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Wailea Rentals

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Wailea Rentals

About Wailea

155 condos

Spacious and Elegant 2b/2B View Condo

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“A beautiful Condo and excellent Value!” This condo was newly renovated and from all of the units I looked at for rent in this complex, this one looks to be by far the nicest unit available. The unit was beautifully decorated and very well stocked with

$279

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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

$255

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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!!

$299

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

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$265

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

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$354

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Wailea Ekahi, Privacy and Luxury $149 - $265/nt May Special $139/nt

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 4

$149

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$295

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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

$159

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

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$249

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OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

Wailea cottage

1 bedroom / 2 bathrooms / Sleeps 3

“Excellent” We were sorry to leave, it had everything that we required for a perfect stay, we enjoyed breakfast on the lanai in the company of the friendly geckos, a beautiful view of the ocean, a comfortable bed, every appliance needed and very friend

Responds fast! avg. 2 hours 21 minutes

$169

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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

$275

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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

$1,497

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Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 Great Rates

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Two weeks in Paradise…” This was our third time on Maui and second time staying at Palms at Wailea. We love the location and ambiance of this condo complex, but the Unit #1508 definitely exceeded our expectation. It is a very nice and well-appointed u

$345

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Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$199

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

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$250

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Ekahi-2A Lower Village, Ocean Views and Sunsets

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Great unit in the best complex” An excellent unit: very clean, great layout, loads of space, well stocked kitchen amenities, and nice view. Its well situated close to one of the quiet pools and a short walk to the main pool and beach area. We love

$435

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Rainbow Deluxe

Wailea house

2 bedrooms / 2 bathrooms / Sleeps 4

“5 star review for Rainbow Deluxe” We just returned from a two week stay at this lovely cottage. The owners think of every detail from the welcoming treats to everything you could need to make your stay more comfortable. It genuinely feels like home a

Responds fast! avg. 2 hours 42 minutes

$249

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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

$225

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

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$225

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Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / Sleeps 8

$774

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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

$215

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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

$325

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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

$1,150

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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

$189

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Palms at Wailea #604 2/2 Great for 2 Couples Super Rates

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“As seen on the website” Unit 604 definitely met and surpassed our expectations. The booking process, checking in, and checking out were a breeze. We were a large group, with 3 units rented (from different companies) and ours was definitely the best de

$189

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Maui Ocean View, Ground Floor, Beach House Chic

Wailea villa

1 bedroom / 2 bathrooms / Sleeps 4

Responds fast! avg. 3 hours 35 minutes

$225

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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 =)

$199

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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

$425

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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 9 minutes

$190

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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

$199

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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

$174

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Wailea Elua #2110 - Gorgeous Ocean View 2B/2B

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 5

“Wailea Ocean Views” Gorgeous condo, amazing ocean views.

$395

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Beautiful Wailea Gem from $150

Wailea condo

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 3 hours 13 minutes

$150

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Wailea Ekahi Ocean View 50A

Wailea condo

1 bedroom / 2 bathrooms / Sleeps 4

$220

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

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 4

$225

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Palms at Wailea #1209 1 Bedroom 2 Bath Sleeps 4. Great Rates!

Wailea apartment

1 bedroom / 2 bathrooms / Sleeps 4

“Beatuful Remodel” The property is gorgeous, the rental process was easy and the complex is lushly landscaped.

$230

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Palms at Wailea 603 2bd 2ba Sleeps 6 Great Rates!!

Wailea apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Love Maui and the Palms” The Palms is our favourite place to stay in Maui. Room 603 was in very good shape but we had an incident the second to last day with water from the room above but the property management and rental management groups got on it

$199

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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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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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