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Villa holiday rentals in San Jose

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Top-rated villa rentals in San Jose

Guests agree: these villas are highly rated for location, cleanliness and more.

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Villa in Boulder Creek

4.78 out of 5 average rating, 54 reviews

Family Retreat near South Bay and Santa Cruz Beach

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 Boulder Creek. Experience the serene beauty of nature without sacrificing comfort or connectivity. Enjoy a perfect blend of relaxation and modern amenities during your stay!

Villa in Los Altos Hills

4.8 out of 5 average rating, 54 reviews

Exclusive Estate, Paradise in Nature 25567G

Set in the heart of Silicon Valley, this tranquil guest cottage is in an exclusive private estate with an amazing tropical garden view, luxurious gourmet kitchen, and secluded Provence-style living. This cottage has a private entrance with a two-car private parking garage. It also has a pathway leading to a vegetable garden with outside seatings. Bosch EV charger is included. Come to enjoy this one-of-a-kind living experience. The kitchen is equipped with Wolf Stove and a Subzero refrigerator.

Guest favourite

Villa in San Mateo

5 out of 5 average rating, 39 reviews

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.

Guest favourite

Villa in Los Gatos

4.93 out of 5 average rating, 43 reviews

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 3 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!

Guest favourite

Villa in Pacifica

4.97 out of 5 average rating, 179 reviews

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!

Villa in Woodside

4.95 out of 5 average rating, 58 reviews

Ocho Acres~Tuscan style Home with Amazing views

Get away from it all and still be close to everything the area has to offer. Unique Stone Home with sweeping view of Bay Area. Luxurious and well appointed! Close to the ocean and the city, surrounded by nature preserves and numerous hiking trails. 30 miles from San Francisco or Santa Cruz, 16 miles to Half Moon Bay, 30 miles from SFO Airport. Hang out at the pond for a BBQ, visit the local Wineries, hike the many gorgeous trails. Unwind and relax in this magical, unique and stylish retreat.

Villa in Ben Lomond

5 out of 5 average rating, 4 reviews

Santa Cruz Mountains Creek Villa

Embrace the Enchantment: A Fairytale Escape by the Creek. Step into a world of enchantment at our 1923 storybook house nestled beside a babbling creek. Surrounded by redwoods and mountain vistas, our sanctuary invites you to reconnect with nature. Let the soothing sounds of the creek and the tranquil embrace of the forest envelop you as you unwind in this magical setting. Come, experience the serenity and charm of our enchanted retreat, where every moment feels like a page from a storybook.

Guest favourite

Villa in Grand Lake

4.99 out of 5 average rating, 78 reviews

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

Welcome to this spacious and dreamy Victorian villa filled with charming traditional and modern elements. Located around the corner from 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 three floors and has two full kitchens, three living areas, two offices nooks and a tiki barn perfect for entertaining! ✔ Minutes to Attractions ✔ Three Floors ✔ 5BR/4BA ✔ Tiki Barn ✔ Backyard Dining/Patio

Villa in Downtown San Jose

4.66 out of 5 average rating, 187 reviews

SJ Downtown Hensley House Private 3rd Floor

Welcome to the Hensley House of San Jose. It gained historical landmark distinction in 1990. It was the former home of San Jose Mayor Samuel Hensley who was responsible for developing San Jose from a small settlement to a large city in the Mid 1860’s. This house was originally built in 1894 and still retains it’s old world charms, but updated with modern amenities for your comfort. All seven units enjoy their own bathrooms, and large common living area, dinning area, and outdoor garden.

Guest favourite

Villa in Fremont

4.89 out of 5 average rating, 9 reviews

Charming house with lovely garden .

My Mediterranean style home is a very private piece of property located in the heart of Fremont/Silicon valley California Home of Tesla car company and many well know corporations. walking distance from the Wholefoods, Restaurants,Coffee shops , train stations and all kinds of facilities. 2 miles from major freeways of 880 and 680. Most of the top Silicon Valley-companies are located in this town. Bike trails , hiking trails, lakes and Parks only a few miles away from the property .

Guest favourite

Villa in Santa Cruz

4.95 out of 5 average rating, 101 reviews

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.

Guest favourite

Villa in San Mateo

4.9 out of 5 average rating, 173 reviews

❤️ Large Modern Luxurious Villa Near SFO

This newly renovated, modern, relaxing vacation home has an open layout with a large entertainment and family room that can provide a place to stay for a big family or business. Three proper bedrooms and a big walk-in closet that works as a 4th office room. Near the airport, It is perfectly located for your arrival and departure. high-speed internet and Streaming TV. Relax at night in a luxurious hot bathtub with jets. Walk to San Mateo downtown. This is a one-story house.

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Popular amenities for villa rentals in San Jose

Free parking on premises

Air conditioning

Private villa rentals

Villa in Castro Valley

4.93 out of 5 average rating, 90 reviews

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

Guest favourite

Villa in Los Gatos

4.93 out of 5 average rating, 43 reviews

Lovely 4 bedroom gated Villa with free parking

Guest favourite

Villa in Monte Sereno

5 out of 5 average rating, 34 reviews

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

Villa in East San Jose

4.78 out of 5 average rating, 18 reviews

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

Guest favourite

Villa in San Mateo

4.9 out of 5 average rating, 173 reviews

❤️ Large Modern Luxurious Villa Near SFO

Villa in Los Altos Hills

4.8 out of 5 average rating, 54 reviews

Exclusive Estate, Paradise in Nature 25567G

Guest favourite

Villa in Pacifica

4.97 out of 5 average rating, 179 reviews

Incredible Ocean Views from Tuscan Villa Suite

Luxury villa rentals

Villa in East San Jose

4.81 out of 5 average rating, 225 reviews

Entire Villa - Retreat - Refresh - Relax

Villa in Ben Lomond

5 out of 5 average rating, 4 reviews

Santa Cruz Mountains Creek Villa

Guest favourite

Villa in Los Gatos

4.93 out of 5 average rating, 43 reviews

Lovely 4 bedroom gated Villa with free parking

Guest favourite

Villa in Monte Sereno

5 out of 5 average rating, 34 reviews

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

Villa in Boulder Creek

4.78 out of 5 average rating, 54 reviews

Family Retreat near South Bay and Santa Cruz Beach

Guest favourite

Villa in San Mateo

4.9 out of 5 average rating, 173 reviews

❤️ Large Modern Luxurious Villa Near SFO

Villa in Downtown San Jose

5 out of 5 average rating, 7 reviews

100 Executive 4B2.5B 2100 SQFT House J-Town

Guest favourite

Villa in Soquel

5 out of 5 average rating, 9 reviews

Serene Hacienda with Stunning Panoramic Ocean View

Villa rentals with a pool

Villa in Castro Valley

4.79 out of 5 average rating, 24 reviews

By The Bay Retreat

Private room in Palo Alto

4.55 out of 5 average rating, 22 reviews

R4| 4 min to Stanford | Clean & Cozy Private Room

Villa in Hayward

4.95 out of 5 average rating, 40 reviews

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

Private room in Palo Alto

4.67 out of 5 average rating, 18 reviews

R3| 4 min to Stanford | Clean & Cozy Private Room

Guest favourite

Private room in Woodside

4.91 out of 5 average rating, 45 reviews

Estately Plausibility of Simplicity

Private room in Woodside

5 out of 5 average rating, 3 reviews

Exquisite Crescent Suite

Quick stats about villa rentals in San Jose

Total rentals
60 properties
Nightly prices starting at
$13 SGD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi

Destinations to explore