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Villa vacation rentals in San Mateo County

Find and book unique villas on Airbnb

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Popular amenities for San Mateo County villa rentals

Private villa rentals

A vibrant, multi-story house is framed by lush trees, showcasing a unique blend of coral and teal accents. The exterior features multiple balconies and an inviting pathway leading to the entrance, emphasizing the property’s scenic hillside setting.
Villa in Pacifica
4.8 out of 5 average rating, 277 reviews

@ Marbella Lane - KnollTop Property | HotTub

LeonRating, 5 stars1 month ago
Just wanted to clarify a comment I saw about being fined or overcharged. From my experience, the host was very clear and fair. We originally booked for 7 people but let her know ahead of time that we’d need space for 10. We paid the extra cost upfront and didn’t get hit with any surprise fees—follow the rules and she’ll be a great host. That said, not all 11 beds are full beds. We used the space for a company retreat where everyone expected their own full bed, so a few folks ended up booking hotels or crashing on sofas. But again, the host communicated all of that clearly in advance.
A calm waterfront scene is displayed, featuring a boat docked next to a gravel shoreline. Reflections of homes and palm trees on the water create a serene environment, while the clear blue sky enhances the tranquil setting.
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.
Superhost
A comfortable bedroom is depicted with a spacious bed adorned with a white comforter and decorative pillows. A round mirror is positioned above a small table, and a bedside lamp provides soft lighting. A floral arrangement adds a touch of color to the room.
Villa in Palo Alto
4.95 out of 5 average rating, 21 reviews

Abby‘s Home|Studio w Kitchen/Bath/AC/private entry

AmberRating, 5 stars1 month ago
I had a nice stay at Abby's place. It had everything I needed while I looked for apartments. Abby was very kind and even gave me lemons and grapefruits from her trees.
Superhost
Villa in Boulder Creek
4.76 out of 5 average rating, 68 reviews

Family Retreat near South Bay and Santa Cruz Beach

AlanaRating, 5 stars2 weeks ago
Lots of space and well stocked. Thanks for a great stay!
Superhost
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
5 out of 5 average rating, 3 reviews

Camellia Cottage with Pool View

BetulRating, 5 stars9 months ago
Definitely five star quality of decor and architecture..Qian was super accommodating, absolutely amazing - so kind, and friendly. And the bed was super comfortable and atmosphere was very tranquil. We felt like we were in Tuscany. I would definitely stay again. Thank you Qian :)
Superhost
An open living area features warm wooden beams and polished flooring. A grand piano sits beside a colorful area rug, while a sofa with cushions adds comfort. Artwork hangs on the wall, and large windows allow natural light to fill the space, enhancing its artistic ambiance.
Villa in Half Moon Bay
4.77 out of 5 average rating, 71 reviews

Seaside Art Gallery Loft Inspire Your Creativity

HarryRating, 5 stars3 weeks ago
Wonderful location right on the beach. Easy access down to the water too. Local restaurant on the street was perfect for laid back dining with good options. Half Moon Bay is a must visit town! Great host and we’ll be staying here anytime we’re in the Bay Area.
Superhost
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
4.91 out of 5 average rating, 182 reviews

❤️ Large Modern Luxurious Villa Near SFO

HussainRating, 5 starstoday
Very friendly and responsive owner .. we had great time there .. thank you
Superhost
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

PaulinaRating, 5 stars1 week ago
Had the best little getaway at Janeen and Rob’s place! It’s at the top of a hill overlooking the water and the town. Super relaxing and quiet place. Lots of good food around and a grocery store just at the bottom of the hill. Super convenient. Thanks again!

Luxury villa rentals

A vibrant, multi-story house is framed by lush trees, showcasing a unique blend of coral and teal accents. The exterior features multiple balconies and an inviting pathway leading to the entrance, emphasizing the property’s scenic hillside setting.
Villa in Pacifica
4.8 out of 5 average rating, 277 reviews

@ Marbella Lane - KnollTop Property | HotTub

LeonRating, 5 stars1 month ago
Just wanted to clarify a comment I saw about being fined or overcharged. From my experience, the host was very clear and fair. We originally booked for 7 people but let her know ahead of time that we’d need space for 10. We paid the extra cost upfront and didn’t get hit with any surprise fees—follow the rules and she’ll be a great host. That said, not all 11 beds are full beds. We used the space for a company retreat where everyone expected their own full bed, so a few folks ended up booking hotels or crashing on sofas. But again, the host communicated all of that clearly in advance.
Guest favorite
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
4.92 out of 5 average rating, 48 reviews

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!
Superhost
Villa in Boulder Creek
4.76 out of 5 average rating, 68 reviews

Family Retreat near South Bay and Santa Cruz Beach

AlanaRating, 5 stars2 weeks ago
Lots of space and well stocked. Thanks for a great stay!
Superhost
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
5 out of 5 average rating, 3 reviews

Camellia Cottage with Pool View

BetulRating, 5 stars9 months ago
Definitely five star quality of decor and architecture..Qian was super accommodating, absolutely amazing - so kind, and friendly. And the bed was super comfortable and atmosphere was very tranquil. We felt like we were in Tuscany. I would definitely stay again. Thank you Qian :)
Guest favorite
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
4.91 out of 5 average rating, 182 reviews

❤️ Large Modern Luxurious Villa Near SFO

HussainRating, 5 starstoday
Very friendly and responsive owner .. we had great time there .. thank you
Guest favorite
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
5 out of 5 average rating, 5 reviews

Exquisite Crescent Suite

KRating, 5 stars5 days 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 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!
Guest favorite
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
4.96 out of 5 average rating, 69 reviews

Ocho Acres~Tuscan style Home with Amazing views

CathyRating, 5 stars1 month ago
Five knitting girlfriends had a perfectly wonderful 2 nights in this Tuscan Villa. It was charming, unique, well stocked and appointed. The surroundings and peace and quiet were so relaxing. The location was a great fit for the concert at Filoli and Half Moon Bay.

Destinations to explore