Special Edition

We’ve found 10+ unique staycations in San Jose. First, we want to talk to you about how you can support this free newsletter — and why your contribution matters.

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🏠 Home sweet home-away-from-home

Historic Hensley house. | Photo via Vrbo

Whether you’re looking to visit San Jose in style for the weekend or are a local in need of an unforgettable staycation, we’ve compiled a list featuring 13 extraordinary rentals in and around the great 408 that are worthy of a trip for you, your partner, the bestie, or the whole squad this year.

Just a heads up: Prices may vary depending on dates selected, taxes, and booking and cleaning fees (sorry, Airbnb and Vrbo make the rules, we just follow them).

Out-of-the-ordinary

Historic Hensley house master suite
This Victorian residence sits in a neighborhood that was established in 1865, and was adopted as a local Historical Landmark District in 1990.

~$110 a night
1 BD | 1 BA
Vintage light fixtures and furniture, outdoor patio, grand piano, spacious backyard

Private cabana
Located in downtown Willow Glen, this stay will transport you to a zen Bali rainforest.

~$265 a night
1 BD | 1 BA
In-room sauna, fully-fenced and private backyard with a pool, hot tub, outdoor furniture

For large groups

Luxury two-story single home
This home for up to 10 guests is perfect for a large family or friend retreat offering 2,000 sqft of modern facilities, spacious rooms, and nearby attractions.

~$310 a night
5 BD | 3 BA
Basketball half-court, deck and patio, small home gym, pool table, in-unit washer and dryer

Luxury

Modern smart home
This West San Jose stay is the ultimate Silicon Valley-esque home with the latest technology, newest appliances, and smart switches.

~$560 a night
3 BD | 2 BA
Swinging living room chairs, projector screen and Bose sound bar, hydro-massage bathtub, small in-home gym

9 more stunning spots

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