Family-friendly vacation rentals in Pleasure Point

I had a great stay here with my daighter and german shepherd. It was great to have the beach all to ourselves every morning by walking just a block over. The house was beautiful, comfortable, and the greenery outside was wonderful. Would definitely stay again!

The home met out needs perfectly and Sun is a very welcoming host. Our family was very comfortable and we enjoyed the home as a great place to gather and have family time. The home is beautiful and we took great family pictures is the backyard. The location is quiet and felt private.

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

Annie was a great host and the place was exactly as described and just what we needed for a relaxing beach getaway. We loved the hot tub in the backyard and the beach cottage feel of the place. Thank you for hosting us!

We loved our stay ! The house was nice and relaxing and airy , the neighborhood was quiet and easily located near the downtown .

This is a great place for groups and families and young children. It is very clean and well equipped. We came with our children and grandchildren. There is a tree house and a swing in the backyard and a gate for the stairs and bikes and a stroller. The kitchen is great. The location is right near Natural Bridges and West Shore drive. There are lounges in the backyard and a hot tub. We were very happy there. The house has lots of light and comfortable furniture. The master bedroom is amazing and there is a downstairs bedroom.

Julia’s house was perfect. Very clean, well decorated, but not cluttered. It has everything you could need for cooking. It is a very comfortable place to stay.

Loved our tranquil stay here!! The space was super close to downtown Aptos and many hiking spots which made it easy to go in and out. The scenery is absolutely breathtaking and everything we hoped for on our quick getaway. Would stay again!

The cottage was exactly as described. It was very clean, tastefully decorated, and functional. The beach is within walking distance, and there is an ocean view when you stand on the street. The location is superb, situated conveniently between the Monterey Peninsula and Santa Cruz. There are many excellent restaurants within a 15-minute drive. Despite its proximity to these attractions, the area remains peaceful and relaxing.

We had the most amazing stay with our newborn & dog. Walkable to a number of restaurants, coffee shops, and the beach, and a short drive to the cliff walks. We loved being able to put the baby down to sleep in the dark bedroom & eat dinner in the peaceful backyard. Plus, the fenced yard made it easy to let our dog out to go potty (it’s the little things!). We are eager to stay here again!

⸻ 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.

Fantastic stay doesn't cover it! Kim and Pam's bungalow instantly felt like home. This is a fully stocked house with anything you could possibly need - kitchen wares, beach accessories, extra linens, grilling tools! The warm days and cool nights made for comfortable sleeping. We loved using the outdoor shower, relaxing in the hammock and cooking out in the yard. The location, both in proximity to the beach/marina + being in between SFO and Monterey allowed for fun day excursions. Kim's communication regarding all details was exceptional.

Sarah's place was perfect for our family gathering! It was comfortable for 7 and the location was awesome. Only a couple blocks from the beach! The view was nice and we enjoyed eating outside on the pation. Great stay.

Jane’s place was a peaceful quaint spot for our weekend getaway. There’s a beautiful sunroof above the bed which gave great natural light, and the whole place had everything we needed and more, especially the kitchen, despite it size – even though we didn’t cook, in the case of a stay in night, we knew Jane’s kitchen was well equipped, same with the bathroom. Jane was very communicative throughout the whole weekend, with clear instructions on checking in and checking out. She was also very flexible with the check-in time, which we really appreciated. Overall, Jane’s space was a great spot to get away for the weekend and get out of town. Thanks again, Jane!

I had a most wonderful stay at this peaceful and lovely hideaway. The place was ideal and so convenient—to the beach, to Santa Cruz's sights, and walkable spaces—but as perfect as it was, Ron and Nikki were the perfect hosts. Helpful ahead of check-in, responsive and full of great suggestions once I was in, and when I needed to help out a relative, extremely understanding and accommodating. Can't wait to come back!

Had a beautiful stay here. Home is beautiful looks just like pictures . Has everything you need !! Great kitchen beds are comfortable. Linens are great.!! I would just say the driveway is very steep if you drive a low profile car like I do I couldn’t go up the driveway but there’s plenty of parking down below. My son does have mobility issues, but he was able to manage. Thank you again for everything. 😊😊

This neighborhood is safe and peaceful. We have stayed at The Dunes numerous times over the last 4 years. Lisa’s home is beautiful and inviting. We all felt very comfortable and relaxed. It is such a gorgeous area and the staff at the front gate is always so helpful too. I had to reach out to Lisa multiple times throughout our stay and each time her responses were quick and respectful. It was a delight to chat with her and we are definitely planning to come back and would rent this home again.

A recent stay at Robert’s home in Ben Lomond was exceptional. The property felt like home from the pictures on the wall to the books in the bookcase. The fully equipped kitchen, comfortable beds and toiletries was like walking into our personal family vacation home with everything clean and organized. Upon our arrival, we contacted the owner to let them know we arrived. We enjoyed a welcoming orientation of the property. The location was ideal with convenient access to stores and restaurants. We could not have selected a better place to enjoy quality family time and celebrate a graduation from UC Santa Cruz. This was a super stay and gets our highest recommendation.

We had a wonderful short getaway at Sue’s place! The condo is just steps from the beach, pool, and jacuzzi. Falling asleep to the sound of the waves was relaxing, and the ocean breeze was very refreshing. It was exactly what we needed to reset and recharge. Everything was just as described, and we would stay here again! Thank you, Sue!

I half expected to see Jay Gatsby on the balcony when I pulled in. Instead I found Lou very welcoming. The location is convenient to Santa Cruz and Los Gatos. Very peaceful.

Love this place! Will definitely come back!

We had a lovely stay here! The home is well located- easy to visit Santa Cruz and not far to Monterey- there’s also a beach accessible via a short trail next to the house. We enjoyed the view from the roof and the quiet, beautiful garden. Himani was incredibly responsive and quick to help with anything we needed (ie turning on the hot tub and checking in to see if we needed any support throughout our stay). Our little family had a great time enjoying the home and surrounding area and would definitely recommend!

It was a great stay. We loved our time there and would definitely visit again.

Thank you so much Rhea for allowing my family to enjoy this gem! The reviews spoke about the views but wow, incredible! You can literally see up the coast line on both sides. The condo was clean, had enough to accommodate a family of five! We were able to cook our meals every night without a problem. The pool is just a few steps up which my youngest definitely appreciated. We are already missing waking up to the sounds of the ocean! If we’re ever in the area we would be so lucky to book this place again.