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Villa holiday rentals in San Mateo County

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in San Mateo County

Private villa rentals

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.
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
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
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
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
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
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

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 favourite
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
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 favourite
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 favourite
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.
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 favourite
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