Vacation Rentals & Condos in Wailea

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SOUTH MAUI'S SPECTACULAR OCEANFRONT WAILEA SUNSET ESTATE WELCOMES YOU!

Wailea house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

“Truly Spectacular” This house is nothing short of spectacular. We chose this home for a family get-together and it worked perfectly. The Master Suite gave my husband and me the privacy we wanted, while our children and grandchildren had their own privacy. Each bedroom has its own bath. Everything was provided and ready for us upon arrival. We had T-times for golf, paddle boards, sea kayaks, snorkeling gear, as well as high chairs and cribs. Nothing was overlooked. We even took the opportunity to have a private chef (highly recommend just for the experience) cook dinner four different evenings, as well as adding on some additional cleaning. The sunsets were beautiful, the whales were breeching and the turtles surfed up to the rocky beach every night. Because of a tropical storm, we were able to watch professional surfers from our chairs on the grass. The larger hotels are within walking distance, but other than using the Spa facility at the Four Seasons, we felt no reason to leave this beautiful property. The management of Tropical Villa Vacations were extremely professional and easy to work with. For a group I would highly recommend this home. Everyone in our family had such a relaxing get-away that we plan to make this a bi-annual vacation and can't wait for 2016. There is nothing better than spending quality time with family, and this is the house to spend it in...truly spectacular!

Match: Jacuzzi or hot tub Private outdoor pool (unheated)

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Price per night from

$2,895

“The unit far exceeded out epectations!!” Th villa was as beautiful as presented on line. Very spacious and , well appointed. The kitchen featured high end appliances not normally seen in rental units. Beautiful decor. The owner has clearly put a lot of thought and resources into the comfort of his guests, right down to a fully stocked executive bar to every kitchen gadget you could possibly think of!!! The location was perfect. The unit was strategically located between the adults only and family pools... just s two minute walk to the beach. The concierge and rental agents were a pleasure to deal with and usually responded to any request within a hour. Great unit! Great experience!

Match: Jacuzzi or hot tub Private outdoor pool (unheated)

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Price per night from

$999

“Total luxury - we would definitely stay here again!” The villa itself (G102) was perfect. The finishings and furnishings are top quality. Much better than staying at one of the hotels. This villa is so spacious with the grass area and plunge pool. The beds are amazing!! Tropical villa vacations staff were so helpful and friendly, extremely professional. We would definitely recommend this villa.

Match: Jacuzzi or hot tub Private outdoor pool (unheated)

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Price per night from

$999

“A terrific experience.” The location and unit were perfect (except for the large sliding doors which never closed well.) We had little contact with your staff but what we had was great.

Match: Jacuzzi or hot tub Private outdoor pool (unheated)

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Price per night from

$1,199

ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Even more beautiful than the pictures.” We highly recommend Tropical Villa Vacations. Irene helped us find the perfect spot for our vaction. D101 is a beautiful addition to their inventory. The unit is spectacular. The Wailea Beach Villas property is a perfect spot for anyone looking for a luxurious condo in the heart of Wailea. Beautiful property, great ocean views and top notch service from a team that truly cares about your vacation experience!

Match: Jacuzzi or hot tub Private outdoor pool (unheated)

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Price per night from

$1,650

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WAILEA ELUA, #0702

Wailea apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$410

MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$498

2 Bedroom, 2 Bath Oceanview Penthouse Condo! Walk to the Beach!

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 16 minutes

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$286

Renovated Studio Steps from the Beach & Pool - A/C

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$229

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$689

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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$749

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$719

Beach Front Paradise -Remodeled 2 Bedroom Condo -Polo Beach Club #707

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$1,049

NEW! Modern 2bd/2ba Beach Retreat in Sunny Sout Kihei

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$378

Renovated 1BR at Maui Banyan - Pool, Hot Tub, A/C

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$286

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$679

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$1,062

Stunningly Remodeled 1 BDRM Wailea Elua #302

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$450

Completely Renovated, Ocean View, Steps To Beach WAILEA ELUA, #0908

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$701

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: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$851

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$641

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: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$751

Lovely Ground Floor Unit MAKENA SURF RESORT, #C-102

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$641

Gorgeous Beach Front Condo MAKENA SURF RESORT, #E-202

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$721

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!

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$871

Stunning Condo on the Golf Course - WAILEA GRAND CHAMPION #90

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$299

Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$219

Beautiful Golf & Ocean Views - WAILEA GRAND CHAMPION #148

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$229

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: Private outdoor pool (unheated), Jacuzzi or hot tub

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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: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$529

Spectacular Ground Floor 2 Bedroom Condo Wailea Elua #305

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$489

Stunning Ground Floor 2 Bedroom Wailea Elua #307

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$449

Prime Wailea 2 BDRM Condo Wailea Elua Village # 801

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$649

Beautiful Ocean Views - Wailea Elua Village #802

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$519

Beautiful Ground Floor 1 Bed/2 bath WAILEA ELUA, #807

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$349

Beautiful & Spacious Ocean View Condo WAILEA ELUA, #0902

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

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Price per night from

$699

Spacious Wailea Condo-Ocean Views-2 BDRM Condo Wailea Elua #1104

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$699

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

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$999

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