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 15 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).
🏙️ Downtown
Victorian bungalow
Built in 1906, this newly-remodeled home keeps its history with vintage-inspired artwork — while also staying trendy.
- ~$200 a night
- 2 BD | 1.5 BA
- Large kitchen with island, in-unit washer and dryer, private patio
Large, stylish home
Bring a crew of up to 14 at this bright, modern home situated in a peaceful neighborhood next to Watson Park.
- ~$450 a night
- 5 BD | 3 BA
- Jetted tub, updated kitchen appliances, conveniently located near San Jose Mineta International Airport
Private Abodu guesthouse
This airy guesthouse is suited for a solo traveler or couple looking for a serene getaway.
- ~$160 a night
- 1 BD | 1 BA
- Long-term stays allowed, shared backyard with outdoor furniture, in-unit washer and dryer
🧸 Family-friendly
Spacious modern home
Take a family retreat at this contemporary home within Willow Glen, complete with large gathering spaces, games, and a billiard room.
- ~$186 a night
- 3 BD | 2 BA
- Sun room with pool table and elliptical machine, electric fireplace, spacious backyard, in-unit washer and dryer
Cozy home away from home
Located near Apple Park in Santa Clara, this home offers bunk beds for the kids, a private front yard, and many shopping and entertainment attractions nearby.
- ~$195 a night
- 3 BD | 2 BA
- Indoor fireplace, outdoor movie set up, spacious living room
Stylish home
There is fun for everyone at this chic, newly-remodeled home situated 10 minutes away from the San Jose Mineta International Airport.
- ~$495 a night
- 4 BD | 3 BA
- Bunk beds, half-basketball court, jungle gym, playground, outdoor furniture with fire pit
👀 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.
- ~$170 a night
- 1 BD | 1 BA
- In-room sauna, fully-fenced and private backyard with a pool, hot tub, outdoor furniture
Retro arcade escape
Bring a group of up to 16 back to the 1980s and 1990s with a retreat full of retro video games, VHS movies, arcade machines, and more.
- ~$514 a night
- 8 BD | 4 BA
- Video game den, spacious backyard with outdoor furniture, a grill, and cornhole
👥 For large groups
Newly-remodeled luxury home
Entertain a group of up to eight in this open-space layout stay that features a kitchen with a large island and a spacious L-shaped couch.
- ~$410 a night
- 4 BD | 2 BA
- Single beds for four people, newly-remodeled bathrooms, large dining table, and garage yoga set-up
Luxury two-story single home
This 10-guest house is perfect for a large family or friend retreat offering 2,000 sqft of modern facilities, spacious rooms, and nearby attractions.
- ~$299 a night
- 5 BD | 3 BA
- Basketball half-court, deck and patio, small home gym, pool table, in-unit washer and dryer
Spacious getaway home
Located five minutes away from Santana Row, this stay offers great outdoor space for entertaining, as well as new furniture + premium mattresses.
- ~$277 a night
- 3 BD | 2 BA
- Full kitchen, outdoor patio with fire pit, pool, and ping pong table
✨ 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.
- ~$440 a night
- 3 BD | 2 BA
- Swinging living room chairs, projector screen and Bose sound bar, hydro-massage bathtub, small in-home gym
Minimalist luxury home
Enjoy the vacation vibes of this home, with its cozy but trendy furniture and natural light.
- ~$564 a night
- 3 BD | 2 BA
- Bunk beds, free parking, two minutes away from Westfield Valley Fair, full kitchen
Santa Cruz mountains retreat
Surround yourself with redwood trees and venture further into this stay 15 minutes away from Los Gatos, and 25 minutes away from Santa Cruz.
- ~$425 a night
- 3 BD | 3 BA
- Outdoor deck with hot tub and fire pit, in-home gym, large living room, games
