
Vacation rentals with a pool in San Mateo
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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

Summer-house/OASIS on quiet street in ROCKRIDGE!
Great old house, especially for families. It feels lived in by a family (and is decorated as such). That's great esp if you're traveling with your family; there's lots of useful things around the house and entertainments. Neighborhood is great as is the backyard!

A Travelers Dream Come Stay with us!
Beautiful location in the Clayton foothills. Quiet neighborhood with a nearby walking trail that was perfect for our pups. Lots of great space and comfortable beds - exactly what our family needed!

Retreat @ Oasis Pool/Hot Tub/Billiards/Game SF Bay
I booked this home for my colleagues from overseas, and they had a fantastic stay. The host was highly professional and responsive, promptly addressing all requests and ensuring everyone’s comfort throughout their visit. Their attentiveness made the experience seamless and enjoyable. Highly recommended!

Perfect home with pool for family vacations!
Such a nice place to stay in Silicon Valley. Tucked back into the beautiful hills, with a walking loop through the oak trees just down the street. Responsive host. A perfect retreat.

Oakland Hills home with Pool!
This house is incredibly spacious and looks exactly like the photos. All of the linens are well organized and the kitchen had tons of counter space. The fireplace was dreamy in the kitchen and we loved the absolutely enormous television! Very, very soft beds as well.

Silicon Valley Luxury I Sauna, Hot Tub, Pool
Very beautiful place, nothing to complain, we enjoy it.

MCM Waterfront Pool/Hot Tub between SF and Napa
We had a girls trip and found this place to be a perfect Oasis for laughter , connection and many activities in the area . The house had a great feel with many amenities. We really enjoyed the deck with the Hot Tub!

3 BR Home on Vineyard nr Palo Alto & Stanford
We had a wonderful stay at Bill's guest cottage. We found everything as advertised, and the surroundings, especially at sunrise, were serene. The vines were lovely and the morning air fresh and crisp. The beds were very comfortable, and the living space fully accommodated our party of three (two adults, one teenager). We spent most of our daytime out and about with nearby family, so we did not have a chance to try out the kitchen, but it was well-stocked. Bill was highly responsive throughout the booking process and answered our questions. We highly recommend!
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.

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!!

Downtown Modern Living Condo!
Anis was an excellent host and the place was as described. Clean and quiet.

Willow Place
Ryan is a great host answered all of our questions, addressed our requests/needs promptly. A neat safe place near shopping and close to Stanford university met our goal of staying in the area.

Cozy condo by the lake
Selamawit’s places is the perfect spot to stay if you ever have business in Oakland – I was there for a local film festival at the Grand Lake Theater. Matching the tranquil location that was within walking distance to all of the excitement of grand Avenue was the impeccable and spacious home as well as Selamawit’s consummate hosting. She was always available, flexible, and attentive to my needs. It was a pleasure to stay in her space I hope to stay there the next time I find myself in the Bay Area.

Spacious Top Floor Condo Retreat
A very nice location with many super markets (whole food, Walmart etc.) nearby. The place is neat and clean with all the things you need. The host is very kind and responsive.

The Alpaca House
Highly recommend this condo located at Rivermark. Great and safe place for family stay! We enjoy the bed and had sound sleep. The host is so responsive and solved out kettle problem quickly. Definitely the to-go choice for stay in Santa Clara/San Jose.
Quick stats about vacation rentals with a pool in San Mateo
Total rentals
100 properties
Total number of reviews
870 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi
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- Golden Gate Park
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- Muir Woods National Monument
- Mission Dolores Park
- Golden Gate Bridge
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- The Forest of Nisene Marks State Park
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- Glen Canyon Park
- Six Flags Discovery Kingdom
- California’S Great America
- Pasatiempo Golf Club
- SAP Center
- Big Basin Redwoods State Park
- Henry Cowell Redwoods State Park
- Painted Ladies
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