Holiday rentals with outdoor seating in Cupertino

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Cupertino

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming green guesthouse is nestled among towering redwood trees. The structure features multiple windows that bring in natural light, enhancing the connection with the surrounding forest. Sunlight filters through the branches, creating a serene outdoor atmosphere.
Cabin in Los Gatos
4.99 out of 5 average rating, 1,022 reviews

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Top Guest favourite
The spacious kitchen features an expansive island with four bar stools, allowing for casual dining. Light wood flooring complements the bright cabinetry and stainless-steel appliances. A view of the open living area is visible in the background, promoting a welcoming atmosphere.
Home in Santa Clara
4.93 out of 5 average rating, 206 reviews

4B/2.5B / Office Space / Open Plan / Huge Backyard

5 min drive (20 walk) to SCU / 10 min drive to Levi's Stadium / 15 min to Downtown San Jose + San José International Airport ✈ ☞ 4 Bedrooms, one of them is an office/bdr combo with a bed for a child or not very tall adult ☞ Huge Backyard w/ patio + BBQ + dining, great for children and pets ☞ Memory foam mattresses, 3 smart TVs ☞ Master suite w/ king + bathroom + smart TV ☞ Fully equipped + stocked kitchen ☞ Walking score 80 ☞ Free Parking in the driveway (2 cars), plenty free street parking

Top Guest favourite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.94 out of 5 average rating, 437 reviews

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.

Guest favourite
A comfortable sleeping area is presented with a spacious bed featuring white linens and a yellow accent pillow. Wall art depicting serene landscapes is displayed above the bed. A small kitchenette with a microwave and coffee bar is located in the corner, adding functionality to the space.
Guest suite in Sunnyvale
4.91 out of 5 average rating, 233 reviews

Luxurious Private Suite in Heart of Silicon Valley

Upscale, private suite w/separate entrance in quiet, safe neighborhood at the center of Silicon Valley! Minutes away from Apple/high tech companies, a cosmopolitan downtown, trendy restaurants, bars, and a historic park for leisurely stroll. Few blocks to US-101, Central Expy, and public transit. Enjoy the warm decor, comfortable queen Beautyrest mattress, luxurious sheets, stalked up coffee bar, private patio overlooking a peaceful back yard as well as unlimited free street parking.

Top Guest favourite
A spacious backyard is showcased, featuring lounge chairs arranged on manicured grass. A modern guesthouse with large windows and a bar area is set against lush greenery. Pathways of stone slabs lead to various outdoor seating areas beneath umbrellas, enhancing the space's inviting quality.
Guesthouse in San Jose
5 out of 5 average rating, 217 reviews

Stylish standalone guesthouse near Santana Rowing

Enjoy a stylish experience at this centrally-located guest house in West SJ. Modern finishes and well maintained backyard with gas fireplace for your enjoyment. Queen day bed with pull out twin trundle underneath to sleep up to 3 people. About a 10 minute walk to Santana Row and Valley Fair Mall. Enjoy the booming night life at Santana Row and come back to sleep in a quiet neighborhood. Minutes from SJ Airport, downtown SJ and Campbell, high tech companies and world class eateries.

Superhost
A bright living area is showcased with a red sofa adorned with yellow cushions, accompanied by an ottoman and a coffee table. Natural light filters through the large window with sheer curtains, illuminating the space. Barstools and a chic light fixture complement the open kitchen area.
Apartment in Sunnyvale
4.85 out of 5 average rating, 144 reviews

💎Cozy 1B1B in prime location • 🌲AC/1000m wifi/More

This newly renovated 1b/1b apartment welcomes you to a safe and convenient community in the heart of Silicon Valley, with clean & private room, garden-like backyard, individual AC, full kitchen, 1000Mbps mesh WiFi, 58 inch smart TV with free access to Disney+ & Hulu, dishwasher, and in-unit washer/dryer Shops, supermarkets, restaurants, public transport are all within walking distance. 5 mins to highway 101&280.😃 Close to tech companies like Go0gle, Apple, Amazon, Linkedin etc.🥳

Guest favourite
A serene bedroom is highlighted by a spacious bed with a padded headboard and soft bedding. Natural light pours in through sliding glass doors, revealing a private outdoor area. A bedside table with a lamp complements a white dresser against the wall.
Home in Santa Clara
4.93 out of 5 average rating, 147 reviews

M&J@Gorgeous remodeled 3B2B SFH/Bay Area | 2944

Gorgeous remodeled and furnished 3BR/2BA house which located in the heart of Silicon Valley and just minutes from downtown San Jose. Good landscaped garden makes you relax. * Equipped kitchen. * Fast WIFI, WFH friendly. * New & comfortable 3 queen beds which can sleep up to 6 people. * Central Heater / AC. * 65" smart TV (NO cable). * Safe and friendly neighborhood. * Easy access to expressways, 880, 280 & 101. * Many shops and excellent restaurants are within minutes.

