
Waterfront holiday rentals in Wailea, Wailea-Makena
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Top-rated waterfront rentals in Wailea, Wailea-Makena
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Waterfront apartment rentals

Kauhale Makai - Oceanfront Property
Very nice property, clean and very well located.

100 steps from the beach! Tranquil Seaside Oasis
Exactly what I hoped it to be! Good price for the area, and the host really put in extra effort to have good local recommendations and to clearly communicate the instructions/expectations, plus she was very friendly and responsive. Overall, the stay was very straightforward, easy, and pleasant!

Maui Calling! Oceanfront Condo with Amazing Views.
My husband and I really enjoyed our brief stay here! The beachfront ocean view from the Lanai was absolutely stunning, definitely our favorite thing about this unit! The place was clean and looks just like the photos. King sized bed is comfortable. Theresa was very responsive. Would highly recommend anyone to stay here if you plan to be on Maui for at least several days or longer!

Amazing Oceanview! Beach, whales! Family Fave!
Great stay for a week of R&R in Kihei in March 2025. Good location in North Kihei with a west view of the water. Good value for the price. Not many walkable restaurants nearby but only a 5-10 minute drive into Kihei for a bigger selection of restaurants. Was a great home-base for our visit. Would recommend to others looking for a non-resort style vacation in Maui! Worked really well.

Sugar Beach Resort #532 - Maui HI
We had a wonderful time at Lucy and Alan’s condo. The location is perfect - right on the beach. It is so peaceful and tranquil. It’s only a short walk down the beach to the bakery, the ABC store, shave ice place and farmer’s market stall for fresh fruit and smoothies. The complex also has a sandwich store on premises and an activity center we used to rent snorkel gear and book a luau. The pool and hot tub area was great to use after a day of exploring the island. The location is perfect - you can go north to Kaanapali, or south to Wailea both are about 20/30 minutes away. The condo had everything we needed and the central air conditioning was perfect when the days were warmer. There was nothing like hearing the waves crash and watching the canoes float by while eating breakfast every morning. I’m going to think about this trip for a long time. Lucy and Alan’s place made the trip perfect for us. Highly recommend this location for your Maui adventure. We will be back!!!

Next to Beach, Foods & Shops - Updated w/ View!
Place was perfect for our family. Literally across the street from an amazing beach. Next door to restaurants, coffee shops and ice cream shop. (Get the fish tacos at Coconuts!) We enjoyed the beach gear that was provided (chairs, umbrella, toys, cooler). Highly recommend!

Charley's Hideaway (Oceanfront)
I've been vacationing in Kihei, Maui, for 30 years, and this place is amazing. Walk out the door onto the Charley Young beach. Sleep hearing the waves crashing and feeling the beautiful ocean breeze. His place was super spacious. I've rented two bedrooms before, which were half the size and cost twice as much. His place is genuinely one of a kind. Fully stocked with sun umbrellas, boogie boards, and beach chairs. You'll immediately be ready to hit the beach. Derrick is a descendant of Charley Young and has an impressive amount of island knowledge, as well as wonderful adventure and food tips. Derrick is incredibly chill, and if I were to move there, I would want to be his friend.

Oceanfront penthouse with amazing views at Kauhale
Gabriel was very friendly and accommodating, following up from time to time to make sure everything was in good order. His home was well furnished and well supplied. He even quenched our morning coffee craving with a well stocked supply of Keurig coffee pods! The ocean view from the condo was incredible, and the complex had nice amenities. Gabriel's home is centrally located and provides a good home base for activities all over the island. We would definitely rent Gabriel's condo again if we make it back to Maui!
Waterfront house rentals

Brand Newly Remodeled Luxury 2 BR - Kapalua Golf
We loved our stay at this place. The location in Kapalua and the beautiful grounds were unbeatable. There were just a few hiccups initially but they were resolved within 24 hours. Firstly the AC was not working which was hard with 2 young kids and the warm climate. The company was going to send a tech but he wouldn't be in until the next day so luckily my husband was able to fix it in the meantime. Secondly, we had ordered and paid for a pack and play which was supposed to be in the unit on arrival but did not arrive until 9 pm (already after my child needed to go to sleep). I was told this would be refunded by the lovely manager Scott who came to deliver the pack and play. He was also kind enough to lend us his binoculars for whale watching :) The unit itself is beautiful. Very new and clean and exactly as the photos. We would 100% rebook if staying back in Kapalua, Maui.

