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Vacation rentals with a pool in San Mateo

Find and book unique homes with a pool on Airbnb

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Popular amenities for San Mateo rentals with a pool

House rentals with a pool

Superhost
An outdoor space is framed by lush greenery, featuring a stone patio with a garden cottage in the background. A treehouse is visible, along with a covered area and a large blue tarp. Seating is available amidst the natural surroundings.
Home in Oakland
4.8 out of 5 average rating, 101 reviews

Summer-house/OASIS on quiet street in ROCKRIDGE!

JacobRating, 5 stars3 weeks ago
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!
Superhost
A private pool is nestled in a spacious backyard surrounded by lush greenery and trees, offering a view of the hills in the distance. Poolside loungers are positioned on one side, while well-kept gardens and a patio area enhance the inviting outdoor space.
Home in Clayton
4.77 out of 5 average rating, 56 reviews

A Travelers Dream Come Stay with us!

KatieRating, 5 stars1 month ago
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!
Superhost
An overhead view of the living space shows a foosball table beside a light-colored sectional sofa. A chandelier hangs from the ceiling, illuminating the room. An entertainment unit and decorative artwork provide a welcoming touch to the open layout.
Home in Santa Clara
4.8 out of 5 average rating, 5 reviews

Retreat @ Oasis Pool/Hot Tub/Billiards/Game SF Bay

SharynRating, 5 stars1 month ago
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!
Superhost
A serene swimming pool is surrounded by a natural stone border, with a built-in jacuzzi featuring a circular step design. The clear water reflects sunlight, creating a tranquil atmosphere. Poolside lounge chairs and a sheltered seating area are visible in the background.
Home in San Jose
4.84 out of 5 average rating, 44 reviews

Perfect home with pool for family vacations!

DaveRating, 5 stars7 months ago
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.
Superhost
A serene swimming pool is surrounded by a wooden deck, featuring a lounge chair and an umbrella. Sunlight reflects off the water's surface, while lush greenery provides a natural backdrop. A clear blue sky enhances the tranquil outdoor setting.
Home in Oakland
4.89 out of 5 average rating, 27 reviews

Oakland Hills home with Pool!

Maureen NoraRating, 5 stars2 weeks ago
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.
Guest favorite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.94 out of 5 average rating, 358 reviews

Silicon Valley Luxury I Sauna, Hot Tub, Pool

YiRating, 5 stars6 days ago
Very beautiful place, nothing to complain, we enjoy it.
Top guest favorite
The exterior of the home is illuminated under the evening sky, showcasing a spacious deck surrounding the pool. Large glass windows provide a view of the interior, where a dining area and living space can be seen, inviting guests to enjoy the warm ambiance.
Home in San Rafael
4.91 out of 5 average rating, 507 reviews

MCM Waterfront Pool/Hot Tub between SF and Napa

EvaRating, 5 stars6 days ago
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!
Top guest favorite
A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.
Home in Portola Valley
4.93 out of 5 average rating, 149 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

CherylynRating, 5 stars4 days ago
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

Superhost
A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.
Condo in Downtown Oakland
4.92 out of 5 average rating, 287 reviews

Lakeside Retreat (w/ private parking)

KikiRating, 5 stars1 month ago
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!
Superhost
The exterior of the townhouse features a landscaped front yard with low-maintenance greenery, including shrubs and small trees. A concrete pathway leads to the blue front door, framed by an adjacent wooden fence. The two-story structure presents a modern design with a neutral color palette.
Condo in San Jose
4.67 out of 5 average rating, 3 reviews

Charming 1 bedroom, 1 bath, 2 Story Condo.

TomRating, 5 stars10 months ago
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.
Superhost
An outdoor swimming pool surrounded by landscaped grounds is presented, featuring sun loungers and shaded seating areas. The water is clear and inviting under sunlight, and the view of the nearby buildings and trees adds to the serene environment.
Condo in Emeryville
4.87 out of 5 average rating, 30 reviews

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

YasserRating, 5 stars3 months ago
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!!
Superhost
A spacious living room is highlighted by a cozy gray sofa and a circular coffee table placed on a light area rug. A ceiling fan is positioned above, and a decorative piece is displayed on the wall. Natural light filters in from large windows, and a fireplace is present.
Condo in Walnut Creek
4.93 out of 5 average rating, 29 reviews

Downtown Modern Living Condo!

SherryRating, 5 stars2 weeks ago
Anis was an excellent host and the place was as described. Clean and quiet.
Guest favorite
A spacious living area is visible, featuring a large black leather couch and a wooden coffee table. A soft rug lies under the seating area. A dining table can be seen in the adjacent room, complemented by warm wood flooring and ample natural light from nearby windows.
Condo in Menlo Park
4.89 out of 5 average rating, 9 reviews

Willow Place

SiavashRating, 5 stars1 month ago
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.
Superhost
The lake view features multiple sailboats gliding across the water, with a backdrop of tall buildings and a clear sky. Below, a vibrant market scene displays food stalls under palm trees, with a retro sign indicating a nearby venue offering breakfast and lunch.
Condo in Grand Lake
4.6 out of 5 average rating, 10 reviews

Cozy condo by the lake

FareedRating, 5 stars2 months ago
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.
Guest favorite
Condo in Mountain View
4.95 out of 5 average rating, 133 reviews

Spacious Top Floor Condo Retreat

KarrenRating, 5 stars2 weeks ago
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.
Guest favorite
A spacious outdoor pool is featured in front of a modern two-story building, showcasing large windows and a tan stucco exterior. Lounge chairs are arranged around the pool area, with palm trees and vibrant landscaping visible in the background.
Condo in Santa Clara
4.94 out of 5 average rating, 310 reviews

The Alpaca House

RayRating, 5 stars3 weeks ago
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

Destinations to explore