Family-friendly vacation rentals in Kaanapali

Tight for a family of six. But loved the location. Can't beat the quick walk to the beach. Very responsive host.

Gal’s place was wonderful. We enjoyed staying there taking Maui’s beauty and especially kihei’s in and then even extending our stay. We’d always come back and will definitely recommend his place. The place is just as pictured. We were grateful for the beach equipment and also that there was a washing machine and dryer that we could use. He and the staff of the place took really good care of us. Don’t hestitate - it’s really the place to be.

We had a great stay at Kihei Bay Surf. We were right across the street from the beach, but when it got too windy, we also had pool access which was very nice. The road was a bit busy, but ultimately not too bad. For those guests that like to cook from their stays (like we do) we found the kitchen well equipped, though you may want to plan ahead regarding seasonings and condiments, etc. There are also a lot of great restaurants nearby (Karen's recommendations were all excellent!) Thanks!

Great location and beautiful view. Perfect size for family of 6. Would recommend!

We loved staying at this condo. It is right across the street from Charley Young beach. That beach is a nice family beach with fun little waves to swim in. We used the umbrella and beach chairs that were in the condo. The condo was very clean and the kitchen was well equipped with everything we needed. We love the location and we had a great vacation at this condo. We would love to come and stay here again!

Exactly as pictured and described. Perfect location, with short walk to the beach, walking distance from shops and restaurants, and fully stocked. Beach closet had everything we needed and more: beach chairs, umbrella, coolers, pails and shovels for sand castles and even water shoes. Kitchen was nicely stocked with pots, dishes, cups, and lots of plastic containers for food storage. We had a great visit!

My husband and I had a positive experience staying at this condo. Communication with the hosts was excellent—they were attentive, helpful, and genuinely caring throughout our stay. While we did encounter a mix-up at check-in, as the condo was still being cleaned when we arrived, the hosts handled the situation with professionalism and kindness. Once the condo was ready, it was spotless, cozy, and perfect for our needs. Our baby, who had been cranky after the flight, settled down and slept all night, and we all enjoyed a very comfortable stay. Despite the initial hiccup, the experience was great, thanks to the hosts’ dedication to ensuring we had a pleasant visit. We would happily recommend this Airbnb and would stay here again!

Kula Jewel is the best Upcountry Maui getaway! The property is far from your every day todo on the island but we like it that way and that’s part of the reason we chose this place. QUIET nights, peaceful surroundings, extremely clean house, and the most wonderful host. Pamela is the most accommodating host I have ever experienced between working with us on check in time, working with us when we needed to leave early, and the excellent recommendations for food and activities. Thank you Pamela for being absolutely awesome! We could not have asked for a better experience.

The location was good for us with easy access to the beach and other island sites. House is well stocked with kitchen accessories, beach going toys, towels, chairs, boogie boards, etc. Owners were responsive and communicated well. House was spacious and met our needs.

We had a fabulous time in Maui and coming “home” everyday to Joe & De’s was just like coming home. Grateful for them sharing their little slice of paradise. It was welcoming and comfortable and we will stay again next time we visit the islands. Mahalo!

This was my second stay at Peter’s cottage and it was amazing yet again. He is constantly upgrading and this time has a new kitchen sink and bathroom sink. The place was private and quiet and spacious for me, my sister and our kids. Peter is communicative while also giving us space, and is a total lifesaver. I will be coming back every time I visit Maui. He embodies the spirit of aloha.

We had an amazing trip and coming back everyday to this condo was so relaxing and felt like home. The condo was in an excellent area with everything you need just a short drive away. I would definitely book again!

The location is great. It was very peaceful.

We've stayed at several different units at this complex. This was the best. Very clean and well furnished. Great location with very attentive host. Several special touches with everything you need ( even had a well stocked mini fridge)! This unit will be our first choice on future trips

Love Sugar Beach and the condo is a bonus with it’s great view. It’s well-equipped with all the necessary incidentals, making our stay comfortable and convenient. Highly recommend! Thank you Mary Anne and Ames!

The apartment was clean and cozy, we had a nice stay, very good and easy communication with Victoria and the location was great. The beach gear available was a plus. Thanks!

Mrs. Barbara was very good at giving us her time every time we had a question about something regarding the condominium. The truth is that my family's stay there was very pleasant. Thanks to her being very kind the whole time. This is something very important that I want to mention. I had to return the unit at 11am, but our flight was not until 4:30 and she allowed us to leave our luggage there for a few more hours. I really appreciate this because our luggage was safe the whole time we were gone.

Great place - will stay again. Complex is nice, quiet and very cleaen. BBQs, small pool. Parking is easy. Walk across to beach and sunset :)

Thank you, Matt! For helping us Celebrate our 25th Wedding Anniversary! It was most definitely an EPIC week.

Manolo is a very helpful and proactive host. He made sure that we were okay and had everything we needed. House is pretty, with a beautiful yard. Manolo has snorkeling equipment, flippers, boogie boards, etc. House is close to the restaurants of Paia Bay (10 min walking), which is great because parking is always a problem in Maui.

I really enjoyed my time here. The view is awesome, and the staff are super helpful. The location is perfect, and everything was really, really clean.

We loved the cottage. It was the perfect for our family. It is towards the back of the whole property and right up against the golf course, so it was very private with PHENOMENAL views. My daughter enjoyed walking the property and picking up rogue golf balls. The layout of the bedrooms is a little strange with two stacked right next to each other and one only having shutters to the rest of the space, but it still served us well. We loved that there was a living room that opened into the kitchen and dining room. My in laws loved having their morning coffee on the lanai. The AC worked great, the only downside is that the AC is not vented into the dining area, but not a deal breaker. When we first arrived (earlier than expected), the AC unit display was not working, but the on island property manager was quick to respond and had someone out to fix asap was just a dead battery. Would HIGHLY recommend, and will stay again if we are on the West Coast. Pools were EMACULATE and great to use!

We had a great time, wonderful location, easy check in, clean and view was fantastic.

Stayed with my wife and 2 daughters. We loved the place! Beautiful view of the ocean, and very well kept. There were beach chairs and a pull cart that made it easy walking to and from the beach (only about a 5 min walk). Would definitely stay again!