
Vacation rentals with a pool in San Mateo
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in San Mateo
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for San Mateo rentals with a pool
House rentals with a pool

Oakland Hills home with Pool!
The house for our needs perfectly and Noel was helpful when we let him know of a couple small issues. The kitchen was perfect for our family dinners together so we didn’t have to worry about eating out each meal.

Large Yard w/ Pool. Spacious Single Floor Villa
Host has great communication and understanding. High recommend booking this home!

Silicon Valley Luxury I Sauna, Hot Tub, Pool
The house is beautiful and comfortable and nestled on a hillside with great views of nature and a clear view of the night sky. Enjoyed the fireplace and all the amenities in the home. Would definitely return.

MCM Waterfront Pool/Hot Tub between SF and Napa
Beautiful and peaceful place! Jana & Peter were great hosts.

3 BR Home on Vineyard nr Palo Alto & Stanford
This was an absolutely lovely stay on a beautiful property surrounded by lovely scenery, hikes, and wildlife. Our hosts were extremely warm and welcoming, and very responsive. Very accommodating of some nice amenities for our little toddler, and he appreciated the child friendly environment and the array of games and toys to keep him entertained. Thank you so much for everything!

Bay Area Refuge- Waterfall/Cave Spa, Amazing Views
We stayed at the Treehouse for five nights while we were visiting the Bay Area. We are a family of four (me, my wife, our one-year-old son and my wife’s mom), and all of us love pools/hot tubs and a good sunset. Josie and Russ’s Airbnb delivered on this and more—it was the perfect stay for our family and exceeded our expectations. We felt right at home immediately and always had a response from our hosts within 5 minutes of reaching out. The house is so cool, full of big windows and magical nooks and crannies. The furniture is really nice and the place is stocked with every amenity you could think of, from comfy blankets and towels to sleep masks. The outside is well landscaped, with quality outdoor furniture and trail access to a bucolic hillside where dozens of cows roam all day. The pool and spa is one of the most unique I’ve ever seen, and a truly unforgettable, fun experience. We can’t wait to come back the next time we’re in town!

Beautiful 4 Bedroom Hillside Retreat
A great find, a nice, big house on top of a hill. The converted garage man cave, the swimming pool and a large garden are great additions when it is not winter. The house is also nicely equipped with cooking utensils and amenities. Pinole is also a nice enough little suburb of SF, but traffic might make it a long trip. Next time when our family comes to the East Bay, we will consider this place.

Craftman’s Castle
Great host. Had snacks for free. Filled the propane and bought dishwasher detergent for us. Thank you sir
Condo rentals with a pool

Lakeside Retreat (w/ private parking)
Kirk's apartment was spotless and comfortable. I felt safe being in a gated apartment community (plus, anyone I met in the common spaces was kind). The apartment was only a 5 minute drive to my client's office, there was food close by, and it's super close to the lake. Thank you for having me!

Charming 1 bedroom, 1 bath, 2 Story Condo.
Everything was great! The unit had everything you could possibly need for a trip (stocked bathroom, stocked kitchen, tons of extra towels and blankets). The neighborhood was also very quiet, which was great because we're light sleepers. I would definitely recommend this spot and would stay again.

KING BED | Fully Furnished Luxury Condo Gym & Pool
Great service and communication! We were there for a surgery and he was very attentive and answered all our questions. Close to everything we needed. Very happy with the choice!

Furnished 1 bedroom Apartment, Pool, Gym - Monthly
This is my second time at Henrick’s place and I can’t stress enough how great my experience has been in both times. Not only the apartment itself is great but the peaceful location and the beautiful surrounding adds much more value for anyone who is looking for gate away from the city. It is also very walkable to nearby attractions in Emeryville like the public market and Bay st for great food and shopping spots. And lastly throughout my whole stay Henrick was very communicative and professional making sure my stay was pleasant. I would definitely recommend it and would consider coming back again!!

Stylish Silicon Valley Retreat – Perfectly Located
Great host- from the time we booked the Airbnb until the time we signed out (and after), Kwesi was always available, and genuinely interested in how we were doing G, what else we might need, etc. Great place- clean, quiet, beautiful, nice location.

Downtown Modern Living Condo!
What a gem! Anis's place is spotless, quiet, comfortable, and welcoming, and he was responsive, kind, and helpful throughout our stay. We're looking forward to staying here again the next time we're in town. Thank you so much!

Willow Place
The short version of the review is that, from now on, every time I am back in the Bay Area, I will book this place. It is everything I expect. Now, the long review: The unit is a spacious, quiet and clean unit facing north in a charming building with a very welcoming entrance. The building has the graciousness of 1960s architecture and is well-kept at the corner where two of the most affluent and charming neighborhoods of Silicon Valley meet: close to two Caltrain stations that make your commute to SF and San Jose super convenient. The condo is renovated with great amenities, clean furniture, and a clean bathroom. The bedroom opens to a lovely Magnolia tree that has framed the whole window. Neighbors are quiet and discreet. Parking was indoors with secured gates, another bonus. The location of this property is within walking distance of Stanford Shopping Center, Whole Foods, and Trader’s Joe. Ryan is friendly, very responsive, and communicates well. We will come back again!

Spacious Top Floor Condo Retreat
This place is such a gem that I’m inclined to be selfish and not tell everyone about it! Modern appliances, close to grocery and mass department, clean and recently renovated. Very happy and will book this again!!
Quick stats about vacation rentals with a pool in San Mateo
Total rentals
100 properties
Total number of reviews
860 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
100 properties include access to wifi
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