Vacation rentals with a pool in Cupertino

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Top-rated rentals with a pool in Cupertino

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

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Superhost

Guest suite in San Jose

4.88 out of 5 average rating, 644 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 solar thermal heated pool when weather permitted.

Jul 22 – 29

G$26,867 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 9 – 16

G$70,224 GYD per night

Guest favorite

Home in Mountain View

4.88 out of 5 average rating, 113 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!

Mar 2 – 9

G$31,040 GYD per night

Guest favorite

Guest suite in San Jose

4.94 out of 5 average rating, 109 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. We follow all cleaning guidelines to protect the health of all guests. 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.

Oct 8 – 15

G$30,638 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$33,903 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.

Oct 8 – 15

G$31,809 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 13 – 20

G$33,591 GYD per night

Guest favorite

Home in San Jose

4.8 out of 5 average rating, 279 reviews

Downtown Oasis with Heated Pool near Whole Foods

Spacious Victorian with POOL and SPA 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.

Oct 10 – 17

G$91,835 GYD per night

Guest favorite

Condo in Santa Clara

4.94 out of 5 average rating, 264 reviews

La Casa de Alpaca

Welcome to La Casa de Alpaca. Our home is located in the beautiful Rivermark community of Santa Clara. The space consists of 2 bed / 2 bath located on the top floor, with access to a pool, hot tub, gym, and yoga room. Local Destinations: Santa Clara Convention Center Great America Theme Park Downtown San Jose Levi's Stadium SAP Center Oracle Rivermark shopping area: restaurants and groceries AMC Mercado 20 Plaza: restaurants and movies We are business traveler ready.

Jan 14 – 21

G$44,922 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$38,758 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!

Jul 20 – 27

G$48,109 GYD per night

Guest favorite

Guesthouse in Monte Sereno

4.9 out of 5 average rating, 187 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Jan 7 – 14

G$38,585 GYD per night