Vacation Rentals & Condos in Wailea

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175 condos

Wailea Ekolu 2/2 - Elegant, Spacious, Modern, Ocean View!

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$445

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Breachfront Oceanview King Bed Studio unit in Wailea Ekahi

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$344

MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • sleeps 6

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$496

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$802

Beautiful - Palms at Wailea 1802

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$487

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$286

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$1,088

Beautiful Remodeled 2 BR/2 BA Condo in Luxurious Maui Kamaole

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$447

Kamaole One

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$1,419

Unrivaled S Kihei Maui location! Walk to it all!

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$224

Gorgeous Ocean front view from your balcony! - Kihei Surfside #608

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$380

Spacious Ground Floor 1 Bedroom - Kihei Surfside #107

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$219

Stunning Oceanfront Condo - Kihei Surfside #511

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$239

Stunning Ocean Front Condo-Kihei Surfside #213

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$229

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$219

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Price per night from

$649

Beautiful Views Await You Here! - Kihei Surfside #305

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$229

Stunning Ground Floor 2 BDRM Condo WAILEA ELUA, #1403*

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$999

Garden Views & Gorgeous Interiors Await WAILEA ELUA, #0909*

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$349

Remodeled Mountain View 2 BDRM Condo - Royal Mauian #601

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$229

Luxurious Oceanfront Corner Unit SURF RESORT, #F-212

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing and Beautiful” Loved staying at this condo. Great accommodations, great services and support staff. The only odd thing was the power kept going out in the master bedroom/bathroom. Other than that, it was a 10!

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$869

Fantastic Location - Beautiful Condo -Makena Surf Resorts # G-204

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Maui memories” We were excited to be coming back back to Makena Surf after staying there two years ago and being so impressed with the unit and the beautiful surroundings back then. We were somewhat fearful that we could even come close to matching that same experience this time around, but this unit exceeded our expectations. We will be back in the near future.

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Price per night from

$699

Wailea Ekahi Ocean View 50A

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$395

Fully Remodeled Oceanfront Condo MAKENA SURF RESORT, #F-202

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$599

Beautiful Beach Front Luxury Corner Unit MAKENA SURF RESORT, #E-206

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic Stay at Makena Surf” We would definitely return to this property, if not exact condo, at Maken Surf. Great location and ideal building on the big beach.Make sure you see the development plan so you pick the right building - it's worth being beachfront. And when the west coast was in the clouds, we were always sunny. Lovely beach, quiet with just the right amount of action close by. Easy drive to area shops and restaurants. Condo was ideal and services were terrific. If you are looking for beach and pool bar, resort services - this is not your place. There is a beach and pool but no blended drinks being served. But you'll spend three times the money for a hotel room versus having the luxury of spreading out at "home" with your family for meals, movie night and morning breakfast on the lanai. A much nicer way to go and then eat dinner in all the great restaurants. Who wants to shower and dress for breakfast anyway? I'd rather eat on the lanai and relax. The condo has everything you would want for a lovely stay from good bedding, spacious bathrooms,beach chairs, daily maid service, to streaming Netflix and fully stocked kitchen. Rent a car and you are all set.You won't want to leave and you feel more like you live there rather than just being another tourist. Oh and having a washer dryer in the unit was super convenient. Overall... a lovely spot.

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Price per night from

$799

Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful week in paradise!” The staff at ali'i Resorts is fantastic and helped us to plan fun adventures for our family throughout our stay. The housekeeping staff was attentitive and worked hard each day to help make our stay great. The property and condo were both very well maintained and beautiful- with spectacular views throughout. One of our favorite features was the patio and the amazing view that we enjoyed while dining outdoors. The beach access was convenient, just a short walk down a paved path to the beach that offered kid friendly boogie boarding waves and rock outcropings for snorkeling. We have stayed in a few of the luxury hotels in Wailea and prefer the relaxed environment of Makena Surf.

1 of 2 match: Games room, Swimming pool

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Price per night from

$529

Great Location - Beautiful Grounds - 2 Bedroom Two Bath - Wailea Elua #2106

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Clean and spacious with attentive service” This is a nice condo rental for Wailea. While the furnishings and mattresses are not that up to date, the cleanliness and location are very good. I found the kitchen in particular to have very good supplies. When I complained about the terrible coffee maker, it was replaced immediately. I should have complained during our stay instead of afterwards, and we might have been able to make good coffee while there. The cleaning service was very good. I would have appreciated a second set of beach towels as one set is not nearly enough for a beach vacation. I also would say that the master bedroom mattress was not supportive and is probably too old. This unit is on the row closest to the road so if your 2nd bedroom sleepers are light ones, they might be bothered by traffic noise. Overall this is a great condo village to stay at, but these units are old and you are paying for proximity to the beach, not high end units.

