Vacation rentals with a pool in San Mateo

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Mateo

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Mountain View

4.9 out of 5 average rating, 148 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 Monte Sereno

4.98 out of 5 average rating, 419 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Guest favorite

Cabin in Oakland

4.97 out of 5 average rating, 232 reviews

Spa style cottage! Jacuzzi, Sauna, Pool, Views!

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated 82F May 1st-Oct. 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Superhost

Home in Willow Glen

4.81 out of 5 average rating, 197 reviews

Beautiful Large 4BR Home with POOL

Need a vacation or a great place to stay in the Bay area in San Jose? Look no further as you'll love this "Resort" style, very spacious 4 BR home with large in-ground pool- beautifully remodeled and furnished with plush furniture, art deco, comfy beds, upgraded modern amenities and beautiful landscaped garden. Family and business friendly. Conveniently located minutes to downtown San Jose, Trains, Malls, SAP & Levi's Stadium, SCU, SJSU and SJC. Highways 87-280-101. Book your escape today!

Superhost

Villa in San Rafael

4.89 out of 5 average rating, 196 reviews

Waterfront Marin Retreat with Pool & Hot Tub

5,000 sq ft waterfront luxury villa right at the edge of the canal with private access to the water. Enjoy the heated pool and hot tub, or grab the kayak or paddle board and get on the water from your own dock. The home is 20 mins from San Francisco and Sonoma, has easy access to the 101 freeway, and close to China Camp State Park for hiking or downtown San Rafael. The five bedrooms are perfect for retreats, family vacations, or company off-sites. The spa-like environment is a true getaway.

Guest favorite

Guest suite in Willow Glen

4.95 out of 5 average rating, 137 reviews

Private Queen Suite-Private Entry, Pool & Hot Tub

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Campbell and Willow Glen. Great for Mountain Winery Concerts, 49ers/Levi's Stadium and SJC. We have a professional cleaning crew, so just relax and enjoy. Check-out like a hotel, no starting laundry!You will enjoy a well designed private room with queen bed, private entrance and connected private bathroom in our serene and safe neighborhood. Very high speed internet is included.

Guest favorite

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 564 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland, 50 mile from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers.

Guest favorite

Home in San Jose

4.86 out of 5 average rating, 125 reviews

Beautiful 3BD Home w/ Heated Pool and Fire Pit

Welcome to your next getaway! Corporate housing, business travelers, and families welcome. Work, relax and unwind in our beautiful and spacious home. Enjoy our pool with outdoor fire pit and BBQ grill (propane not included) and dining table. Hang out with the whole team or family and enjoy a delicious meal with your favorite glass of wine while admiring the beautiful lush scenery. ** Hot tub is non operational! Pool can be heated but will incur a fee - 24hr noticed needed !! **

Guest favorite

Home in El Sobrante

4.99 out of 5 average rating, 203 reviews

Zen Meets Pool Retreat!

Welcome to your peaceful get-away! Just minutes off both hwy 80 and hwy 24 and BART, you will find this quiet nook waiting for you to enjoy private outdoor living, complete with pool and hot tub, pool side seating with umbrellas and fire pit, patio with grill and of course, all the modern amenities inside to ensure a quiet and decompressing time away from it all! Have a fun sneak preview on youtube by entering the following search: Airbnb 100 Reviews Zen Meets Pool Retreat

Guest favorite

Apartment in Evergreen

4.98 out of 5 average rating, 253 reviews

Apartment above the valley.

This 2 bedroom apartment. It has outside stairs that lead up to a large private deck (with with spectacular view of Silicon Valley). The entrance is via sliding door from the deck. There are two bedrooms, one bathroom and a combined full kitchen/living room. The ground level pool and patio are shared space with owners. Living room has couch, TV, and Roku streaming. Apartment has good WiFi. Sit on the private deck and you may see wild turkeys, deer, and even a cow!

Superhost

Home in San Jose

4.81 out of 5 average rating, 313 reviews

Bay Area getaway w/ Pool + Heated Spa + EV charger

Spacious Victorian with POOL and EV Charger. 1/2 mile from downtown San Jose and close to airport. 4 bed/ 3 bath home with incredible backyard, equipped with 1/4 basketball court and gas firepit. Whole Foods, Coffee Shops and Breweries in walking distance! We have a movie style projector with Apple TV, Netflix and more! Full laundry room with washer and dryer. Our house is pet friendly, supplied with dog leash, pet bowls and several parks in walking distance.

Guest favorite

Villa in San Rafael

4.92 out of 5 average rating, 250 reviews

Tranquil Waterfront Haven

Explore profound relaxation or supercharged team building relaxation at this 4 bedroom haven with an authentic Finnish sauna with canal views, jacuzzi consciousness, paddle board, a kayak, and replete comfy zones to lazily exchange conversation. The tranquility of the canal will replace all Debbie downer thoughts with a symphony of luminous relaxation, bound to bedazzle wary minds and hearts. Guests will have the full first floor of the house.