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Wailea Rentals

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Wailea Rentals

About Wailea

224 condos

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

$274

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One-of-a-Kind Maui Getaway

Wailea house

4 bedrooms / 4 bathrooms / Sleeps 10

Responds fast! avg. 3 hours 9 minutes

$1,495

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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. 2 hours 15 minutes

$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. 2 hours 15 minutes

$250

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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. 2 hours 15 minutes

$159

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

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 2 hours 15 minutes

$265

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Responds fast! avg. 2 hours 54 minutes

$110

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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. 2 hours 15 minutes

$225

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WAILEA EKOLU, #312

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 2

$149

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Wailea Ekolu #105 Scenic Ocean View, Great Location, Sleeps 4

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 2 hours 15 minutes

$249

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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. 2 hours 15 minutes

$199

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Palms at Wailea Unit #2305 Quiet and Very Private!

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 2

“Great for Couples” For those of us who hate living in hotels, or paying for services we don't use, this 1 bedroom/2 bathroom condo is perfect. It feels and looks even larger than the photos and is equipped with a full kitchen, that is very well stocke

Responds fast! avg. 2 hours 15 minutes

$179

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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. 2 hours 15 minutes

$225

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Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba

Wailea villa

3 bedrooms / 3 bathrooms / Sleeps 8

“Wonderful stay in the Penthouse Villa...” Service: 5 Stars - The owner was very prompt in replying to email with questions, concerns. Concierge and front desk staff were courteous and very helpful. The bellman/staff even brought all of our luggage

$1,146

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Blue Horizons K308 Wailea Beach Villas

Wailea villa

4 bedrooms / 3 bathrooms / Sleeps 8

“It could not have been better.” From the minute we pulled up to the door in our car to the minute we left, everything was absolutely first rate. We so appreciated the gentleman who hauled all of our groceries from the car to our room when we were so t

$1,495

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Grand Champions #143 is a 3Bd/2Ba golf course view condo, sleeps 8

Wailea apartment

3 bedrooms / 2 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 15 minutes

$325

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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. 2 hours 15 minutes

$299

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$548

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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. 2 hours 15 minutes

$295

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Wailea Ehaki 20F - 2min Walk to Beach, Ocean Views

Wailea condo

2 bedrooms / 2 bathrooms / Sleeps 6

$424

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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. 2 hours 15 minutes

$215

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IS214 2 Bed, 2 Bath Large Ocean View Condo

Wailea condo

2 bedrooms / 2 bathrooms / Sleeps 6

$175

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The Perfect Location for a Relaxing Hawaiian Getaway - Grand Champions #103

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 4

“This is a beautiful condo, wonderfully maintained, in a great lo” We have stayed at many condos on Maui for years, and this is absolutely our favorite. We were lucky enough to be the first guests, and everything was even better than expected. The pho

Responds fast! avg. 48 minutes

$169

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Beautiful Wailea Gem from $150

Wailea condo

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 3 hours 47 minutes

$150

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$294

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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. 2 hours 15 minutes

$174

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Maui Ocean View, Ground Floor, Beach House Chic

Wailea villa

1 bedroom / 2 bathrooms / Sleeps 4

Responds fast! avg. 2 hours 44 minutes

$225

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Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / Sleeps 8

$598

1 / 32

Sun Splash C301 Wailea Beach Villas

Wailea house

3 bedrooms / 4 bathrooms / Sleeps 6

“Very Impressive and I am hard to impress!!” Our stay at the Wailea Beach Villas was absolutely amazing! A typical vacation for us in the last few years has been atlantis Royal Towers Bahamas, Westins ,Fairmonts and Grand California resort at Disneyla

$1,595

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WAILEA ELUA, #2204*

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$490

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Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 6.

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Loved it” Loved the area the condo was located. Very clean, and spacious. Kids loved the pool =)

Responds fast! avg. 2 hours 15 minutes

$199

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Summer Sale - 10th Night FREE !!!

Wailea condo

2 bedrooms / 2 bathrooms / Sleeps 6

$195

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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. 2 hours 15 minutes

$354

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WAILEA ELUA, #1305^

Wailea apartment

3 bedrooms / 3 bathrooms / Sleeps 6

“Great location!” We really enjoyed our stay at Elua Village 1305. The proximity to the beach was outstanding as was the sunsets each and every night. Three beds and baths with 6 people make life very comfortable. The unit could use some updates such

$1,216

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LUXURY FOR LESS! Best value in Hoolei Wailea!

Wailea villa

3 bedrooms / 4 bathrooms / Sleeps 8

$1,100

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Wailea Ekolu #804 Best Panoramic Ocean View 1Bd 2Ba Private location!

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 4

Responds fast! avg. 2 hours 15 minutes

$225

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Aqua Lani J305 Wailea Beach Villas

Wailea villa

3 bedrooms / 3 bathrooms / Sleeps 6

“Beautiful condo in Wailea!” A wonderful condo with 3 bedrooms & 3 bathrooms for six adults that was decorated with a modern touch & clean facilities. The beach is walking distance & the private pool very relaxing (separate kids pool area); didn't take

$1,045

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SPRING SPECIAL $189 a nt 4/24-4/28 5 STAR reviews GORGEOUS Palms at Wailea 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

$225

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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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