Vacation rentals with outdoor seating in Cupertino

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Top-rated outdoor seating rentals in Cupertino

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Guest favorite

Guest suite in Pescadero

4.99 out of 5 average rating, 148 reviews

Night & Day Cabin, a National Park like experience

Night and Day Cabin is located within a gated conservation community in the Coastal Redwood Forest of Pescadero, California. Originally deemed “Little Yosemite” this one-of-a-kind neighborhood inspired us to create a sanctuary to escape and create, to immerse ourselves with nature and connect with each other. Enjoy a private studio with full amenities: kitchen, bathroom, sleeper sofa, queen bed, and outdoor porch with fire pit. Everything you need to relax or adventure. Perfect for two adults.

Guest favorite

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

4.93 out of 5 average rating, 387 reviews

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Top guest favorite

The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 443 reviews

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.

Top guest favorite

A shared outdoor patio features a comfortable seating arrangement with modern chairs and a circular coffee table. An outdoor kitchen with barstools overlooks the space, while lush greenery adds to the ambiance. A gas fireplace stands as a focal point, enhancing the inviting outdoor setting.

Home in San Jose

4.98 out of 5 average rating, 239 reviews

Contemporary open floor plan home near Santana Row

Centrally-located single family home in West San Jose. Well maintained shared backyard with gas fireplace for your enjoyment. 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 quite neighborhood, so you get the best of both worlds. Minutes from SJ Airport, downtown SJ and Campbell, numerous high tech companies and world class eateries. 4th bed is sofa bed. **NO EVENTS or PARTIES** **NO SMOKING ON PROPERTY**

Top guest favorite

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

4.92 out of 5 average rating, 209 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.

Guest favorite

Apartment in San Jose

4.86 out of 5 average rating, 123 reviews

1B1B Top Floor | Downtown | Convention Cntr 403 Ji

Welcome to your cozy retreat in the heart of Silicon Valley! This stylish 1-bedroom apartment is ideal for business travelers, medical professionals on the go, couples, solo adventurers, and interns. ✔ Very close to SJ Airport, SF Convention Center, SAP Center, SJ Downtown... ✔ Self-Check in with code ✔ Free private on-site parking spot in the gated garage ✔ Central A/C and heater ✔ In-unit washer and dryer ✔ High-Speed Wifi ✔ Comfortable King-size bed ✔ Elevator in the building

Guest favorite

Loft in Hensley

4.92 out of 5 average rating, 141 reviews

Lovely Downtown Modern New-Build, w/Secure Parking

Our lovingly designed cozy but SMALL studio is perfect for solo travelers or couples. Modern design, upscale European stone/tile work in kitchen and bath. Private patio, parking w/ secure gate, laundry, electric fireplace, rainfall shower, LED vanity mirror, Keurig, desk, strong Wi-Fi, fully stocked kitchen w/ utensils and cookware. close to SJC Airport, SJSU campus, SAP Center, Convention Center, Downtown SJ, HWY-87, tech companies like Zoom, Adobe, PWC, EY. Walk to Japantown.

Top guest favorite

A colorful tiny home is seen surrounded by tall redwood trees. The exterior showcases vibrant blue and yellow walls, contrasted by natural wood planters filled with greenery. Sunlight filters through the trees, enhancing the inviting outdoor space.

Tiny home in Boulder Creek

4.96 out of 5 average rating, 189 reviews

Custom Cabin Retreat in the Redwoods

This retreat offers guests a unique experience of living in a well designed, minimalist space while having all one really needs. From the nautically-inspired curved ceiling w/ skylights to the custom redwood trim, this cozy retreat will inspire. Relax on the private deck with the fire pit, walk to the river or enjoy the local trails thru the towering redwoods. Santa Cruz beaches are just 35 min away, 25 min to Big Basin and Henry Cowell, and 35 min to fine dining in Saratoga.

Guest favorite

A solid-wood queen-size bed is dressed in a navy blue coverlet, featuring plush pillows. A Hello Kitty plush toy adorns the bed, complemented by a decorative striped pillow. The room is illuminated by warm light, enhancing the cozy ambiance.

Guest suite in San Jose

4.96 out of 5 average rating, 196 reviews

San Jose studio with laundry

This elegant, cozy studio is built with private entrance. It features with a solid wood queen-size bed, private bathroom, TV, private washer/dryer, private patio and reserved driveway parking for our guest. This studio is close to San Jose airport, Downtown, Levi’s Stadium, SJSU, Stanford, Valley Fair and Silicon Valley offices. It is also close to major freeways, 101, 680 and 880, very convenient for working in Silicon Valley and perfect for a relaxing getaway!

Top guest favorite

Guesthouse in Hensley

4.98 out of 5 average rating, 225 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 favorite

An outdoor patio area is equipped with a round table and several chairs positioned under an umbrella. A modern guesthouse is visible in the background, featuring large windows and a sliding door. Minimal landscaping, including grass and decorative plants, is present.

Guesthouse in Downtown San Jose

4.99 out of 5 average rating, 119 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 favorite

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, 280 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.