Villa holiday rentals in San Jose

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.

Value · Location · Condition

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.

Family · Value · Indoor spaces

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.

Family · Location · Decor

elegant two-story home in a resort-style community

Surrounded by the serene waters of Foster City's sought-after, the coveted Plum Island community boasts expansive outdoor grounds to create an oasis of peaceful serenity. This furnished elegant two-story home opens to a beautiful yard with picturesque views and is only a few steps to the clubhouse, gated pool, tennis courts, and waterfront that affords the lifestyle you always have dreamed of. There are many good restaurants, supermarkets, and parks within walking or short driving distance.

Value · Location · Walkability

4BD-3BA w/ AC, Parking, BBQ/Firepit Patio near Cal

Experience a modern, freshly remodeled 4BR home with epic outdoor patio/dining spaces, perfectly designed for large groups & families. Centrally located in a safe, peaceful, tree-lined North Oakland neighborhood with a 93 Walk Score - you are steps from the East Bay’s best dining, 10 minutes from UC Berkeley, & a quick BART or Ferry ride to San Francisco. Enjoy a spacious, sun-filled retreat with AC, free parking, Laundry & dual living spaces—ideal for reunions, getaways or corporate stays.

Location · Family · Decor

Luxury Rockridge Retreat-Walkable. Ask to add apt!

Live in luxury in this gorgeously remodeled Rockridge oasis, steps from the center of everything! A sense of relaxation fills the space, whether you are lounging on the front porch or enjoying Al fresco dining on the heated redwood deck! This 3BR, 2 full bath home is perfect for working professionals, couples or families with grown children looking to get away from it all. Larger parties can book the downstairs apartment which sleeps an additional 2- https://airbnb.com/h/rockridge-getaway

Value · Location · Indoor spaces

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 · Family · Nearby

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 · Hospitality

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 · Value · Check-in

Serene Hacienda w/ Stunning Panoramic Ocean View

This light-filled oasis features breathtaking views, major privacy, and wonderful outdoor spaces. A stunning terrace with a round sun bed and dining table for six under the stars! A beautiful deck under the redwoods with a hammock. Open floor-plan, 2,300 sq. ft. Spanish hacienda-style décor, saltillo tile floors, and gorgeous indoor and outdoor plants create an enchanting and secluded space to relax. Feel your cares melt away as you relax in this serene, magical 3.5 acre retreat.

Family · Value · Indoor spaces

Luxury garden villa w/ hot tub and game room

Welcome to our Luxury Villa in the Santa Cruz mountains, a paradise where you can relax and make unforgettable memories. Our villa boasts a spacious patio where you can enjoy your meals surrounded by enchanting gardens. Unwind in our pool, relax in the hot tub, or challenge your friends to a game of pool on professional sized pool table, in our brand-new recreation room. The room features a beautiful handmade walnut bar, complete with a commercial ice maker, sink, and fridge.

Value · Location · Hiking

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

Family · Location · Bathroom