Family-friendly holiday rentals in Pleasanton

Had a lovely stay at Annette and Fred’s place - the location was great, the house was fully stocked and the hosts were extremely responsive when we had questions. Having a hot tub and gas fireplaces were an added bonus for spending the evenings admiring the views.

We loved this home. The area was great and near everything and the street was nice and quiet for the area. The home was immaculate, the care to maintain this home is obvious! Next time we are in San Francisco, this will be our first choice for lodging.

Tranquility Base…surely lived up to its name. So comfortable, so charming we felt like a part of the forest. The whole place had so much personality we felt right at home Magical and enchanting getaway Highly recommended We’ll be back

Yeshi's home is a museum of colorful artwork from her travels around the world. Wonderful to be lulled to sleep by the ocean waves.

Quiet, peaceful, beautiful garden, responsive host, ample street parking. Definitely worth the price. Plus there's a hot tub you can use after the end of a long day or before the start of one like how we used. MINUTES away from bars, restaurants, and shopping in Oakland. Great location. Thank you so much for the comfortable stay!

Great comfy place. I would recommend bringing your own pillows

Felt like it was just lke my home accept they have a hot tub that I used almost every night during my stay also had a beautiful garden. Is very quiet and relaxing.

Shea’s place was beautiful and spacious for our family of 5. Check in was easy and Shea was very responsive to all my questions about the home and neighborhood. We took full advantage of the backyard with hot tub and ping pong when we needed a break from sightseeing. There was a fair amount of noise from neighbors and the street in the front of the house. All in all we enjoyed our stay.

The place was perfect for our stay. Spacious and has everything we need. Wrich was responsive and helpful.

⸻ I had such a wonderful two-week stay at the farm. From the moment I arrived, everyone was incredibly friendly—especially the sweet little black cat named Teva, who wore a green collar and quickly became a favorite companion. Toni was so kind and responsive, always making sure everything was just right. The farm felt very safe and peaceful throughout my stay. Being in a cabin on a farm, a few bugs are to be expected, but it wasn’t an issue—I came prepared with essential oils, which worked well to keep them at bay. The cabin itself is cozy and compact, but the many windows let in so much natural light that it felt bright and open. The shower was great too—good water pressure and ventilation, though it might be a bit snug for some. Overall, it’s a lovely little escape—close enough to San Jose for convenience, but with a feeling of peaceful seclusion that makes it feel like a true retreat.

The place was very nice. We have kids & grandkids in the Bay Area and like to visit as often as possible. The place was clean and comfortable but most of all very welcoming. And Ramil reached out to make sure our needs were met. If the need arises we would definitely stay there again

Very thankful for this quaint experience! The kids loved the toys and the very kind neighbor helped make sure we had chargers for all the electric toys.

Dennis & Tiiu's place was perfect for our needs. We stayed for a week while in town visiting our son, who lives only a few minutes away, so it was a perfect location for us. The location was peaceful and quite. The house was cozy and suitable for two people. It was a little smaller than it looked in the pictures but again, it worked for the two of us. The amenities were as described. We would definitely stay again.

The place was comfortable and great for an extended stay! Tidy, cozy, and great location! Very clear instructions for the home and check in. Any time i had questions, they were very quick and responsive! I would definitely stay here again!

My wife and I had a wonderful stay at Rick and Heather’s place at woodside. The place is quite spacious and quiet. It is just as described and there were no surprises . If you are looking for a peaceful mountain getaway that is within 30 min ride to Palo Alto, look no further. Things to keep in mind (these are clearly described in listing) are: 1. lack of a true kitchen despite having microwave, toaster oven and a hot plate. I do not recommend any cooking here however since there is no real place to wash dishes or drain etc. 2. The owners live there and although u get plenty of privacy you may run into to them occasionally. If this is not your thing, I recommend you find a different place.

Great place with a beautiful patio! A peaceful stay in the hills with a nice peek a boo view of downtown San Francisco and the bay. Cara is a great host, she is quick to respond and flexible. She is also a good resource for local, fun ideas. She even helped when I left items behind! This is a must stay.

Our stay at Lori and Mike’s place was absolutely fantastic, and Lori truly made it unforgettable. While Mike was away on a trip, Lori went above and beyond to make sure we had everything we needed—and more. From the moment we arrived, she made us feel so welcome. She was warm, thoughtful, and incredibly attentive without ever being overbearing. It’s clear she genuinely cares about her guests and takes pride in creating a comfortable, personalized experience. She checked in with us just enough to make sure we were all set and shared amazing local tips that really made our trip extra special. Her kindness, attention to detail, and friendly energy made all the difference. We couldn’t have asked for a better host. Thank you so much, Lori—you’re truly one of a kind!

Nancy was the nicest and most accommodating host we’ve had at a rental so far. We arrived late one evening when I realized I misplaced the dinner I’d packed to eat when we arrived and when I asked Nancy (who was greeting us when we first arrived) about pizza delivery options, she offered us a nice frozen cornbread pizza to cook in the rental. My hungry young son was so relieved. The backyard overlooks an incredibly green and peaceful hillside and we had such a relaxing time. Also downtown Fairfax is so close by and so adorable. Would love to come back!

The best in San Rafael, plenty of parking and a kayak . Gina is wonderful our guests arrived early so I was asking Gina for early check in Gina response yes right a way Thank you very much. Our guests so happy to stay at your beautiful house. We definitely come back to your beautiful house again! Thanks again Gina

Amy was the perfect host. She was kind and responsive. Great location and beautiful view. We will stay here again!

This place is increíble! Hosts were friendly and proactive. The pool was heated to a perfect temperature and the view is unbeatable. The recommendations for hikes and restaurants were spot on. My husband and I had an amazing little getaway and we’d recommend this place to anyone looking for a peaceful, gorgeous place to stay!

The most incredible home and location!! So far exceeded our expectations!! The setting was gorgeous and serene and perfectly located - short drive to amazing restaurants and vineyards!! We’re already searching for our next opportunity to visit this amazing property!! Couldn’t recommend it more!!!

A lovely property to relax in and enjoy. Just what we needed after doing all the sightseeing in the first part of the holiday

During my stay at Joann’s place, I felt safe and very comfortable. The whole home is bright and spotlessly clean, with greenery visible outside the windows. Parking was very convenient, and communication with her was smooth throughout. The kitchen was fully equipped, allowing me to cook and enjoy a good glass of red wine. The sofa was cozy and the bed was spacious. I was pleasantly surprised to find such a wonderful place—thank you!