Top Guest favourite
A modern living space features a light-colored love seat with two yellow accent pillows. A glass dining table is set with flowers, and a vibrant painting adorns the wall. Natural light enters through the front door, which is flanked by curtains.
Guest suite in Sunnyvale
4.98 out of 5 average rating, 229 reviews

Modern one bedroom in-law unit in Sunnyvale

Modern one bedroom in-law unit using high-end finishing with a comfortable queen bed, private bathroom, full kitchen, work-friendly desk, high speed wifi, cable TV, A/C heater combo and flower-lined side yard. Located in a safe and nice neighborhood. Perfect location for bay area traveller, with easy commute to all major high tech companies, walking distance to supermarket, restaurants and stores, and a short drive to Mountain View downtown and Caltrain station.

Top Guest favourite
A cozy living area features a stylish brown leather sofa and a round dining table accompanied by black chairs. Large glass doors invite natural light and provide views of the shared backyard. A modern kitchen is situated in the background, enhancing the open layout.
Guesthouse in Downtown San Jose
4.98 out of 5 average rating, 246 reviews

Private Abodu Guesthouse in Downtown San Jose

Stay at Flora's: Our Abodu guesthouse is the perfect spot for a solo traveler or a couple to stay in downtown San Jose. The Abodu has everything you need to feel at home. Enjoy our backyard or the great indoors at the end of your day. We offer really fast Wi-Fi, an easy to use coffee machine, and high quality linens for our guests' comfort. Our full kitchen includes high end appliances and everything you need to prepare your own meals.

Top Guest favourite
Large glass doors open to reveal a bright, open kitchen and living area. A modern design includes white cabinetry, stainless steel appliances, and a comfortable seating area with a light sofa. Natural light floods the space from a skylight above.
Guesthouse in Downtown San Jose
4.99 out of 5 average rating, 207 reviews

Quiet guesthouse near SJ airport with EV charger

Kick back and relax in this calm, stylish space. Brand new guesthouse build and landscape completed in 2023. Our guesthouse offers a full kitchen, WiFi, self check-in, FREE parking and washer and dryer. Tesla Universal EV charger Level 2 60 amp avilable for guest use. Centrally located in Downtown San Jose. A quick drive to the SJ airport, SAP Center, San Pedro Square, Levi’s Stadium, San Jose State University and Santa Clara University.

Top Guest favourite
A rustic caboose, painted in bright red, is nestled among lush green trees. Vintage machinery, featuring large wheels and a copper detail, is positioned nearby, surrounded by a gravel area. The ambiance is quietly rural, under the canopies of towering redwood trees.
Train in Cupertino
4.93 out of 5 average rating, 451 reviews

Caboose in the redwoods just outside of Cupertino

This rustic caboose is just 10 minutes from Cupertino and downtown Saratoga, perfect for both business travelers, outdoor adventurers, and everything in between. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else. Pets generally ok. Check with hosts. Pets must not be left alone.

Guest favourite
A well-lit living space features a comfortable sofa and a dining table set for two. The kitchen showcases modern appliances, including a stainless steel refrigerator and oven. Skylights enhance the airiness, while wooden cabinetry adds warmth. Sliding glass doors open to a secluded outdoor area.
Guesthouse in San Jose
4.98 out of 5 average rating, 293 reviews

Private cottage in the heart of Silicon Valley

Eden Cottage is our 686 square foot space in west San Jose. It is a custom built (in 2018) 1 Bedroom cottage with a private entrance, super fast WiFi, 50 inch flat screen TV, skylights, full kitchen, a bathroom with a huge shower plus a full sized washer and dryer pair. The cottage is entirely separate from our home and has a small yard and patio under a large oak tree that provides shade to the entire area.

Popular amenities for Cupertino outdoor seating rentals

When is the best time to visit Cupertino?

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Quick stats about holiday rentals with outdoor seating in Cupertino

  • Total holiday rentals

    Explore 60 holiday rentals in Cupertino

  • Nightly prices starting at

    Cupertino holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Cupertino holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cupertino rentals

  • 4.8 Average rating

    Cupertino stays are highly rated by guests—averaging 4.8 out of 5!

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