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.

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Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 307 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

4.91 out of 5 average rating, 137 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 Stinson Beach

4.93 out of 5 average rating, 475 reviews

Romantic Creekside Cottage

Your cottage escape awaits! Set against the backdrop of the mountains and facing the Pacific, our lovely, romantic cottage is waiting for you to enjoy. Open your doors to the sounds of birdsong, ocean waves and cascading water. Watch the sunset from "The Kissing Bench" and sip your morning coffee in your patio. Light a fire and curl up with a book. When you are ready to step out, a few minutes down the path will bring you straight to town, the beach and the trails of Mt. Tamalpais.

Guest favorite

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 413 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

Guest suite in Walnut Creek

4.99 out of 5 average rating, 564 reviews

Garden Oasis Suite with Spa and Pool, Walnut Creek

How about a rejuvenating get-away with a pool and spa? Bask in the late afternoon sun on a patio lounger overlooking a serene pool and tropical garden. Enjoy an evening snack while watching a movie or enjoy a good read. Luxuriate in a deluxe spa before falling into a comfy bed. Keep your work area separate from the bedroom. Brand new split AC/heater! Deep cleaning. 2 Airbnb units off same foyer. 27 steps. Neighborhood annexed to Lafayette. $25/person for additional guests or early check-in.

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.

Guest favorite

Guest suite in Willow Glen

4.95 out of 5 average rating, 133 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, 539 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.

Superhost

Guest suite in East San Jose

4.87 out of 5 average rating, 695 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

Our home is on 1/2 acre hilltop lot, in a secluded, very quite cul-de-sac, with easy access to major freeways, minutes from SJC airport, downtown, SAP, SJSU, convention center. This listing is for an entire separate unit, attached to main house. It features 2 rooms with private yard and pool to yourself. You are free to relax in the back yard with view, surrounded by mature trees, hummingbirds, butterflies while surf the net, or swim in our private pool when weather permitted.

Guest favorite

Rental unit in Evergreen

4.98 out of 5 average rating, 245 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!

Guest favorite

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 940 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Guest favorite

Guesthouse in Sunnyvale

4.99 out of 5 average rating, 209 reviews

Lux Villa, sunny deck w fire pit, romantic retreat

• Indoor/outdoor living, private deck, outdoor seating • Has it's own air conditioning & heating units controlled by a Nest thermostat (no shared ducts) • Ventilated with an air filtration system • Eco cleaners and disinfected • Self check-in & check-out • Upgraded high speed WiFi • Gas fireplace • High ceilings • Gourmet kitchen • Aroma & sound therapy • Walk-in shower w/heated towel rack • Sunny private deck seating w fire pit