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

Pele’s Penthouse Top Floor Book Now!
The first morning we sat out on lanai and we're able to spot some whales. Beautiful view of ocean and quiet kid friendly beach right next door. 2 bathrooms and 2 bedrooms exactly as pictured. Had all we'd need to stay. I would recommend bringing your own toiletries as they provide hotel size 2 in 1 for hair and no body wash just bars of soap. the beach towels, beach sand toys, and beach chairs we super nice to have that they have out on lanai. it was very clean and comfortable and a great central location to many food places, fruit markets and beaches. I recommend getting fruit shave from Gus's and Ulalanis shave ice. Also malasadas (donuts) fresh were divine. found them at food trucks and the shops at wailea the grocery market there. such a memorable trip as a family! thank you for letting us make your place our home for the week. Mahalo 🌺❤️

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

100 steps from the beach! Tranquil Seaside Oasis
I stayed in this apartment for two days. Very nice, clean and cozy apartment. No cockroaches and ants because I'm usually afraid of them, but the accommodation was very clean. Thanks to the owner of the house for always being in touch and allowing me to check in a little earlier. Overall, everything is good, I would come back here again!

Maui Calling! Oceanfront Condo with Amazing Views.
We booked Loren's place back in June for our December trip and I believe it was a brand new listing, so we were hoping that the pictures and description matched...and I can tell you the pics don't do it justice. We stayed Dec 25-31, just my wife and me. We typically have stayed in Kaanapali Shores in the past, so this was our first time at Sugar Beach Resort. I think we found our new favorite place to stay. Our first morning we saw several pods of whales putting on a show...all from the comfort of our balcony. The unit itself is perfect for two people and had everything we needed with a well appointed kitchen. Dina's Sand Witch shop was also great and is a local hangout...so you know it is good. Overall, a great trip. And the secret is out about this unit, as the rates increased since our booking...but I think it was somewhat under priced when we originally booked it.

Scenic Paradise: Maui 1BR Haven.
This was a real gem of a find! We loved our stay here the hotel apartment was massive clean great views host was really helpful and clear! Kids loved the pool and use of facilities like staying in a hotel!

Sugar Beach Resort #532 - Maui HI
The condo was in a nice area, fairly central to everything with a bakery, farmers market, and small store within walking distance. The view is beach front, 5 stories up, and we enjoyed sitting on the balcony watching for whales, rowers, and beach activity. We used the grill area, which was kept very clean, by the pool and hot tub on the condo grounds. The kitchen seemed to have all the amenities we needed to prepare a few small meals. We had a great stay in Maui!

Beautiful Oceanfront Condo
Had a wonderful few days in Maui and Brooke’s apartment was a great place to stay! Such a central location, and easy to find, with local shops and stalls, places to eat (the food trucks right behind were a perk!) and a stunning view across to the beach to enjoy, especially the sunsets - beautiful! Everything was within walking distance, however having a car to explore the island more was essential and parking was super easy! Brooke was really helpful and responsive to messages and the apartment is tidy with everything you need :)

Wailea Couples Retreat, 300 FT To Keawakapu Beach
Perfect distance to the beach and other amenities, room fit 2 comfortably, kitchen was great making it an easy stay. Condos were beautifully landscaped and held amazing views! We had a great access to the private beach and the condo was close to other great beaches! It is located within the lush area of Wailea, very close to Kihei, where there are plenty of things to do! We loved every minute of our trip and our stay was problem free. Thank you!!
Waterfront house rentals

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!
We had a great stay at Ashley and Mike’s! Lots of great food places and grocery stores/ coffee shops within quick walking distance. We utilized the provided beach chairs, coolers and umbrella pretty much daily. Ashley and Mike were easy to communicate with. The place was super clean and comfortable. We would definitely return :)

Maalaea Kai 307 - Maui Prime Oceanfront
Great place in a great location. 15 minute drive from the airport, cute area, reasonable drives to all of the places we went (Road to Hana, Kaanapali, Ioa Valley). My family of 4 were very happy there! We saw whales from our lanai several times. Great trip!

Come Back to Puamana Nani
Annie is a great host, the home was clean and comfortable. The beach a minute or two walk. The pool is close to the condo, about a minute too. We slept peacefully in the comfortable beds, the kitchen was well stocked, and the place is beautiful and comforting. We sat outside to drink coffee in the mornings and it felt like home, but better.

Aloha Aku Hula Suite – Find Peace by the Shore
Location was ideal! Right on the beach, access to a small shared pool and hot tub, made it feel like your own private beach house. Kayaks and paddle boards were readily accessible, and were able to launch them right from the yard. We would not hesitate to stay here again.
Waterfront condo rentals

Renovated 2BD/2BA | 3 Min Walk to Beach | A/C
Excellent Airbnb location to what we were looking for. Even had beach accessories that came in handy. Place had AC in each room which was nice as well.

