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Waterfront holiday rentals in Wailea, Wailea-Makena
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Top-rated waterfront rentals in Wailea, Wailea-Makena
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Popular amenities for waterfront rentals in Wailea, Wailea-Makena
Waterfront apartment rentals
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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 🌺❤️
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Kauhale Makai - Oceanfront Property
We liked the place. It was clean, quiet, and located close to the beach. We had no issues and we felt like it was a nice stay. We would stay again.
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100 steps from the beach! Tranquil Seaside Oasis
Location is perfect. Amenities were perfect. Loved the balcony. Would definitely book here again. Very helpful host. Appreciated Revi and her excellent communication. It was nice to come back to the lovely home after a busy day of activities. 10/10.
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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.
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Sugar Beach Resort #532 - Maui HI
We have been coming to Sugar Beach annually since 2010. This condo has been remodeled recently so everything worked in it. The screen doors and sliding glass doors are in excellent shape, many condo units have poor ones so this was great to not have to fight with the doors. Kitchen was well equipped, portable fans were great to have.
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Next to Beach, Foods & Shops - Updated w/ View!
Very nice and clean place in a great location. Very close to a very nice beach, close to food and shopping Easy to find. Easy to go see other parts of the island. If you don’t want the beach the pool is there and nice. The beds are comfortable. Highly recommend it.
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Charley's Hideaway (Oceanfront)
What a wonderful location. Steps from the beach and plenty of local restaurants. Convenient to many sights and Derrick is generous with local history and facts. We highly recommend this rental.
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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 :)
Waterfront house rentals
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Brand Newly Remodeled Luxury 2 BR - Kapalua Golf
Really nice condo! Peaceful location and great view of the ocean and sunsets from the lanai. Easy walk to Kapalua Bay beach. Quick walk to the community pool. Our family enjoyed staying here! We will stay here again the next time we visit Maui.
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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.
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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!
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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!
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Centrally located and steps to the beach!
The flat was squeaky clean with everything (kitchen items) needed to “live” there for a week. About 100 feet from the beach and beautiful sunsets. Convenient to everywhere.
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Maalaea Kai 307 - Maui Prime Oceanfront
We spent a lovely three nights in this condo and it was perfect! We could not have asked for more. The view is just breathtaking, the beds were comfy, and the place was exactly what we’d hoped for. The location was wonderfully central for all our activities around the west side of the island. Our family, who was staying nearby was jealous they hadn’t booked this place, especially given it was more affordable than most. This place is an asset to any trip to Maui.
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Oceanview Penthouse and Beach Bliss!
This property exceeded our expectations. Location, views, beach equipment included to use. Everything about this unit made our experience great. Would definitely recommend.
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Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
Absolutely perfect! Beautiful beach access with great walkability to local restaurants and shops. This place was peaceful and quiet! Great sunset view from the balcony. The space was clean and very easy to find. The beach made for great turtle watching.
Waterfront apartment rentals
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Tonight is Reduced OceanFacing Maui Sunset resort
Nice clean space. Love the beach there. Get a hammock walk to the beach turn left and you will find a place to hang out.
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Renovated 2BD/2BA | 3 Min Walk to Beach | A/C
This was a great place to stay for a week. It is right across from a beautiful beach that we walked in the mornings and went to for amazing sunsets. There is a lot of activity going on around the area with restaurants, shopping and water activities. The unit is very comfortable for 4 people, may be tight with 2 more in the common space. The layout is nice, the kitchen is great and fully equipped, the beds were very comfortable. There is a nice balcony with a pretty view (not of the beach but still beautiful). The host was extremely responsive to questions and also reached out proactively to ask how things were going. Also the on island hosts were great. We had planned a surprise proposal on the trip and they helped with recommendations for photographers which worked out great. They were also responsive when we needed help with the television. My only critique is to add more closet/dresser space and for much bigger bath towels (we used the beach towels). It was a great stay!
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Valentines Specials! 2B/2B Direct Oceanfront, AC!
We have wonderful experience staying at Maui rental. The unit was waterfront and in great location to go around Maui. The hosts were very responsive and responded to any questions we had. Highly recommended!
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Oceanfront Condo. Pool & Spa, 1 Br.
My husband and I took a week away for the first time without our kids. This place was the best possible place for us. Close to everything we needed/wanted. The marina at the end of the road offered super fun things and the shopping center next to the marina offered food, shopping etc. (100% walkable) The bed was super comfortable and the amount of wildlife we saw daily in the ocean from the balcony was insane. Clean, had everything we needed. Only suggestion is a pair of scissors :) - would love to return and bring my kids on our next Maui vacation. Ron was great, contacted me a few days before, had great suggestions on a car rental place that saved us $ (that we pumped right back into the Maui economy) Couldn’t have asked for a better stay. Truly epic.
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Simply Amazing Oceanfront Condo! Milowai 310
Nice apartment with great view, without a car, not a lot to do but bus are convenient.
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Beachfront Penthouse #25 at Sugar Beach Resort
Our stay was amazing. Fit our family of four perfectly. Each day waking up to a beautiful sunrise and each night closing out the day with wonderful sunsets. Whales, dolphins, fish, and everything great about Maui either onsite or right down the road. Condo was perfect for us - pool, sauna, right on the beach, grill, nice kitchen, comfortable space. Thanks again for a great stay.
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Enjoy Ocean Views From Lanai, Living room & Bedroo
It was our first trip to Maui and it was absolutely wonderful. Our unit had partial ocean view with the balcony, a perfect spot for the morning coffee. The apartment is a little outdated but had basically everything you need to enjoy beach vacation including 4 beach chairs and umbrella, cooler and plenty of beach towels. The kitchen is well stock up. The only thing we would recommend is the small espresso machine for the espresso lovers like us to make it perfect. Thank you for amazing time at Maui!
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Stunning 5th Flr Oceanfront 2BR/2BA, AC, Renovated
My family and I really enjoyed the place, it was squeaky, clean and very spacious. Great views of the water from the patio. It was very much like the photos. You get reserved parking space. Super easy keyless entry to the condo is wonderful at any given time, not having to worry about key. The pool was a bit smaller than anticipated it’s still cute. Host is super responsive and attentive to any issues as we had a few minor ones. There was road construction noise and water outage for 1 day, but that was due to the city/county work happening on the street. Location is a bit remote, it’s more of a trip with residential buildings with walking distance things to do aside from the Starbucks and the Maui aquarium. However, I would say it’s a very central location to go to any direction around the island, which is absolutely perfect to go east west south north of the island and the airport/central shopping area is only 15 minute drive. Would definitely recommend staying here.
Quick stats about waterfront rentals in Wailea, Wailea-Makena
Total rentals
280 properties
Nightly prices starting at
£95 before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
180 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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