Villa vacation rentals in San Francisco Peninsula

4.76 out of 5 average rating, 68 reviews

Villa in Boulder Creek

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!

5 out of 5 average rating, 51 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, 94 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*

4.97 out of 5 average rating, 192 reviews

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

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!

The back exterior of the home displays multiple levels with large windows, providing ample natural light. Lush greenery surrounds the property, including a variety of plants and trees. A patio area is visible, featuring a shaded umbrella over a dining table.

5 out of 5 average rating, 23 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.

4.96 out of 5 average rating, 69 reviews

A rustic stone home is surrounded by lush greenery and sunlight filters through the trees. The two-story structure features a red-tiled roof, dark wooden shutters, and a charming balcony. A gravel path leads to the entrance, framed by colorful plants and bushes.

Villa in Woodside

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.

4.89 out of 5 average rating, 208 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.

4.68 out of 5 average rating, 200 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, 3 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

4.92 out of 5 average rating, 255 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.

4.91 out of 5 average rating, 182 reviews

A lush garden pathway is surrounded by vibrant greenery and mature trees. Natural stone stepping stones lead to a seated area with a bench, offering a quiet spot to relax amidst the foliage. Spaces for growth and tranquility are evident throughout the garden.

Villa in San Mateo

❤️ Large Modern Luxurious Villa Near SFO

Modern, newly renovated one-story home with open layout, perfect for families or business trips. Features 3 bedrooms plus a walk-in closet that can serve as a 4th room or office. Enjoy high-speed Wi-Fi, streaming TV, and a jetted hot tub. Step into our lush garden—like a private botanical park—peaceful, fresh, and full of charm. Walk to downtown San Mateo, minutes to the airport.

A serene outdoor space features a wooden dining table surrounded by chairs, set against a backdrop of lush gardens. Mature trees provide shade, and a gentle path of stone steps leads to the seating area, inviting relaxation amidst the natural beauty.

4.79 out of 5 average rating, 14 reviews

Private hilltop 3-4 bd estate in Upper Rockridge

San Francisco from the Heart of the East Bay's Upper Rockridge. With 360-degree views of San Francisco Bay it is like living in a postcard. For you and your guests, a secluded property, indoor/outdoor living, 4 bedrooms, 3 full baths, sleeps 6-8. Perfect for families, Centrally located for exploring the San Francisco Bay Area and Napa Valley.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for San Francisco Peninsula villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

The spacious suite features two queen beds, each adorned with floral patterned bedding. A comfortable couch is positioned nearby, complemented by framed floral art on the walls. Soft lighting enhances the cozy atmosphere, and a warm wood-tone floor adds to the inviting ambiance.

Villa in Castro Valley

4.93 out of 5 average rating, 90 reviews

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

StevenRating, 5 stars33 months ago

Great host, great location. Property is a gem, clean and quiet. We will stay there again.

The exterior of a two-story house is displayed, featuring a light green facade and white trim. A vibrant red bougainvillea blooms in front, complemented by landscaped flower beds and decorative stones. A double garage with white doors is visible, along with a well-maintained pathway.

Villa in South San Francisco

The ideal vacation home in So. San Francisco

AnnieRating, 5 stars14 months ago

Very conveniently located in SSF!

The exterior of a remodeled single-story house is presented, featuring a front yard with various shrubs. A driveway and a gated entrance are visible. Tall trees border the property, with abundant natural light illuminating the front. The overall design portrays a welcoming presence.

Villa in San Jose

4.5 out of 5 average rating, 22 reviews

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

NateRating, 5 stars2 months ago

I stayed for 3 months and couldn’t have been happier with my choice to stay here. Close to downtown, amazing food all around. The gate in front and the fact it was at the very end of a cul de sac made the place feel extra private. Would definitely recommend!!

A single-family house is seen from the front yard, featuring a light-colored exterior and a shingled roof. Landscaped gardens with low maintenance plants and pathways lead to the entrance. The driveway accommodates parking, with trees and additional greenery enhancing the outdoor space.

Villa in San Jose

4.91 out of 5 average rating, 22 reviews

A Gem! Executive 4B2.5B 2019 SQFT House J-Town

NormaRating, 5 stars1 month ago

The best part of this place was the room in the back. It really was like an Executive Director suite. So of course my ED took advantage and took the room for himself. lol. We appreciate the extra blankets and we each had our own room.

The exterior of a two-story motel building is shown, featuring a central courtyard with landscaped greenery and palm trees. The structure is illuminated with outdoor lighting, displaying individual room entrances with blue accents and large windows on both levels.

Villa in Hayward

MS6 California|1 King Bed |

The exterior of a two-story motel building is shown, featuring a combination of light-colored walls and a welcoming entrance. A spacious parking area is visible, accommodating several vehicles. Lush green grass borders the pavement, and a clear blue sky enhances the overall setting.

Villa in Fremont

MS6 California|1 Queen Bed|NS

An exterior view of a two-story motel building is featured, surrounded by a well-maintained parking lot. Multiple vehicles are parked in designated spaces, and landscaped greenery borders the area. Clear blue skies provide a bright backdrop, enhancing the property's welcoming appearance.

Villa in Fremont

MS6 California | 1Q | MobAcc | NS

Villa in Hayward

4.95 out of 5 average rating, 40 reviews

MS6 California|2 Full Beds|NS

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Luxury villa rentals

The indoor pool is enclosed within a dome structure, featuring clear water reflecting soft light. Textured walls and a spacious pool deck provide ample room for movement. A wooden bench is positioned along one side, enhancing the tranquil environment.

