Villa holiday rentals in San Francisco Peninsula

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.

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.

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.

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

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*

Incredible Ocean Views from Tuscan Villa Suite

Enjoy this clean, quiet, & comfortable suite in a Tuscan Villa with incredible Pacific Ocean views. Surrounded by nature, you'll wake up to birds singing and watch the sunset in the company of bunnies, red tail hawks, and the occasional deer. Beautiful hikes are right outside the door here in the Golden Gate National Recreation Area. Just 15 minutes from SFO or downtown San Francisco, you are close to everything, but far from the hustle and bustle. You can even walk to the beach if you like!

Camellia Cottage with Pool View (Long Term+)

Reminiscent of a 1920's Hollywood villa, enjoy the aesthetics of that romantic age, yet experience 5 star luxury & the most modern of comforts. Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer, a tropical conservatory, perfect pool and infinity edge spa. Short walk to Woodside downtown and short drive to Highway 280, Silicon Valley, Sand Hill VC firms, Stanford University and Hospital. SFO and SJC are only 25 minutes away. 31+ days discount!

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

Los Gatos Villa: hot tub, sauna, pool, huge yard

Why stay in a hotel when you can stay in this spacious, newly renovated Losgatosvillas executive home within walking distance of downtown Los Gatos? Enjoy your own private 1/2 acre of green lawns, patios, gardens, pool, outdoor dining, firepits, outdoor shower, hot tub, cold plunge, and sauna! This listing includes the master bedroom, 2nd bedroom, office w/futon, 2 bathrooms, chef's kitchen, living room, and outdoor spaces (1 other bedroom is unoccupied and locked during your stay).

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.

Luxury Tranquil Waterfront Haven w/Pool & Spa

Designed for connection, restoration, and quiet indulgence Wake up directly on the water, where mornings begin with glassy canal reflections and evenings melt into golden light drifting in from the bay—just a few peaceful paddle strokes away. Perfect for family gatherings, executive retreats, creative residencies, or refined group escapes, this four-bedroom villa delivers resort-level amenities in a setting that feels effortlessly elegant and deeply restorative.

Villa Waterfront Sunset 4bd 4bth 2Livinrm sleep 16

Our experienced super-host is committed to providing you with a stress-free stay in a spacious, tranquil setting. Experience peace and relaxation at our waterfront property in Discovery Bay, a hidden gem of the California Delta River system—perfect for water lovers. Enjoy breathtaking views of the Delta and easy access to its fast-moving waters. Bring your boat and dock it at our private dock for seamless access to the waterways. Discounts are available.