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Price per night from

$429

Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful condo in Paradise!” Our stay at Ekahi Villiage 11F was nothing short of wonderful. The beautiful, well appointed condo is just a short walk to the pool pavilion and beach. We enjoyed many mornings sipping coffee on the well decorated Lani over looking the manicured grounds and ocean. We will be sure to book 11F again the next time we plan a trip to Maui!

Responds fast! avg. 1 hour 32 minutes

1 of 2 match: Games room, Swimming pool

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Price per night from

$974

Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-207

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Swimming pool

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Price per night from

$949

Beautifully Renovated 2 BDRM WAILEA ELUA, #2201

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Swimming pool

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Price per night from

$549

Lovely Ground Floor 2 BDRM Condo Wailea Elua Village # 105

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!!!” Our stay at Wailea Elua was absolutely great. Our accommodations were spacious and beautiful with a breathtaking view of the ocean. The grounds were remarkable with close access to beach and private sitting areas. The condo had everything you needed. The staff on hand were very accommodating. And close to shopping and restaurants.

1 of 2 match: Games room, Swimming pool

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Price per night from

$599

Stunning 1 Bedroom Wailea Condo Wailea Elua # 206

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Games room, Swimming pool

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Price per night from

$639

Classy 2 BD Condo W/ Excellent Amenities Wailea Elua Village # 1204

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“A Beautiful Unit” This unit has everything that a family of 4 needs to have a great vacation. Our boys loved the short walk to the ocean but were a little disappointed that there were no rackets for the paddle tennis court. The housekeepers were very helpful and security was very professional. We would be happy to rent this unit again.

1 of 2 match: Games room, Swimming pool

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Price per night from

$849

Gorgeous Ground Floor 1 Bedroom WAILEA ELUA, #2003

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“wonderful property, alii people very friendly and helpful” Was able to check in at 1:00 PM which was very helpful. The personnel from alii were, as usual very friendly and helpful. Condo comfortable and clean. Two bathrooms a good feature. Second year in this condo and reserved for next year.

1 of 2 match: Games room, Swimming pool

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Price per night from

$499

Beautiful Grounds with Ocean View WAILEA ELUA, #2101

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Vary nice” Accomodations were modern and clean. Resort is beautifully kept. I want to particualry praise the cleaning staff. The two women who came daily were amazing.

1 of 2 match: Games room, Swimming pool

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Price per night from

$369

Beautiful Wailea Condo Wailea Ekolu # 401

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Our Best Vacation to Date” We had a wonderful time in Maui and truly enjoyed our condo at Wailea Ekolu. The views of the ocean were amazing (whale watching from our lanai). We really appreciated that we were in a quiet location but still close to all the action. There were 4 adults and 2 children in the condo and we had plenty of room. Ali'i Resorts took care of us-we had a issue with the microwave not working on the first day and they had a replacement there within hours. The unit was very clean and the resort staff were always friendly and accommodating (whether it be answering questions about Maui or booking excursion or just bringing some extra toilet paper). We checked out other beaches but found ourselves always coming back to Wailea Beach- the best one for us- great snorkelling and waves for boogie boarding as well as easy access (about a 10-15 min walk from the condo). Can't wait to return.

1 of 2 match: Games room, Swimming pool

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Price per night from

$309

Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Games room, Swimming pool

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Price per night from

$349

Beautiful Beach Front 2 BDRM Condo - Makena Surf Resort # B-304

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Exquisite view, lovely appointments, needs new bed!” The good news: we only left this beautiful condo to jump into the water (in the ocean or the lovely pool), to go to yoga or for jogs, to get supplies or go out to eat! The view is stunning, the lanai couldn't be any closer to the water, has comfortable patio furniture and you have all the comforts of home. The kitchen and bathrooms are luxuriously appointed. After a slight confusion when we landed at the Kahului airport, we were even able to check in early on our arrival day. The only bad news, and the reason we couldn't give it five stars is the mattress in the master bedroom needs replacing. There are two huge, deep divots in the too-soft, too worn mattress. I hope that will be replaced soon, because when we come back to Makena Surf, we will definitely stay here. We've stayed in two other condos on the property, and this was the best!

1 of 2 match: Games room, Swimming pool

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Price per night from

$799

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