Villa in Hayward

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

MichaelRating, 5 stars11 months ago

We had an absolutely fantastic time staying at Lior’s place. From start to finish, everything exceeded our expectations. The communication with Lior’s was smooth and prompt. Upon arrival, we were warmly greeted and given a thorough tour of the property. The pool was amazing it was heated all the days of our stay regardless of the weather it was great going in , space was immaculately clean and beautifully decorated, providing a cozy and welcoming atmosphere. The amenities provided were top-notch, ensuring that we had everything we needed for a comfortable stay. Thank you!

5 out of 5 average rating, 21 reviews

The exterior of a two-story house is shown, featuring stucco walls and a tiled roof. Two palm trees stand in the yard, and a driveway provides access to the attached garage. A clear sky is visible above, adding brightness to the scene.

Villa in Discovery Bay

Villa Waterfront Sunset 4bd 4bth 2Livinrm sleep 16

JudyRating, 5 stars2 weeks ago

Sang’s home was beautiful, clean, and incredibly spacious — perfect for our group getaway. The house was well-stocked, comfortable, and had everything we needed for a relaxing and fun stay. We cooked, enjoyed time out on the boat, and had such a great time as a family. Communication was clear and helpful throughout the process. Highly recommend staying here if you’re looking for a peaceful and enjoyable escape in Discovery Bay!

4.92 out of 5 average rating, 48 reviews

The sunlit pool area features a clear blue water surface, complemented by elegant lounge chairs. Surrounding the pool, well-maintained stone decking is visible, leading to picturesque architectural elements typical of a villa. Lush greenery and mature trees provide a serene backdrop.

Private room in Woodside

Estately Plausibility of Simplicity

AimeeRating, 5 stars2 months ago

I recommend this beautiful home! It’s extremely private and everything you’d need …. and more!! The inside is luxurious and the outside grounds are beautiful and relaxing. It’s truly a gem getaway!

A sunlight-filled living room features a modern sectional sofa with colorful accent pillows. A round coffee table is centered on a vibrant green area rug. The walls are adorned with windows, inviting natural light, and a decorative fireplace adds warmth to the space.

4.95 out of 5 average rating, 19 reviews

FirePit|BBQ|Outdoor Dining|Near UC|Spacious & Lux

SteveRating, 5 stars6 months ago

This was the perfect place for us to visit with our three adult children, since there was plenty of space for everyone. It’s a fairly central location in Oakland with many walkable areas between 15 and 30 minutes away. Not really in any specific neighborhood but close to many. Large attractive, outdoor space and plenty of privacy. Alli was a great host and extremely responsive when an issue came up.

The exterior view features a Spanish Mission-style home with a tiled roof and white stucco finish. Lush greenery and colorful flower planters frame the entrance. A paved driveway leads to a garage door, while a balcony above offers an additional outdoor space.

Villa in Castro Valley

4.97 out of 5 average rating, 33 reviews

Clean And Classy 3 Bed Villa, Great Family Retreat

WilliamRating, 5 stars32 months ago

Beautiful place to stay.

5 out of 5 average rating, 5 reviews

A spacious living area features a large bed with soft linens, complemented by a marble table and stylish chairs. Large arched windows allow natural light to fill the room, showcasing views of the surrounding greenery. Light-colored walls and exposed wooden beams enhance the airy ambiance.

Private room in Woodside

Exquisite Crescent Suite

KRating, 5 stars1 week ago

Qian has such vision. I’m inspired by her. It’s fascinating to stay here & quite difficult to return to my own reality.

A serene backyard is visible, featuring a covered patio with an umbrella, a rectangular pool covered with a blue tarp, and lush greenery surrounding the area. A dining table with chairs is positioned nearby, providing an inviting outdoor space for relaxation.

Villa in Piedmont

5 out of 5 average rating, 18 reviews

Family sized 4BR, 3 Bath.

DaveRating, 5 stars4 weeks ago

Michael’s place was perfect for our family gathering and Michael and Joanie were super hosts—warm, thoughtful, very communicative. The backyard cabana and pool area are wonderful. It felt like we were at a tropical beach and made lots of family memories there. Thanks again for letting us stay in your home!

A modern kitchen is presented with light wood cabinetry and a large central island. Stainless steel appliances, including a refrigerator and stove, are visible. Three pendant lights hang above the island, complementing the open layout that connects to the living area.

Villa in Menlo Park

4.81 out of 5 average rating, 27 reviews

Mid Century Modern Living w/Pool

MicheleRating, 5 stars10 months ago

This was just the respite we needed from San Francisco. Spending almost a week hanging out by the pool, close to restaurants when we didn’t want to cook, and with enough space for my entire family to stretch out was absolutely amazing and super relaxing. We felt right at home. Thank you, Azadeh!

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Villa rentals with a pool

4.89 out of 5 average rating, 18 reviews

A serene outdoor space is showcased, featuring a dark pool reflecting surrounding greenery. A small table with decorative items is positioned next to a single chair. The walls are lined with plants, and sun casts gentle shadows on the concrete patio.

Private room in Novato

Ranch Style Wine Country Escape

JeffRating, 5 stars10 months ago

This place is lovely - a family home - pool - gardens. The on-site host Rue - an aspiring actress - is very sweet - and believable - hope you got the part!

Villa in Foster City

4.75 out of 5 average rating, 4 reviews

elegant two-story home in a resort-style community

MarjorieRating, 5 stars26 months ago

Beautiful neighborhood. Many walkable trails and parks with access to the Bay Trail. House is large and comfortable (great beds) and spotlessly clean. Large private backyard and very close to the tennis/pickle ball courts and pool. Only complaint is that the kitchen was not well stocked for our two week stay. We needed to borrow cooking implements and equipment from our son who lives in the area. But overall, a wonderful property and would not hesitate to return.