Direct Oceanfront 2B/2B ~ Maalaea Banyans 409
The location was GREAT - close to many activities/places and the ocean-front was consistently beautiful! We saw turtles swimming and beached every day and a few whales blowing from afar every morning. We traveled with 2 kids (age 11 & 9) and a grandpa in his 70's. Air conditioning was not a problem - there were many fans provided and the ocean breeze was perfect. I truly appreciated the beach supplies (beach towels, sand toys, chairs, large umbrellas, 2 boogie boards, cooler, and extra snorkel items), a fully stocked kitchen, and a generous supply of everyday items (soap, toilet paper, etc) that some AirBnBs don't normally supply enough of. I would have preferred the bathrooms and balcony to be slightly cleaner, but definitely not a deal breaker. Advance notice about the elevator not working would have been appreciated (thankfully we were physically able to climb 4 floors of stairs multiple times a day, and with large luggage). Overall, would recommend to others!

Oceanfront Condo. Pool & Spa, 1 Br.
This was the absolute perfect spot! Peaceful but still fun!

Simply Amazing Oceanfront Condo! Milowai 310
This unit was fantastic. we enjoyed our stay very much

Beachfront Penthouse #25 at Sugar Beach Resort
Beautiful view from the lanai. Peaceful and quiet Spent a lot of time on the lanai. Equipped with everything you need.

Oceanfront Oasis of your Dreams
Kazia’s place was beautiful. It was walking distance to some of the activities we did (whale watching, haven’s restaurant) and was centrally located to everything else on the island we explored. I could have sat on the balcony all day - it was so relaxing. I would definitely stay here again. Kazia was also very responsive and made the check-in and check-out process so easy! The place was stocked with everything we could’ve needed (snorkel gear, sunscreen, aloe, etc). Overall, it was an amazing trip and I’m thankful for Kazia’s accommodations and hospitality.

Stunning 5th Flr Oceanfront 2BR/2BA, AC, Renovated
This is a great condo in a great area of resort condominiums, just a short walk to the Maui Ocean Center aquarium and Ma'alea harbor. The grounds and building are well maintained and accessible with an assigned parking space. The accommodations were clean and tidy, with many thoughtful touches for our arrival. AC units in each bedroom and the living room ensured comfortable days and nights as needed. Beds and linens were super. The balcony faces southwest, has a partial ocean view, and overlooks the pool area. Patio table and chairs allowed wonderful breakfasts enjoying the boats in the bay. Our host was in communication from the time we booked to our departure, and was quick to respond to texts. The location made it easy to access Maui sites and attractions via rental car. We took advantage of the host-supplied beach chairs (4) and cooler for our day-long adventures. We would recommend!

Oceanfront Modern 3 Bed Loft - Near Maalaea Harbor
The condo is outstanding - with a master bedroom, a loft bedroom and a small third bedroom, plus two full bathrooms. The kitchen and bathrooms were spotless and well equipped. The balcony was incredible - great views of the ocean (which is literally steps away) to watch sea turtles frolic and palm trees blow in the wind. There were even occasionally whales (albeit far out). There is a beautiful lawn and a smallish pool and hot tub which the kids had a blast in. The location is great to access any beach or activity on the island within an hour drive (most much less), and it was a short walk to Maui harbor shops with the marina and a few restaurants and stores. In the other directions, it’s a 5 min walk to the end of sugar beach which is beautiful and secluded. Outside of Melanie’s control, the building elevator was down, though we were very fairly compensated for this inconvenience. Melanie was kind, professional and promptly responsive. We would stay here again without a doubt.
Quick stats about waterfront rentals in Wailea, Wailea-Makena
Total rentals
270 properties
Nightly prices starting at
ﺩ.ﺇ588 before taxes and fees
Total number of reviews
5.3K reviews
Family-friendly rentals
170 properties are a good fit for families
Rentals with a pool
270 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace
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- Sandy Beach
- Laie
- Kaipukaihina
- Wailea Beach
- Oneloa Beach
- Hāmoa Beach
- Ka'anapali Golf Courses
- Maui Ocean Center
- Pahoa Beach
- Honukanaenae
- Kanaio Beach
- Changs Beach
- Kaulana Beach
- Oneuli Beach
- Waipu
- Puu Olai Beach
- Maluaka Beach
- Mokulau Beach
- Wailea Golf Club
- Kaleʻia
- Pepeiaolepo Beach
- Palauea Beach
- Mōkapu Beach
- Kapueokahi Beach