
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.

3 BR Home on Vineyard nr Palo Alto & Stanford
Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

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.

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.

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.

Apartment above Levi Stadium.
18 miles from Levi Stadium! Your Superbowl HQ Take tram to stadium and avoid traffic JAM and parking nightmare! This 2 bedroom apartment. With with spectacular view of Silicon Valley and Levi Stadium). There are two bedrooms, one bathroom and a combined full kitchen/living room. 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! The Rental fee includes the Santa Clara Short Term Rental Tax!

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.

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.

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 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!

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.
Popular amenities for Cupertino rentals with a pool
House rentals with a pool

Beautiful Large 4BR Home with POOL

Large Home in Palo Alto, 5 bedrooms, Pool

Stunning Group Retreat w/Pool!

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

Modern Retreat in the Heart of Silicon Valley

Luxury 4-Suite Carbon-Neutral Home With Pool

Resort Style Retreat -Private Pool, Hot Tub & View

Starbird Oasis: Pet Friendly with Private Pool!
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.

San Jose Charming Home in the Heart of Bay Area

Luxury Condo Minutes to Levi’s Stadium & World Cup

Modern 1B1B condo + quiet patio | Downtown Mt View

Contemporary 2BR - Blocks from Stanford Campus

Pool Access! Base to See Stanford & Int’l Soccer
Other vacation rentals with a pool

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

Private cottage in orchard and vineyard setting

Stay Alpha Home • Modern Redwood Retreat with Pool

Relaxing 3‑Room with yard Pool • Near Santana Row

Cozy Suite+Pool by Santana Row, Silicon Valley Gem

Chic-Roomy 2Br 2Ba/Pool • Near Levis, Apple, Nvdia

Los Gatos Villa: hot tub, sauna, pool, and huge yard

Cute 1B1B Apartment near Levi’s Stadium SJ
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 544 | ﺩ.ﺇ 551 | ﺩ.ﺇ 463 | ﺩ.ﺇ 433 | ﺩ.ﺇ 510 | ﺩ.ﺇ 507 | ﺩ.ﺇ 507 | ﺩ.ﺇ 496 | ﺩ.ﺇ 433 | ﺩ.ﺇ 433 | ﺩ.ﺇ 433 | ﺩ.ﺇ 433 |
| 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.ﺇ 184 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
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- Stanford University
- Monterey Bay Aquarium
- Golden Gate Park
- Santa Cruz Beach
- Muir Woods National Monument
- Capitola Beach
- Oracle Park
- Moscone Center
- Golden Gate Bridge
- Santa Cruz Beach Boardwalk
- University of California-Berkeley
- Levi's Stadium
- SAP Center
- Henry Cowell Redwoods State Park
- Rio Del Mar Beach
- Mission Dolores Park
- Pier 39
- Seacliff State Beach
- California’S Great America
- Chase Center
- University of California San Francisco
- Palace of Fine Arts
- Montara Beach
- Rodeo Beach





