
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.ﺇ 220 per night before taxes and fees

Verified guest reviews
Over 1,830 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.

Private Queen Suite-Pool & Hot Tub, private entry
This is your Getaway spot! Enjoy your private suite, bathroom and large smart TV, pool and hot tub outside your door. Located within 3 miles of downtown Los Gatos and Campbell with great food options. Levi's Stadium/49ers 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.

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.

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.

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!

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.

Little Poolside House near Downtown. New AC!
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! New AC and heat. You will love this Bay Area getaway!

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!

Views for Miles | Hot Tub | Gated Hilltop Home
Retreat above the city in this one-of-a-kind home and gaze at the sweeping view of Silicon Valley. Rancho Ruby is a revived 1950s ranch designed with a modern California style. Every amenity and detail has been thoughtfully considered for the tech-savvy travelers. The home is open, peaceful, and cool. It sits on a hilltop, situated on a secluded & gated third acre lot to allow tranquility for guests but is only a 15 minutes drive to the city center.

Luxury Silicon Valley Wellness and Work Oasis
Ideal for 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.

Charming 2BR Apartment near tech Giants & 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, 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.
Popular amenities for Cupertino rentals with a pool
House rentals with a pool

Modern Rustic Home With Private Pool

Beautiful Large 4BR Home with POOL

Large Home in Palo Alto, 5 bedrooms, Pool

Cozy 2BR w/ Patios, Prime Mountain View Location

San Jose Home with Pool, Hot Tub, + Game Room

Luxe 3BR Retreat with Pool & Hot Tub

$1.8M Luxe MeiCasa | 5min Levi | EV | Massage Beds

Quiet Foothills Escape with Pool, Patio & BBQ
Condo rentals with a pool

Modern 1B1B condo + quiet patio | Downtown Mt View

Townhouse/condo. Close to 2 downtowns & Stanford

Large two-bedroom two bath condo in Palo Alto

Willow Place

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

WFH from Penthouse with View and location!

Easy Access to Stanford! Walkable Condo

Charming 1 bedroom, 1 bath, 2 Story Condo.
Other vacation rentals with a pool

Separate entry room near Stanford

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

Cozy Suite+Pool by Santana Row, Silicon Valley Gem

Relaxing 3‑Room with yard Pool • Near Santana Row

Private cottage in orchard and vineyard setting

Luxury Stay in Silicon Valley | San Jose Downtown

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

Menlo Park 2bd @ Sandhill Rd nr Stanford
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 |
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- Stanford University
- Monterey Bay Aquarium
- Golden Gate Park
- Santa Cruz Beach
- Muir Woods National Monument
- Santa Cruz Beach Boardwalk
- Golden Gate Bridge
- Capitola Beach
- Oracle Park
- Moscone Center
- University of California-Berkeley
- SAP Center
- Levi's Stadium
- Henry Cowell Redwoods State Park
- Pier 39
- Rio Del Mar Beach
- Mission Dolores Park
- Chase Center
- University of California San Francisco
- California’S Great America
- Seacliff State Beach
- Palace of Fine Arts
- Rodeo Beach
- Painted Ladies





