Holiday rentals with a pool in Wailea-Makena

Excellent location, beautiful view, house was well stocked and the communication was terrific from both homeowner Steve alongside the property manager Walker. Speedy responses to any questions we had. Our family had a blast in Maui and would rent from Steve again. Steve also had great recommendations for local eating alongside a picturesque sunset spot. For our family of five, Steve's home was a winner.

We had the best time at this condo! It was quiet and clean and was exactly what we were hoping for! Don was incredibly responsive when I had questions or needed recommendations to rent baby gear! We had a great time and hope to Come back again

Mike and Ashley were incredibly amazing and helpful. They really went above and beyond for us. Really appreciated the special touch they left us for our anniversary and will recommend them to and friends and family that visit Maui. Their place is beautiful and it looks even better in pictures. It is perfectly homey, private, and quiet, which was very nice but also close to the beach with a three minute walk couldn’t recommend staying with Mike and Ashley more. Thanks for helping make our anniversary trip special!

We, a small family, recently stayed in Kaanapali Maui and couldn’t have been happier with the experience. From the moment we arrived, everything exceeded our expectations. The unit was spotless, beautifully decorated, and fully stocked with all the essentials — from kitchenware including a blender and all of the beach necessities. After going around the island and picking up some fresh fruit, it was a nice afternoon treat to be able to make our own smoothies! Highly recommend it. The view from the lanai (balcony) was absolutely stunning. Every morning we enjoyed our coffee while watching the sunrise over the ocean, and in the evenings we were treated to the most spectacular sunsets. The sound of the waves crashing was the perfect background to a truly relaxing vacation. The location was ideal just a short walk to the beach, shops, and great local restaurants. We loved being close to snorkeling spots and whale watching opportunities. The complex also had a pool, hot tub, and BBQ grill

Pamela was a fantastic host. She was responsive and so friendly. She truly loved the area and making guests feel at home. The space itself was such a dream. It had everything we needed and then some. The location and views were stunning. we sat on the porch almost every night just to take it all in. We loved staying at the Kula Jewel and would stay here again!

Very beautiful location to stay at in Kaanapali! Has a gym with just enough equipment, grills and pools, and an included private golf cart upon request to the beautiful Kaanapali beaches. Also towel service available until 5:30pm! So wonderful! AC and other amenities were great, did not have a single issue or complaint my entire stay here. Had a great time here, will hopefully be back!!!

We absolutely LOVED our stay here. Originally, we were only supposed to stay 4 nights, but we loved it so much that we extended our stay 2 more nights! Jay made it so easy to extend our stay and make us feel welcomed. The location was close to various beaches and restaurants, yet it still felt private. It was calm, peaceful, and exactly what we wanted. The view was absolutely breathtaking and every night we slept with the slider open to hear the waves. We even saw turtles from the balcony!

Luan was a wonderful host, was available with any questions I had. The home was clean and felt cozy. A home away from home. The location was great and was walking distance from the gorgeous beach, shopping, and restaurants. I would definitely stay again and highly recommend.

Amazing spot and stay

The pictures and description don’t do justice to this amazing place! We had the most wonderful time and our expectations were surpassed! The ocean view is much better in person, the lanai was perfect because our toddler could play outside while we enjoyed relaxing in the lanai! Perfect place and really kid friendly! :)

Great service, great stay, would use again.

The place was exactly as described; comfortable and well-equipped. The kitchen had everything we needed, which made cooking easy and enjoyable. The beach is within walking distance, and the walk itself is very pleasant. The home was spotless, cleaning was truly top-notch. The host was very responsive and helpful throughout our stay. While the property is near a street, it’s not an overly busy one, so noise was never an issue. Overall, a great stay that we would gladly recommend.

Dianne’s oceanfront condo in Kaanapali is an absolute gem—hands down one of the most stunning vacation rentals we've experienced. The panoramic ocean views from both the living room and bedroom are nothing short of breathtaking, offering an immersive front-row seat to the Pacific. The space itself is immaculate and thoughtfully designed, blending elegant décor with ultimate comfort. It’s fully stocked with everything you could possibly need, and the bed was exceptionally comfortable. Falling asleep each night to the soothing sound of waves crashing just outside was pure serenity. The location is unbeatable—just a short walk to the local food truck yard, grocery store, and an array of fantastic restaurants. On top of all that, Dianne is a phenomenal host: responsive, accommodating, and truly committed to making your stay perfect. If you’re looking for the ultimate Kaanapali escape, this is it!!

Kalea’s was alway available to answer questions very quickly. The condo was very well taken care of and had everything we needed. Loved the location and area much different than Kanapali as it’s much closer to other areas of the Island to explore. The lights and fan can be tricky at times but remember your own Hawaiian time. Mahalo

My husband, toddler, and I stayed at Kate’s place in Wailea for a week in May. It was fantastic! The location was perfect with easy access to the beach walking paths in Wailea, the shopping center a few minutes walk away, and you have pool and beach access. The grounds are beautiful, including the outdoor patio at the condo. We spent every morning and evening out there! The condo itself was very modern and clean and we appreciated how stocked it was. Kate even had a high chair, pack n’ play, and beach toys for our son. We loved staying here! Highly recommend it to anyone and we likely will be back. The only thing to keep in mind is the unit is close to the main road, so when you are outside there is some road noise.

A gem! Private, quiet retreat in a super convenient location near great restaurants and shops in walking distance, and countless incredible beaches within a very short drive. We loved sitting on the lanai in the morning listening to the birds sing. The condo has everything you need, including beach chairs and umbrellas. Fiona was super responsive when we needed another towel and tissues, sending someone over right away to help us. We loved staying here and wished we could stay longer! thank you, Fiona, for allowing us to experience the beauty of Wailea!