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Vacation Rentals & Condos in Wailea

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Vacation Rentals & Condos in Wailea

About Wailea

1,898 condos

One-of-a-Kind Maui Getaway

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 0 minutes

Price per night from

$1,500

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Sweeping Ocean Views; Private High End Condo!

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$199

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Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Exceeded Expectations” I love this property. We had looked at alot of places and time was running out. When this property popped up, I never thought it looked liked the way it did in person. It looked better in person. We are definitely returning. Mah

Responds fast! avg. 5 minutes

Price per night from

$159

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STOP! LOOK NO FURTHER! Palms at Wailea #1503 Ocean View Best Location!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

Price per night from

$360

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IS214 2 Bed, 2 Bath Large Ocean View Condo

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

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Updated Spacious 3 Bdrm. Wailea Ocean View Condo

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Great condo!” We absolutely loved the condo.  It was well appointed and spacious.  We hosted a gathering of about 20 people and the kitchen, dining, living spaces combined with the lanai comfortably held that many people. The location was perfect, ri

Responds fast! avg. 3 hours 50 minutes

Price per night from

$275

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New Listing Budget Vacation! Kihei Akahi C-616

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 27 minutes

Price per night from

$115

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Summer Special! Wailea Ekahi 46F- Spacious 2 bedroom 2 Bath Condo in Wailea!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great trip to Maui” My family and I enjoyed our time at Ekahi. Loved the view from the balconies, and chairs and other beach equipment was there for our use. The property management was very accomodating and when we had one thing missing from the cond

Price per night from

$295

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Wailea Ekolu #406 2 BD 2BA Panoramic Ocean View, Full A/C, Sleeps 4

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

Price per night from

$255

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Wailea Ekolu #201 Remodeled 2Bd/2Ba Oceanview Condo Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$250

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OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

Wailea cottage

1 bedroom / 2 bathrooms / sleeps 3

“Wonderful view and property” This was the perfect place for our annual stay on Maui. Dennis is the best host and takes care of any request you may have. The cottage is newly updated with all the conveniences and space needed. It is a very quiet are

Responds fast! avg. 2 hours 19 minutes

Price per night from

$249

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WAILEA ELUA, #2003

Wailea apartment

1 bedroom / / 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

Price per night from

$369

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Palms at Wailea #205 2B/2B - Luxurious, Spacious, Fantastic Location!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$225

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Wailea Ekolu #205 Ocean View, Ground Floor, Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$265

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Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd 2Bath Great Rates!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great Getaway!!” I loved unit 1105 at The Palms. It was totally updated and very clean. The beach chairs and boogie boards were nice to have. Loved the quiet nature of the Palms and the proximity to all of the beautiful beaches!!

Responds fast! avg. 5 minutes

Price per night from

$299

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AVAIL AUG 21-29 PEACEFUL 2BD2/BA REMODELED GRAND CHAMPION in Upscale WAILEA,

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful condo on the golf course” Our family of 4 - 2 kids ages 6 and 8 - had a wonderful vacation here in april. The condo is beautiful - well decorated, comfortable, comfortable beds, well appointed kitchen. The views from the back patio - Lan

Responds fast! avg. 3 hours 4 minutes

Price per night from

$279

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Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 31 minutes

Price per night from

$600

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Price per night from

$225

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Wailea Sunset Bungalow

Wailea house

2 bedrooms / 1 bathroom / sleeps 4

“Paradise at Wailea Sunset Bungalow” Our trip to Maui was fantastic, mostly due to the spectacular Wailea Sunset Bungalow. This home was stocked with absolutely everything a person or group could ever need for a week, even a month. We enjoyed the fam

Price per night from

$1,050

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Wailea Seashore Suite K507 at Wailea Beach Villas

Wailea house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$995

1 / 50

Wailea Ekolu #407 Completely Remodeled with Panoramic Ocean Views. Sleeps 2

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 2

“Saeed K.'s review of Wailea Ekolu Panoramic ocean views 1b/2b.” We loved the placed and everythign was great. It woudl have been much nicer to have the Wireless Internet workign though. ALso with an 11 night stay it would be nice to have at least one

Responds fast! avg. 5 minutes

Price per night from

$225

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Wailea Ekolu 805 Deluxe 2 Bd. 2 Bath, Ocean View Townhouse!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Ekolu Unit 805” Wailea Ekolu Unit 805 is a comfortable, clean, spacious, beautifully updated two bedroom/two bath condo. This first floor unit with a nice lanai has a partial view of the ocean and is located in a quiet area of the complex. I would not

Responds fast! avg. 5 minutes

Price per night from

$200

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Summer Special! Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Wailea Ekahi 48C” This condo is a bit dated. The bed was very comfortable. The showers weren't working well. Wailea Ekahi is a gorgeous setting. This unit is up the hill, a little walk from the beach and main pool. Wifi worked well which was key for m

