Villa holiday rentals in San Francisco Peninsula

Family Retreat near South Bay and Santa Cruz Beach

Permit# 231447 Escape with friends and family to the mountains, the beach, and the bay—all in one place! Enjoy views atop the vast mountains encompassing Boulder Creek, just 30 minutes from the Santa Cruz boardwalk and beach and 40 from South San Jose. Take advantage of nearby state parks and hiking trails, and visit the tranquil town of BC. Experience the serene beauty of nature w/out sacrificing comfort or connectivity. Enjoy a perfect blend of relaxation and modern amenities during your stay!

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. Come and enjoy a relaxing time at Villa Miro!

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.

Luxury 3+BR Rockridge Retreat-Walk to everything!

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

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, and 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).

Spacious & Luxurious Home near UC Berkeley

Perfect for groups & families – 4BR, 2 living rooms, 2 full kitchens, and an epic backyard BBQ setup. Features 2 spa-like bathrooms with serene showers, plus in-unit laundry. Centrally located in the city, walking distance from the East Bay's best bars & restaurants. Enjoy spacious indoor-outdoor living near neighborhood parks. Easy access to highways & public transit gets you to San Francisco in minutes. Close to UC Berkeley and Ideal for reunions, getaways or work stays.

Alamo Estate Living

Alamo is conveniently located between Danville and Walnut Creek in the Rt 680 Corridor. Our home is 10 minutes from BART and 30 minutes from San Francisco. You can drive to wine country in 45 minutes. Our home is good for business travelers, families, and large groups. We are convenient to shopping, great restaurants and entertainment. Our amenities are all self contained and private. A great home to make your visit a memorable one. We welcome hearing from you.

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.

Mid Century Modern Garden Home

Bring the whole family to this beautiful and unique getaway with lots of room for fun. No other space like this just 30 minutes from San Francisco. The main home shares an an enormous backyard with another home on an acre of beautiful gardens with native plants and flowers, kids playground, hot tub, sand pit, huge walnut tree, back patio with an outdoor wood fired pizza oven and fire pit.