
Vacation rentals with a pool in San Mateo
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Top-rated rentals with a pool in San Mateo
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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!

Fully renovated private cul-de-sac home in Marin
Courtney's house was a beautiful place to stay in San Rafael. It was meticulously designed, and even more tasteful and well-curated than we expected. It was everything we wanted for a tranquil northern California retreat. We've been recommending it to all our friends and relatives who need a place to stay in Marin County.

Luxury 4-Suite Carbon-Neutral Home With Pool
Dan was a great host! He was quick to respond to any questions/concerns during the stay. We actually had a hiccup or two during the stay, and he was prompt to fix the issues by having someone come over to resolve them within 2 hours. The home is beautiful and spacious and has basically all your kitchen needs, so that's always great to have! 10/10 recommend

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.

Silicon Valley Luxury I Sauna, Hot Tub, Pool
Lovely staycation, detox and adult time. The sounds of the frogs permeated the forest as we soaked in the hot tub and the ambiance was impeccable. The sauna was lovely and bed super comfortable. I thought we might play pool but we spent more time in the sauna and hot tub. I would stay again and try to come earlier to enjoy longer.

MCM Waterfront Pool/Hot Tub between SF and Napa
We had an absolutely wonderful time at this incredible home that backed up to the lovely waterfront and had a delightful deck and patio, surrounded by lunch plant life, with pool and hot tub. The house was spacious with streaming light from many large, beautiful windows, fantastic hard floors, and incredible amenities! we can’t wait to revisit this home with such wonderful hosts!

The Happy Hideaway - Pool, enjoyable backyard!
Mei's place was perfect for our visit to Hayward! The neighborhood was quiet, the layout was spacious, and our group of 6 adults and 1 baby had everything we needed. We would definitely stay again - hopefully in the summer when we can really utilize the incredible backyard space!

3 BR Home on Vineyard nr Palo Alto & Stanford
I tell my local partners and friends in SF Bay they should send their visitors to stay. We have stayed multiple times and thankful for the pickleball, country walks on the property, stocked kitchen with utensils and cooking supplies, and clean linens. It was smaller than expected the first time, but we figured it out because the land and entertainment value of the courts and trails more than compensated the need for more bedroom space. We’ll be back again without a doubt.
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.

Fully Furnished Condo near Tech Giants & Stanford
Isaiah was a great host. Very responsive and great communicator. The apartment is very nice. Modern and clean and so is the complex. Highly recommend the place.

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
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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- Golden Gate Park
- Stanford University
- Washington Square
- Capitola State Beach
- Sumner Beach
- Joaquin Miller Park
- Children’S Fairyland
- Corcoran Beach
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
- Surfers Beach
- El Granada Beach
- The Forest of Nisene Marks State Park
- Glen Canyon Park
- Big Basin Redwoods State Park
- Point Reyes National Seashore
- SAP Center
- Mission Dolores Park
- Oakland Zoo
- California’S Great America
- Six Flags Discovery Kingdom
- Henry Cowell Redwoods State Park
- Pacifica State Beach