
Vacation rentals with a pool in Cupertino
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cupertino
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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 with high-speed Internet.

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.

Sanctuary in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, steampunk original art, state-of-the-art technology with a unique spa experience, providing the perfect private retreat. Surrounded by numerous hiking trails, many friendly animals, and vast wild forest all around us to explore to your liking, along with this exclusive unit serves to provide a refreshing, rejuvenating space to reconnect with your loved one, yourself and of course Mother Nature!

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.

Quiet Santana Row LUXE with Mt View
Quiet, luxurious loft on Santana Row. Recently remodeled. New LG WashTower. Sleep Number Bed. Full Kitchen w/ Nespresso, smart kettle, Vitamix Blender. Lululemon MIRROR. Theragun Mini. Best upscale dining & shops downstairs. Valley Fair Mall across the street. Underground parking. Security 24/7. 70 in TV. Electronic standing desk w/ Herman Miller Aeron Chair. Ideal for business/leisure. EXCLUSIVE select dining & shopping discounts Tesla Level 2 charging + Supercharging @ Winchester Garage

Cozy BUS on Farm Animal Rescue with CITY VIEW
Stay on a farm animal rescue in a 38’ yellow school bus conversion. If you are interested we also host an Airbnb Experience called Life With Farm Animals At Rancho Roben Rescues where you get a 90-120 minute up close encounter with all of the animals - taking time to learn about each of the unique creatures that lives here and the opportunity to interact with them directly. Pet a chicken, groom a pony, feed a goat, take a walk patrolling the fields with our livestock guardian dogs.

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.

Private Queen Suite-Pool & Hot Tub, private entry
This is your World Cup spot! Enjoy your private suite, bathroom and large smart TV with all the action. Located within a mile of eBay & Netflix plus downtown Los Gatos and Campbell. Great forLevi's Stadium 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center 4.6 miles. We have a professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

Modern 4bd/3ba w/ pool In Downtown MV
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 home with swimming pool is just minutes from Caltrain & light rail, Shoreline Lake, Stanford, Menlo Park, NASA & more! New HVAC installed Oct 2023. Step outside for a stroll and explore local and international cuisine, farmers market and shopping! Shared pool.

Luxury 2BR Apt near Tech Companies and Stanford
Welcome to our Luxurious 2 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, two comfortable bedrooms both with queen size bed, a pair of modern bathrooms, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

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, hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.

Private Oasis with Pool and Fire Pit
Escape to our private oasis where every detail is designed for your ultimate comfort. Indulge in a refreshing swim in our pool. Unwind and relax in our outdoor lounge area complete with a cozy firepit, perfect for savoring a glass of wine with your loved ones. Whether it’s a family retreat, a couples getaway or a work gathering, your ideal stay begins here! ** We do not offer pool heating **
Popular amenities for Cupertino rentals with a pool
House rentals with a pool

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Nuby's Bed & Breakfast (SCC Permit #251085)
Condo rentals with a pool

Sweet home near Apple 2 bedrooms, 1 queen, 1 twin

Luxury 2BR Condo Near Levi’s Stadium

Entire Condo - comfy and central

Modern 1B1B condo + quiet patio | Downtown Mt View

Contemporary 2BR - Blocks from Stanford Campus

Luxe 2Bed/2Bath w/ Parking, Fast WiFi, Pool & Gym

Close to Stanford! Walkable Silicon Valley Condo

Large two-bedroom two bath condo in Palo Alto
Other vacation rentals with a pool

Deluxe Studio near Kaiser SC:Traveler/Tesla intern

Sunol Chalet | 80 Acres • Pool • Gym • Game Room

Retromodern | Pool | Games | 2LV

Huckleberry Woods Sanctuary: Pool and Spa

Modern Retreat in the Heart of Silicon Valley

Guesthouse in woodside -

Spacious 4BR house | Beautiful Yard + Pool | A/C

Willow Glen Hideaway - Cottage with hot tub & pool
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ433 | ﺩ.ﺇ433 | ﺩ.ﺇ433 | ﺩ.ﺇ433 | ﺩ.ﺇ510 | ﺩ.ﺇ507 | ﺩ.ﺇ507 | ﺩ.ﺇ496 | ﺩ.ﺇ433 | ﺩ.ﺇ433 | ﺩ.ﺇ433 | ﺩ.ﺇ433 |
| Avg. temp | 10°C | 12°C | 13°C | 15°C | 17°C | 19°C | 20°C | 20°C | 20°C | 18°C | 13°C | 10°C |
Quick stats about vacation rentals with a pool in Cupertino

Total vacation rentals
Explore 110 vacation rentals in Cupertino

Nightly prices starting at
Cupertino vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 1,630 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Cupertino vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cupertino rentals

4.7 Average rating
Cupertino stays receive an average rating of 4.7 out of 5 from guests
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- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Oracle Park
- Monterey Bay Aquarium
- Capitola Beach
- Muir Woods National Monument
- Golden Gate Bridge
- Rio Del Mar Beach
- SAP Center
- Seacliff State Beach
- Twin Peaks
- Pier 39
- Henry Cowell Redwoods State Park
- University of California-Berkeley
- Montara Beach
- Palace of Fine Arts
- Levi's Stadium
- Winchester Mystery House
- California’S Great America
- Painted Ladies
- Davenport Beach
- San Francisco Zoo