Price per night from

$225

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INDO LOTUS BEACH HOUSE

Wailea apartment

4 bedrooms / / sleeps 8

Price per night from

$1,299

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Elua Village # 701 - Luxury 2b/2b with Ocean View!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Maui Magic” We have stayed in this unit twice and both stays were excellent! First, the location is awesome. A beautiful sandy beach is only a short walk away and what awaits you is fantastic snorkeling and scuba diving. In addition to the great divin

Price per night from

$425

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Great Ocean View Family Friendly GC#42

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$250

1 / 10

Maui Wailea Townhouse, 2BR, 2.5 Ba, air conditioned, sleeps 8, ocean view

Wailea apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 48 minutes

Price per night from

$190

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Regal Mandalay M511 Wailea Beach Villas

Wailea house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful place to stay” This was our second time in renting from Tropical Villa Vacations. They are always helpful with anything that we have asked. They had boogie boards ready for the boys at our condo when we arrived and they also found a place

Price per night from

$995

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5 Star Property across from Kihei's favorite beach

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$195

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Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Exceeded expectations by a mile!” From the moment we arrived we were amazed at the way the condos we rented (we had #48 as well) were decorated, furnished and stocked with anything we could possibly have wanted for our holiday. Even items for the beac

Responds fast! avg. 5 minutes

Price per night from

$174

1 / 30

Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great place to stay for the price” We loved the location and views from our units. The pool was warm and quite nice despite having many restrictions. The units were clean and nice looking however many of the amenities promised (ie. beach equipment) we

Responds fast! avg. 5 minutes

Price per night from

$295

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Price per night from

$294

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HALLOWEEN SPECIAL 10% OFF 10/21-10/30 5STAR REVIEWS GORGEOUS CONTEMPORARY GEM

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Happy with our stay” We enjoyed our stay. The location was very close to the beach and a pool, and there were chairs and gear we could use which was great. The room itself was quite nice and comfortable, including an excellent entertainment system and

Responds fast! avg. 3 hours 2 minutes

Price per night from

$225

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Palms at Wailea 609 Ground Level Garden View - 1Bd 2Ba Sleeps 4: Great Rates!

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

Price per night from

$200

1 / 35

Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Best experience ever in USA. Loved every minute of our stay.” #51 @ #48 condos were by far even better than the reviews and pictures described. My family from Canada and myself were truly impressed by the attention to detail and how well the units wer

Responds fast! avg. 5 minutes

Price per night from

$199

1 / 34

Grand Champion Villas, Where Happiness Lives!!

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Great home away from home” Bev and Tony's condo at Grand Champion Villas was everything that we expected and more. The condo was very comfortable, the directions for how to get there from the airport were very accurate and the condo had all the amenit

Price per night from

$275

1 / 20

Outstanding Luxury Condo for Couples in Paradise - Ocean and Beacfront

Wailea apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 59 minutes

Price per night from

$175

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Wailea Ocean View, 2Bed, 2Bath Beautiful Update

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

Price per night from

$240

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Viewing 38 of 1,898

About Wailea

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Famous for its five half-moon shaped beaches and world-class golf courses, Wailea is five times the size of Honolulu’s Waikiki with unmatched Pacific Ocean views. For a luxurious Hawaiian vacation in a very sought-after location, visit FlipKey where you will find a Wailea vacation rental to suit all your needs.

About Wailea

Wailea is located on the south-western part of Hawaiian Island of Maui, just 14 miles from Kahului Airport.

Meticulously laid out over 1,500 acres of lush tropical vegetation, the beach at Wailea is one of the most visited on Maui. The popularity of the beach is partly due to the area’s luxurious oceanfront resorts and spas, as well as its legendary year-round average temperature of 82 degrees!

Even the shopping at Wailea has an upmarket feel with Gucci, Louis Vuitton, Prada and Tiffany & Co all represented next to surfing boutiques such as Quicksilver, Rip Curl and the Honolulu Surfing Company.

When it comes to fine dining, you will be spoilt for choice with American, international and Hawaiian specialties all available.

Top Wailea events include the February Whale Week and the Maui Film Festival. See if you can catch one during your stay!

What to do

Avid golfers flock to Wailea just to play the Gold Course (one of the top golfing destinations in the country!). Robert Trent Jones II designed championship course that takes advantage of the natural surroundings, while incorporating stunning ocean views from every tee. A true thinking man’s course, and considered one of the best designed courses in the world.

Hawaii is, of course, all about surfing and Maui has its fair share of top spots where the pros come to catch big winter waves. But on the south of the island, the waves are around three feet in height, making them perfect for beginners.

Go hiking in the Haleakala National Park and climb to the top of the world’s largest dormant volcano, Haleakala, where you will be rewarded with fantastic views of the island.

Top Wailea travel tips

With almost perfect weather all year round, there is no bad time to visit Wailea.

For beach attire, avoid the fancy stores and ask the locals where they go shopping, instead. Consider buying a snorkel, mask, and fins as it can actually work out cheaper than renting.

Hawaii is a no-brainer for a tropical beach vacation, but with so many great amenities, Wailea truly is a world-class destination. To find your slice of paradise, FlipKey has dozens of Wailea vacation rentals to suit all budgets.

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