Villa vacation rentals in San Francisco Peninsula

5 out of 5 average rating, 55 reviews

A spacious living area features modern furnishings, with large windows offering natural light. A full-size pool table and foosball table are visible in separate areas. An outdoor basketball hoop and Tesla charging station are also present, enhancing the recreational offerings of the home.

Villa in San Mateo

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.

A bright living area is filled with natural light from an arched window. It features a plush green sofa, a stylish armchair, and a round coffee table atop a patterned area rug. Potted plants add a touch of greenery, and light curtains frame the window.

4.97 out of 5 average rating, 99 reviews

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*

Top guest favorite

An expansive patio features comfortable seating, overlooking lush greenery and the scenic Pacific Ocean in the distance. Soft lighting from hanging bulbs creates a welcoming environment for relaxation. Potted plants add a touch of nature, enhancing the tranquil outdoor space.

Villa in Pacifica

4.97 out of 5 average rating, 197 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!

Top guest favorite

An illuminated home is showcased at night, with warm lights highlighting its architectural features and surrounding landscape. Lush greenery and colorful plants create a tranquil environment, while a spacious driveway leads to the inviting entrance, enhancing the overall welcoming appearance of the property.

5 out of 5 average rating, 29 reviews

Luxury 3BR 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 looking to get away from it all. The fully enclosed Japanese style back garden is great for kids to run around freely, or for adults to unwind after a day of sightseeing.

4.9 out of 5 average rating, 212 reviews

A serene hot tub is surrounded by lush greenery, offering a private retreat. The hot tub is covered, with gentle wind chimes hanging above. Potted plants add a natural touch, enhancing the tranquil outdoor setting, while views of the waterfront are visible beyond.

Villa in San Rafael

Waterfront Marin Retreat with Pool & Hot Tub

5,000 sq ft waterfront luxury villa right at the edge of the canal with private access to the water. Enjoy the heated pool and hot tub, or grab the kayak or paddle board and get on the water from your own dock. The home is 20 mins from San Francisco and Sonoma, has easy access to the 101 freeway, and close to China Camp State Park for hiking or downtown San Rafael. The five bedrooms are perfect for retreats, family vacations, or company off-sites. The spa-like environment is a true getaway.

5 out of 5 average rating, 3 reviews

A sunlit villa displays a charming white exterior with terracotta roof tiles. Two distinct chimneys rise above, while a balcony adds character. Surrounding oak trees provide a natural backdrop, contributing to a serene atmosphere, with gentle hills visible in the distance.

Villa in Woodside

Camellia Cottage with Pool View

Reminiscent of a 1920's Hollywood villa, enjoy the aesthetics of that romantic age, yet experience 5 star luxury pampering & 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. Close to Woodside downtown, Highway 280, Silicon Valley, Sand Hill VC firms, Stanford University and Hospital. A short drive to San Francisco. SFO and SJC are only 25 minutes away.

4.69 out of 5 average rating, 206 reviews

A well-lit bedroom is presented with a spacious bed adorned with layered bedding. A decorative area rug complements the wooden floor. Large windows with soft curtains allow natural light to fill the room. Framed artwork hangs above the bed, adding a touch of charm.

Villa in San Jose

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.

The open living space features a bright, inviting atmosphere with a blue couch, a wooden coffee table, and a plush area rug. Natural light floods in through large doors leading to an outdoor area, while a modern kitchen with stylish finishes is visible in the background.

5 out of 5 average rating, 5 reviews

4 BR Designer Home w/ 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

Top guest favorite

A spacious lawn area is bordered by natural stone features and shaded by trees. Sunlight casts long shadows across the grass, creating a calming ambiance. A wooden chair is positioned on gravel nearby, providing a relaxing spot for guests to enjoy the outdoor space.

Villa in Monte Sereno

5 out of 5 average rating, 39 reviews

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).

4.92 out of 5 average rating, 259 reviews

Villa in San Rafael

Tranquil Waterfront Haven

Explore profound relaxation or supercharged team building relaxation at this 4 bedroom haven with an authentic Finnish sauna with canal views, jacuzzi consciousness, paddle board, a kayak, and replete comfy zones to lazily exchange conversation. The tranquility of the canal will replace all Debbie downer thoughts with a symphony of luminous relaxation, bound to bedazzle wary minds and hearts. Guests will have the full first floor of the house.

5 out of 5 average rating, 18 reviews

A serene outdoor area presents a pool surrounded by lush greenery and blooming flowers. Comfortable seating is arranged on a wooden deck, with a view of the shimmering water and residential spaces in the background. Soft sunlight enhances the inviting setting.

Villa in San Rafael

Marin Poolside Villa

Relax in a private, resort-like setting that includes a pool, hot tub, beautiful gardens and a majestic redwood tree. Located in the Dominican neighborhood of San Rafael, with some of Marin County’s finest weather. Twenty minutes to San Francisco and an easy drive to the Napa/Sonoma wine country. Walk or bike to China Camp State Park and downtown San Rafael.

A modern home is presented with a welcoming facade, highlighted by expansive windows and a multi-level entrance. Lush landscaping with neat plant beds enhances the property, while outdoor seating areas provide spaces for relaxation. The structure is set against a twilight sky, creating a serene atmosphere.