
Vacation rentals with a pool in Cupertino
Find and book unique homes with a pool on Airbnb
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.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 1,730 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
Top-rated rentals with a pool in Cupertino
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

The Alpaca House
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.

Snug and Cozy between the Skyline and the Sea
Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

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!

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!

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.

Luxury Silicon Valley Wellness and Work Oasis
Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

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.

Private Queen Suite-Pool & Hot Tub, private entry
This is your Getaway and World Cup spot! Enjoy your private suite, bathroom and large smart TV with all the action. Located within 3 miles of downtown Los Gatos and Campbell great food options. Levi's Stadium 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center/NCAA/Sharks 4.6 miles. We have professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

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.

Luxurious Ritz Suite w fireplace, Business retreat
All natural limestone allergen-free retreat, lush greenery, indoor/outdoor living. Very quiet, safe location, walk to conveniences, parks. Easy parking * Separate french door entrance * Self check-in & check-out with lockbox * Spacious suite with high ceilings * Gas fireplace * Kitchenette * Walk-in closet * Spa bathroom * Upgraded high speed WiFi * Aroma & sound therapy * Portable grill available

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

Beautiful Large 4BR Home with POOL

The Rose Garden Retreat: Premier Luxury Experience

Large Home in Palo Alto, 5 bedrooms, Pool

Silicon Valley Executive home in Santa Clara

Retromodern | Pool | Games | 2LV

Luxury 4-Suite Carbon-Neutral Home With Pool

3 BR Home on Vineyard nr Palo Alto & Stanford

Modern Family Stay |Steps to Parks + DT Los Gatos
Condo rentals with a pool

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

Spacious 2BR/2BA w/ Patio + Hot Tub Access

Modern 2‑bed, 2‑bath top‑floor apartment.

Luxury Condo Minutes to Levi’s Stadium & World Cup

Modern 1B1B condo + quiet patio | Downtown Mt View

1BR/1BA Near Santana Row | Work-Friendly + Parking

Shop, Hike & Sip Wine: Pleasanton Gem w/ Balcony!

Spacious, luxury condo in downtown San José, CA
Other vacation rentals with a pool

Kaiser| Great America| Free parking |Multizone A/C

Deluxe Studio near Kaiser SC:Traveler/Tesla intern

Luxe Apartment Downtown San Jose w/ Gym, Pool

Redwood Oasis - Private Heated Pool by State Park!

Huckleberry Woods Sanctuary: Pool and Spa

Modern Retreat in the Heart of Silicon Valley

2 BR/2 full bath Modern Santana Row Condo sleeps 6

Country Club Living on Golf Course & amazing views
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ544 | ﺩ.ﺇ551 | ﺩ.ﺇ463 | 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 |
Destinations to explore
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- Rentals with a patio Cupertino
- Rentals with a fireplace Cupertino
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- Rentals with a hot tub Cupertino
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- House rentals Cupertino
- Rentals with pools Santa Clara County
- Rentals with pools California
- Rentals with pools United States
- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Monterey Bay Aquarium
- Oracle Park
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
- Rio Del Mar Beach
- Santa Cruz Beach Boardwalk
- SAP Center
- Pier 39
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Seacliff State Beach
- Twin Peaks
- University of California-Berkeley
- Rodeo Beach
- Palace of Fine Arts
- Levi's Stadium
- Montara Beach
- Winchester Mystery House
- California’S Great America





