Family-friendly vacation rentals in Wailea, Wailea-Makena

We had such great time during our short stay. The listing was just as described, with all the beach amenities provided, towels, chairs umbrella, etc. The location was right off the beach, yet very quiet during the night. Highly recommend staying here.

Couldn’t have asked for a better place to stay for our first trip to Maui! The photos don’t do the unit or grounds justice. The sound of the ocean, tropical plants, gorgeous sunsets and whale watching from the condo/beach area… made it SO hard to leave. Would definitely stay here again!

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!

We couldn’t have asked for a more perfect house/location. It had all the space and amenities to make it a comfortable stay for our party of 6. We loved waking up every morning and walking over to Kraken Coffee for a delicious cup of coffee and then later walking over to the food trucks at night for an amazing variety of food for dinner. Probably our absolute favorite thing was how conveniently close Foodland grocery store was. We would love to stay there again in the future! Mahalo!

We enjoyed our stay. It was very close to all the places we went. The place was comfortable, and we had all we needed. Loved the stocked kitchen and amenities.

We enjoyed our stay at Heather’s place. Good location. Walking distance to the shops and oceanfront walk. Appreciated the chairs and umbrellas provided for the beach. Had everything we needed for our stay.

Perfect stay for my family. Every works and having beach gear provided was so nice!

Loved this adorable unit. It was perfect for my holiday. Highly recommend. Maui is beautiful! 💗

Great great great!! Location and communication were as good as it gets. Can’t wait to come back.

Great spot on the coast, one of the few with a beach and easy ocean access if you want to swim in the morning. Beautiful rainbows and whale watching each morning and the hot tub is nice if you have lower back problems. No a/c in the unit is the only curveball but tough to beat the location and natural beauty

We had a fantastic stay at Ken’s condo in Wailea! The location was perfect—just a short walk to great restaurants, coffee, and shopping. The highlight was the stunning ocean view from the lanai, where we enjoyed relaxing every day. The condo was well-equipped for our group of six (three couples), and we especially appreciated the beach gear, including chairs and umbrellas. It made our beach days so much easier! The only minor downside was that the beds weren’t the most comfortable, but overall, we loved our stay and would highly recommend it!

Steve’s place is great and he is an excellent communicator and very invested in ensuring his guests have a great experience. We loved watching the sunset from the deck and the pool and game room were both so fun for our family. Lots of pantry staples on hand as well as some yummy snacks to greet us. The location is private and peaceful and we loved all the beautiful Hawaiian plants and geckos in the yard. Thanks for a great stay!

Such a great house. Stayed at a few rentals in Lanai and by far this is the most homely. We loved it and hope to be back

Fantastic place to stay on Maui. Staying in the Upcountry let's you hit all the major sights easily, while also having peace and quiet (and cooler weather!). The views from the house were sublime. Pamela was a wonderful host. she met us at the house despite getting there late in the dark. we were in frequent contact and she gave us all sorts of insider tips about routes to take and placed to stop. that part of the experience was invaluable! would definitely return!

Emma’s place was perfect. We absolutely loved staying there. It was so easy to get to everything we wanted to see and do, it’s quiet and peaceful at her place and she makes your stay very easy and relaxing. She’s a very responsive host and sent so many great recommendations on local places! I’m so glad we stayed at Emma’s and would again!

We thoroughly enjoyed our visit to the Turtle House. Poni was wonderful, location made us feel like we were locals. Beaches were amazing, so many fun restaurants to choose from. Her guide book was second to none, recommendations were spot on. We will definitely stay here again.

Fabulous accommodations with a beautiful view of the water. Really nice new furniture and well stocked with everything we needed. Easy walk down to the beach for the sunset. We appreciated the high speed WiFi for our zoom meetings without a glitch. The host was great - we would stay again and highly recommend this Kihea condo with a view.

Very spacious apartment on a beautiful and peaceful property with amenities. Walking distance to the beach and short drive to other beaches and surf shops. The unit had everything we needed like a full kitchen and beach towels, as well as the washer and dryer which came in really handy. Yuana was super responsive and accommodated our requests and questions!

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 place and pictures is exactly as described. Such a beautiful place, very well equipped little home and fit our family of 4 perfect. I think one of the best amenities was all the stuff for the kids/adults in the closet for fun beach activities! The pool was a beautiful bonus as well. We love Kīhei and we would definitely stay here again! Wish we could have stayed longer! Mahalo for being great hosts and highly recommend your place to anyone! 🤙🏼🌺🌴

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!

Kanako was amazing and their place was even more amazing. We traveled as a family of five adults and one child and this was the perfect amount of space for all of us. The pools were both great. Walking distance to the shoppes of Wailea, lots of food options, coffee shops and other shops near by. We did have a small issue with the tv that it stopped working completely and kanako resolved the issue almost immediately. It was a fully stocked kitchen that we were able to cook some meals in. It really felt like a home away from home. The place was PERFECT!! We would definitely stay here again and again!!

Very comfortable stay for my family of four (me, husband, kids ages 6 and 9). Lots of beach gear such as umbrellas, chairs, snorkels, sand toys, small cooler, boogie board/body boards, tennis rackets and ball. The patio has so many trees and plants that it feels very secluded and peaceful. The condo was not too far from Safeway for groceries, kitchen was well stocked with pots, pans, utensils, Tupperware. The beach that is within walking distance would probably not be the best one for swimming, but good for a walk. Beaches to swim and play in the water are close driving distance. The condo was clean, spacious, and a good location. I would definitely stay there again.

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!