Holiday 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 favourite

Cabin in Oakland

4.97 out of 5 average rating, 222 reviews

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

POOL HEATED MAY 1st! Stunning, detached cottage w/ higher end finishes. Endless views of mountains set on beautiful, peaceful, upscale property. Very close to regional parks for hiking. Quiet & set amongst over an acre of land with redwood, pine, & oak trees. Pool heated 81F May 1st-October 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (4000 sq ft) is shared with main house (small family of 4). Secured driveway gate.

Guest favourite

Guest house in Woodside

4.99 out of 5 average rating, 309 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 favourite

Home in Mountain View

4.91 out of 5 average rating, 138 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 favourite

Guest house in Stinson Beach

4.93 out of 5 average rating, 476 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 favourite

Guest house 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 favourite

Guest suite in Woodside

4.89 out of 5 average rating, 431 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 favourite

Guest suite in Willow Glen

4.95 out of 5 average rating, 134 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 favourite

Guest house in Walnut Creek

4.91 out of 5 average rating, 545 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 favourite

Guest suite in Walnut Creek

4.99 out of 5 average rating, 527 reviews

Garden Oasis Studio with Spa and Pool, Walnut Creek

Former Plus-rated unit. How about a rejuvenating get-away with pool and spa? Picture window overlooking tranquil garden. Sunbathe poolside and ease into a deluxe hot tub. Watch TV from a comfy bed before falling into a restful sleep. Complimentary beverage for 3 nights or more. Deep cleaned. Two separate units off same foyer; but no shared walls. Private door to Studio. Shared access to spa/pool (9am-11pm) for overnight guests only. 27 stairs outside, 3 inside. Host lives upstairs.

Guest favourite

Rental unit in Evergreen

4.98 out of 5 average rating, 246 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 favourite

Guest house in Almaden Valley

4.97 out of 5 average rating, 941 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 favourite

Guest house in Willow Glen

4.97 out of 5 average rating, 586 reviews

Cabana with Warm Watsu Pool

Our guests best describe it as: ‘Like luxury hotel meets Zen retreat meets Day Spa meets Bali rain forest meets mom and pop warm hospitality’. A private cabana close to shops and restaurants in downtown Willow Glen. You’ll love our place because of the tranquil setting, warm watsu pool, Finlandia sauna (currently open), hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.