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, 134 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, 155 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 tranquil pool area is surrounded by lush greenery and rustic wooden structures. The clear water reflects the trees and sunlight above. A wooden deck offers space for relaxation, while adjacent seating arrangements and a grill provide options for outdoor enjoyment.

Guesthouse in Woodside

4.99 out of 5 average rating, 330 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.

Top 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

4.89 out of 5 average rating, 161 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 spacious lounge area features a large, light blue sectional sofa arranged around a wooden coffee table. Eye-catching pendant lights hang from the ceiling, and large glass doors provide views of the outdoor space. A dining area with modern chairs is visible in the background.

Apartment in Mountain View

5 out of 5 average rating, 12 reviews

Luxury Top Floor Apartment

Kick back and relax in this calm, stylish space. Clean Scandinavian lines give the space a sense of calm in this private top floor apartment. Enjoy mountain views from the Juliette balcony right outside your bedroom. Head down to one of two pools or jacuzzies available to you and bask in the resort-style spaces at Landsby. Easy access to trains and buses invite you to explore the South Bay area. Once inspired, you can use one of many dedicated work spaces to be as productive as you need to be.

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

4.83 out of 5 average rating, 63 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

A sleek outdoor space is visible, featuring a low-chemical heated pool surrounded by landscaped areas. Modern lounge chairs are placed near the pool, complemented by greenery and large oak trees in the background. The setting merges natural beauty with contemporary design.

Guesthouse in Redwood City

4.95 out of 5 average rating, 37 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, 451 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

4.79 out of 5 average rating, 38 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.

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

5 out of 5 average rating, 3 reviews

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!

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

4.94 out of 5 average rating, 16 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.

Superhost

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

4.96 out of 5 average rating, 112 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.