Villa holiday rentals in Silicon Valley

Lovely 4 bedroom gated Villa with free parking

Welcome to our beautiful luxury Villa. A lovely 4 bedroom 2 floor villa nestled in the beautiful hills of Los Gatos, located on 1.7 acres of gated land. Expansive decks on both floors with views, perfect for enjoying the propane fire pit & grill. Ideal for small retreats, corporate off sites & business travel. Just a 5-10 minute drive from downtown Los Gatos. Gym, retro arcade, billiards & foosball table included. Equipped with full washer & dryer, whole house LifeSource water filtration system.

Location · Family · Comfort

Private Terraced Garden Suite - #1 Favorite ★★★★★

Our #1 on Airbnb listing! Fully updated in 2026, this is a private, tranquil retreat within our larger 5-bedroom home. The suite is locked off from the rest of the house and has its own private entrance. Guests who love this suite include couples, solo adventurers, and business travelers. You reach the Terraced Garden Suite via a side entrance (you must be able to walk up a fairly steep incline) to the rear yard, then down a flight of stairs. We are close to groceries, freeway access, and BART.

Location · Family · Accuracy

Tesla EV Charger Basketball Pool Table Hot Tub Spa

Luxury Getaway at our Silicon Valley home w/3300+ SqFt of fun space. Spend less time waiting at charging station and more time enjoying your vacation! FREE Tesla /EV charger on site, hot tub spa, Basketball, pool table, & Foosball. 15 min to SFO Airport, 20 min to Stanford/San Francisco, 25 min drive to San Jose SJC. Newly furnished w/high quality touches and located in a safe neighborhood yet just 3 min from grocery and dinning. Perfect place to work & relax with easy access to 101/280 HWY.

Location · Family · Condition

Gather w/ Friends&Family in 5BR Getaway Villa!

Welcome to this spacious and dreamy Victorian villa filled with charming, modern elements. Located near Piedmont & Grand and close to San Francisco, it strikes the perfect balance between city and relaxation. Perfect for up to 16 guests, it spans across 3 floors and has 2 full kitchens, 3 living areas, 2 offices nooks and a tiki barn perfect for entertaining! ✔ Minutes to Attractions ✔ Three Floors ✔ 5BR/4BA ✔ Tiki Barn ✔ Backyard Dining/Patio *Note: There is no Air-Con in this property*

Value · Location · Long stay

Private hilltop 3-4 bd estate in Upper Rockridge

San Francisco from the heart of the East Bay's beautiful Upper Rockridge neighborhood. Full on view of San Francisco, the Golden Gate Bridge, Bay Bridge, Alcatraz surrounded my Mediterranian hillsides for you and your guests. The home is secluded but right in the middle of it all, amidst beautiful California oaks. Indoor/outdoor living, 4 bedrooms, 3 full baths, sleeps 6-8. Perfect for families, Centrally located for exploring the San Francisco Bay Area, Silicon Valley and Napa Valley.

Location · Family · Cleanliness

4 BR Luxury Home with Hot Tub near SF UC Berkeley

Villa Pearl is a gorgeous space for a perfect family reunion or a work retreat. It’s a haven for quality time with family or your beloved. The space has been featured in many film and ad campaigns, the gorgeous design is set to impress. ✔14 ft high ceiling ✔open entertainment space ✔Private hot tub in the private garden ✔garage parking + EV charging ✔3 mins drive to the Bay Bridge ✔10G fiber optic wifi ✔10 mins to Emeryville food & shopping ✔10 mins to Berkeley ✔25 mins to San Francisco

Family · Location · Comfort

Luxury French Chateau among rolling hills

Beautiful, private luxury home with 5 bedrooms/4 baths located on a little less than an acre in a stunning country setting. Stunning views of the hills from backyard and almost every room. The 5,000+ sq. ft house boasts an amazing kitchen, a formal living room, a family room, media room and a home office. It's set in a very peaceful & natural setting that you will fall in love with. The backyard is an oasis with a built-in BBQ, sitting and dinning areas to fully enjoy the outdoors!

Family · Value · Condition

5BR, 400sf Studio, Indoor Warm Pool, A/V, Gardens

A 5-bedroom urban retreat with intentional spaces for healing and recreation: - 400sf workshop/yoga/video studio - Custom indoor warm pool with unique audio-visual features. - Home theater, 100" screen, 2 pianos, video recording/broadcasting - Secluded backyard, waterfalls, gardens A wholesome artistic interior design. Fully equipped with appliances and amenities. Centrally located 30 minutes from downtown San Francisco, SF Airport, Silicon Valley, San Jose and Berkeley.

Family · Location · Pool

Family Retreat near South Bay and Santa Cruz Beach

Permit# 231447 Nestled in Boulder Creek's mountains, just 30 min from Santa Cruz beaches and 1 hr from the Bay Area. Wake up surrounded by ancient redwoods, explore 20+ nearby hiking trails, then unwind in the hot tub under the stars. Great WiFi and cell coverage—stay connected when you want, unplugged when you don't. Built for family reunions, friend getaways, and groups seeking nature without sacrificing comfort. Visit thecrowsnestretreat dot com for more info

Location · Family · Quiet

Warm 2BR/1BA house Silicon W/D parkin near SJ town

Gorgeous remodeled and furnished 2BR/1BA house which located in the heart of Silicon Valley and just minutes from downtown San Jose. *Equipped kitchen. *HIGH SPEED WIFI 6 MESH SYSSTEM, WFH friendly. *New & comfortable 2 queen beds which can sleep up to 4people. *65" smart TV. *Safe and friendly neighborhood. *Easy access to expressways, 680,880, 280 & 101. *Many shops and excellent restaurants are within minutes. *Lots of parking spot.

Value · Family · Comfort

Mid Century Modern Living w/Pool

Ever dreamed of living in an Eichler? Now's your chance to experience indoor/outdoor living. Cook a beautiful meal, go for a swim or enjoy a martini on the back patio at this gorgeous mid century property. This is our primary residence which means we are opening up our private space and making room for guests to enjoy our home while we are away. Please inquire if you're a responsible guest who will treat it like your own.

Family · Location · Hospitality

Family sized 4BR, 3 Bath.

4 bedrooms, 3 bathrooms, cozy living room area with gas fireplace, cozy living room, a backyard that feels like a haven. Great for families looking to connect with each other. 2 bedrooms upstairs & 2 bedrooms downstairs. Our home is situated in a quiet residential neighborhood with many walkable restaurants on Lakeshore and Grand Ave. Saturday Farmers market and walkable coffee options are a bonus.

Family · Location · Nearby