flowers enhance the tranquil atmosphere.

Guesthouse in Redwood City

4.97 out of 5 average rating, 32 reviews

Serenity in Silicon Valley: Eco-Friendly w Pool

Serenity Now, in Silicon Valley. New HONOMOBO 2BR/1BA shipping container home w/ full kitchen, billiards table that coverts to ping pong or a dining top, & access to a low-chemical heated pool. Situated in wooded area close to Stanford and Silicon Valley, all modern conveniences and access while nested in a serene, quiet location. Hiking trail nearby, off-leash for dogs. Friendly dog guests welcome. Fast internet. Natural products. No mold. No gatherings w/ those not staying. No parties.

Guest favorite

A well-maintained garden pathway leads to a pool area surrounded by lush greenery. Tropical plants and vibrant flowers add color to the landscape, while a variety of trees provide shade. The tranquil setting invites relaxation with the pool visible in the background.

Guest suite in Woodside

4.89 out of 5 average rating, 443 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.

Superhost

Guesthouse in Emerald Hills

4.78 out of 5 average rating, 36 reviews

A freestanding casita in a delightful grape garden

Escape to a secluded retreat featuring a queen bed plus spacious sectional sofa that can sleep another two, total four people. The ambiance of a wine country getaway with a sprawling yard, heated pool and rejuvenating spa. Enjoy the picturesque setting reminiscent of a lush vineyard. Shower bathroom. Kitchenette with two-hot plate, microwave, dishwasher, coffee maker, tea pot. Take advantage of the salt water pool, spa, and outdoor area exclusively available for your enjoyment.

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, 358 reviews

Silicon Valley Luxury I Sauna, Hot Tub, Pool

Secluded, peaceful 1,500 sq. ft. hillside escape for couples, nature lovers & business travelers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access & abundant wildlife. Features a fully equipped kitchen, pool table, fireplace, sauna, saline hot tub & heated pool (May–Oct). Fast fiber-optic WiFi for work & streaming. Prime location: I-280 (1.5 mi), Los Altos dining/shopping (3 mi), Mountain View (5 mi), Cupertino (8 mi), Palo Alto (9 mi).

Guest favorite

An indoor heated pool is surrounded by elegant tiled flooring featuring a floral pattern. Two lounge chairs are positioned nearby, and a large window provides natural light to the space. Lush greenery is included in the decor, adding a touch of tranquility.

Home in South San Francisco

4.91 out of 5 average rating, 70 reviews

Beautiful Entire Home | Bay Views | Private Pool

Welcome to Casa Blanca, your exclusive 4-bedroom retreat accommodating up to 12 guests. Enjoy breathtaking views of South San Francisco from the second balcony, take a plunge in the indoor heated pool. The entertainment options are endless with a pool table, foosball, and a private movie theater room. Our fully equipped kitchen, washer/dryer, and free Wi-Fi ensure a seamless stay. Book Casa Blanca for an unforgettable blend of luxury and entertainment!

Superhost

A private hot tub is situated on a wooden deck, surrounded by lush greenery and vibrant flowers. A cozy view of the adjacent house is visible in the background, framed by trees and scenic foliage.

Home in Brisbane

4.9 out of 5 average rating, 101 reviews

Luxurious Bayview Treehouse: Hot Tub, 15 min to SF

Immerse yourself in an architectural gem that balances modern elegance and rustic allure. Our four-bedroom, three-bathroom sanctuary is your secluded escape amidst expansive greenery, a canvas for unforgettable moments. Just 10 minutes from SFO Airport and 15 minutes from dynamic San Francisco, our home is your launchpad to exploration. The Bay Bridge graces the view from your private balcony and hot tub, framing your stay with an awe-inspiring vista.

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

4.97 out of 5 average rating, 146 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.