Vacation rentals with a pool in Hillsborough

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hillsborough

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

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Top guest favorite

Home in Mountain View

4.9 out of 5 average rating, 152 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!

Top guest favorite

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 422 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.

Top guest favorite

Guesthouse in Oakland

4.97 out of 5 average rating, 237 reviews

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

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

4.79 out of 5 average rating, 201 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, 201 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.

Top guest favorite

Guest suite in Willow Glen

4.95 out of 5 average rating, 141 reviews

Private Queen Suite-Pool & Hot Tub, private entry

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, 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. Hot tub and Pool are a perfect way to relax and end the evening.

Superhost

Home in Ben Lomond

4.95 out of 5 average rating, 111 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

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 569 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 Fairfax

4.95 out of 5 average rating, 196 reviews

Mountain View Retreat

Exclusive garden level retreat in the peaceful coastal hills of Marin County. Private entry French doors open to expansive decks, magnificent views, large infinity pool, hot tub, & gas barbecue grill. 2 Flat-screen cable TV's, with premium channels, (living room & bedroom). High-speed Wi-Fi internet throughout. Central location for easy access to San Francisco, Sonoma/Napa wine country, Pacific Coast beaches, spectacular Redwood forests, and endless miles of hiking & biking trails.

Superhost

Guest suite in East San Jose

4.86 out of 5 average rating, 725 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

Our home is on 1/2 acre hilltop lot, in a secluded, very quiet 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.

Top guest favorite

Home in El Sobrante

4.99 out of 5 average rating, 206 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

Superhost

Home in San Jose

4.81 out of 5 average rating, 318 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.