Island-Inspired 2BD Oceanfront ~ Quam Properties
We stayed in two units at Hololani. This one was my fav. More spacious. Wonderful lanai. Unit is comfortable and we felt at home. Made some great dinners and enjoyed the view. This is a neighborhood condo not the high end resort. Pool amazing. 90 degrees! We loved our stay! Note units are Not air conditioned. Fans adequate. A couple of big box fans would have gone a long way to making us more comfortable.

Hale Hookipa Kai House, County Licensed
Had an amazing time. Loved the view of the ocean and the sound of the waves. Made it my morning routine. Definitely want to come back.

Luana Kai C209
Beautiful condo in Kihei with every possible amenity to make you feel right at home. Private and peaceful with a pool, beach access. Perfect for getting around to snorkeling which was nearby. Access to stores too. Great place from which to visit Haleakala as well!

Beautiful Beachfront Townhouse !
We had a fantastic and memorable stay at Doug's place in Kihei. You can't beat the location--right in Kihei yet set back down a private road and right on the beach. The views out of the windows are amazing, and within a short walk your feet are in the sand, at the ocean's edge where turtles are peaking their cute little heads out consistently. We even encountered a turtle lounging on the beach! The house is stocked with the basics: plates, cups, coffee maker, toaster, nice towels, etc. The beds are comfortable and with the windows open and the fans on, the island breeze keeps the house very comfortable. Doug also has beach chairs and an umbrella for easy lounging. Highly recommend Doug's place!

Centrally located and steps to the beach!
Mike and Ashley’s place was perfect for our little getaway. It was one of our birthdays and they had a little balloon and card for us. They were very responsive when we needed a couple of things and I 10/10 recommend to stay here!

Maalaea Kai 307 - Maui Prime Oceanfront
This was a fantastic place to spend our week in Maui. The condo was amazing and spacious with all the amenities you would need to enjoy your time. The location is perfect, relatively close to the airport and well situated next to route 30 so you could go everywhere on the island quite easily. The view from the condo is second to none, from the patio you can easily see the Haleakalā mountain and from the front door is a great sight of the western Maui mountains. And on top of everything this condo was much more peaceful than the huge resort areas. There were not too many people around, and even when we did go to the beach we were able to find a spot easily. I’d recommend this condo for anyone who wants to spend a week or a few days in Maui - the price is quite good compared to the normal resorts, you get a great view and anything you don’t pick up on your way from the airport you can grab on a 20 minute drive to Kihei. This place was perfect for us.
Waterfront apartment rentals

Stunning Beachfront - Hale Kai O Kihei 112
Everything was perfect and the location was great! It was nice to be just steps to the beach right in front of the condo. It was wonderful for my 2 little children. Robert is very attentive and helpful! I would stay again when I return.

Renovated 2BD/2BA | 3 Min Walk to Beach | A/C
Lovely and clean place, responsive host, and surprise additional beach equipment

Oceanfront Condo with a 5-star view!
We loved our stay! Communication with our host was fast and helpful, check in was easy and instructions great. Being able to see turtles from the balcony was a real treat, and having two bathrooms made it perfect for us as two couples. There were some lovely touches like beach chairs and a boogie board as well as beach towels - we really appreciated those - as well as essential supplies such as coffee and tea. Highly recommend!

Amazing Oceanfront Maui with A/C
There is no beach at this property. It is a rocky shore that is roped off with danger signs. The balcony is smaller than how it looks in the picture. Other than these two things. The property was very nice. Great A/C, clean with plenty of towels. It is also very close to the harbor where many activities can begin.

Oceanfront Condo. Pool & Spa, 1 Br.
Great location and unmatched views!

Remodeled Penthouse24 Ocean Front at Sugar Beach
Wonderful condo right on the beach with beautiful views of the Pacific; we could not count the number of whales we saw from the lanai. Having breakfast during sunrise ans dinner during sunset we’re one of the highlights of our days there. Can’t wait to come back.

Beachfront Penthouse #25 at Sugar Beach Resort
Chill location, swim-able beach, great sandwich shop / bar open till 10, great views, walkable to bakery, shaved ice, 10 minutes to local restaurants. Condo is well furnished and stocked for any type of stay.

Enjoy Ocean Views From Lanai, Living room & Bedroo
We had a lovely week long stay at this location. If you're looking for a well-kept Airbnb that's close to the beach then this is the place for you. The amenities were also great. We would absolutely stay here again.
Quick stats about waterfront rentals in Wailea, Wailea-Makena
Total rentals
270 properties
Nightly prices starting at
£90 before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
170 properties are a good fit for families
Rentals with a pool
260 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace
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