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, 124 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.

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 306 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

Home in Mountain View

4.9 out of 5 average rating, 136 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

Guesthouse in Emerald Hills

5 out of 5 average rating, 15 reviews

Stunning View Resort like pool house near 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.

Guest favorite

Rental unit in Menlo Park

5 out of 5 average rating, 20 reviews

Menlo Park 2bd @ Sandhill nr Stanford - Pool, Gym

Welcome to this beautifully designed 2 bedroom 2 bath home with everything you need, including surprise and delight details throughout. Located right off Sand Hill Road and just over a mile from Stanford University, Stanford Medical Hospital, and Stanford Shopping Center. Just beyond is Caltrain and Downtown Palo Alto. Enjoy amenities like our year-round heated pool, hot-tub, and fitness center. This ground-floor unit has a private patio perfect for lounging and enjoying California weather.

Guest favorite

Guesthouse in Redwood City

4.96 out of 5 average rating, 24 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

Guest suite in Woodside

4.89 out of 5 average rating, 430 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

Home in Ben Lomond

4.95 out of 5 average rating, 105 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

Guest suite in Half Moon Bay

4.86 out of 5 average rating, 71 reviews

A Half Moon Bay Getaway

Just a couple blocks from the coastal trail, the ocean, and a wonderful park, this unit is a great Half Moon Bay getaway. Be ready to hear the waves crashing at night or take a walk to Francis State Beach, Poplar Beach, or downtown Half Moon Bay. Start your day with a cup of coffee or tea or end the day with a glass of wine in your own relaxing coastside space. The unit is in a fenced in backyard space with shared access to a hot tub/lap pool and a firepit.

Guest favorite

Home in South San Francisco

4.96 out of 5 average rating, 56 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!

Guest favorite

Rental unit in Menlo Park

4.97 out of 5 average rating, 132 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.

Guest favorite

Guest suite in Ben Lomond

5 out of 5 average rating, 11 reviews

Peaceful Getaway Near Redwoods

Enjoy a tranquil stay among redwoods, a lush garden, and a sunny pool patio. This newly renovated private space is perfect for relaxation. Swim in the pool, visit Felton Covered Bridge, ride vintage trains at Roaring Camp, and find peace at Henry Cowell Park. Nearby Santa Cruz offers diverse dining and entertainment for a memorable blend of family activities and exploration!