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!

Top guest favorite

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

5 out of 5 average rating, 51 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.

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, 192 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!

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.

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.

4.68 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

4.94 out of 5 average rating, 112 reviews

A spacious outdoor pool lined with a brick border shimmers under the clear sky. Comfortable lounge chairs are positioned beside the pool. Lush green trees and a fenced area provide a serene backdrop to this inviting space.

Villa in Santa Cruz

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.

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

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

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 the motel features a two-story building with a welcoming sign and a red-tiled roof. The entrance is accessible, and a parking area is visible in front, lined with shrubs and trees.

Villa in San Jose

2 Queen Beds|Mini Fridge

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 hotel entrance is framed by tall trees and landscaped bushes, with a covered area providing shelter. A welcoming blue sign is visible above the glass doors, indicating the entry point. Parking spaces can be seen, along with a backdrop of mountains in the distance.

Villa in Gilroy

1 Queen Bed|Ada/Tub

A well-lit room features two full beds with simple bedding, positioned on a wooden floor. An orange accent wall complements the neutral tones. A window with partial curtains showcases an outdoor view. A round table and chairs provide a dining space, enhancing functionality.

Motel 6 Oakland, Ca _2 Full Beds | Nmsk

A comfortable sleeping area is presented with an orange accent wall. A spacious bed is positioned centrally, accompanied by a wooden nightstand with a lamp. A well-lit window offers natural light, while a chair and desk create a functional workspace in the corner.

Motel 6 Oakland, Ca _1 Queen Bed | Ada/T

The welcoming entrance of the Motel 6-Gilroy is framed by lush palm trees and flowering bushes. The spacious driveway leads to large glass doors marked with 'welcome', providing easy access to the lobby area. The surrounding landscape and building are well-maintained.

Villa in Gilroy

MS6 California|2 Full Beds|NS

The exterior of Studio 6 Concord is shown, featuring a three-story building with large windows and a blue awning. Landscaping includes palm trees and flowering plants, while a walkway leads to the entrance, providing a welcoming approach to the property.

Villa in Concord

4.95 out of 5 average rating, 40 reviews

Studio 6 Concord, Ca_1 King Bed | Nmsk

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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!

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!

HeatherRating, 5 stars1 month ago

It was a lovely house for an extended family for a UC Berkeley graduation. The house was spacious - 5 large bedrooms all with king beds! The dining room was lovely for an in home meal. Nice outdoor seating. Spacious living areas. Great off street parking. Friendly service.

Top guest favorite

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

5 out of 5 average rating, 21 reviews

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.

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.

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!

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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.