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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Guest favorite

Cabin in Oakland

4.97 out of 5 average rating, 185 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.

Nov 18 – 25

G$50,683 GYD per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 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.

Oct 2 – 9

G$70,171 GYD per night

Superhost

Guest suite in Los Altos Hills

4.8 out of 5 average rating, 148 reviews

A private hillside suite nestled among oaks

Better than the Four Seasons or the Rosewood! Beautiful, compact, private in-law suite in the walk out basement of our modern home. Enter via outdoor stairs from parking area to suite. Serene bay views and lush greenery below grand oaks. Your suite has a very comfortable King bed, Japanese washlet, closet space, TV, wi-fi, private washer/dryer, fully equipped kitchen with gas stove, microwave, fridge/freezer & dishwasher. Ceiling fan, radiant in-floor cooling/heating. Private parking. 280 SF.

Jul 8 – 15

G$33,878 GYD per night

Guest favorite

Guesthouse in Monte Sereno

4.97 out of 5 average rating, 387 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.

Sep 21 – 28

G$31,785 GYD per night

Guest favorite

Guest suite in Walnut Creek

4.99 out of 5 average rating, 534 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.

Aug 20 – 27

G$33,074 GYD per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 409 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.

Jul 23 – 30

G$33,293 GYD per night

Guest favorite

Home in Walnut Creek

4.97 out of 5 average rating, 227 reviews

Gated Home. Heated Pool. Top Location.

Fully remodeled gated home on exclusive private lane in the heart of Walnut Creek. 2000" ft, single story. Pool heated 365 days. Fully landscaped 1/2 acre Yard. Short walk to shops, restaurants, trails & famous Bancroft Gardens. Access 2 BART (train) stations, downtown Walnut Creek and freeways in minutes. Transparent pricing & 5 Star Amenities. No Guest Cleaning Tasks for check out. All Fees and Taxes included in nightly rate. *NO PARTIES OR EVENTS * STRICTLY ENFORCED *

Jan 19 – 26

G$75,480 GYD per night

Guest favorite

Apartment in San Jose

4.98 out of 5 average rating, 223 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!

Nov 23 – 30

G$38,728 GYD per night

Guest favorite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 862 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!

Jun 16 – 23

G$48,276 GYD per night

Guest favorite

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 502 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cosy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland. 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

Feb 22 – Mar 1

G$26,825 GYD per night

Superhost

Home in Burlingame

4.86 out of 5 average rating, 155 reviews

Cozy, Spacious Villa with Private Pool & Bay View!

Set back from an already quite, wide residential street, the closed in the courtyard like creates an added layer of privacy that permeates the entire property. As a single level home with all four bedrooms, clustered together at one end of the house, and one junior suite, two living rooms, a kitchen, and a dining room clustered at the other, this home feels very comfortable on a daily basis, but also very capable for entertaining when needed.

Aug 20 – 27

G$191,760 GYD per night

Guest favorite

Guesthouse in Belmont

4.88 out of 5 average rating, 213 reviews

Private Garden Cottage in Belmont Hills

A fully accessorized cottage in a private and quiet setting at the heart of the San Francisco Bay Area. Newly renovated backyard with always blooming flowers, fruit trees, hot tub, and pool. Regular visits from deer, and professional night illumination make this place feel like a magical forest getaway, quiet and secluded from the surrounding city. Enjoy the multitude of patios for reading and relaxation. We even have a tree house for the kids.

Sep 28 – Oct 5

G$60,286 GYD per night