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Vacation Rentals & Condos in Wailea

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Vacation Rentals & Condos in Wailea

About Wailea

1,880 condos

One-of-a-Kind Maui Getaway!

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 51 minutes

Price per night from

$1,507

1 / 28

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 10 minutes

Price per night from

$286

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Wailea Ekolu 805 Deluxe 2Bd/2Ba, Ocean View Townhouse! Full A/C, Sleeps 4

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. 26 minutes

Price per night from

$215

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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. 3 hours 7 minutes

Price per night from

$190

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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

$196

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$255

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Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4

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. 26 minutes

Price per night from

$299

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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. 26 minutes

Price per night from

$174

1 / 30

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. 26 minutes

Price per night from

$159

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Wailea Ekolu #205 2Bd/2Ba Ocean View, Ground Floor, Near Beach, Wifi Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$265

1 / 46

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$698

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Wailea Ekolu #201 2Bd/2Ba Ocean View Condo Near Beach, A/C, Wifi, Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$250

1 / 34

Palms at Wailea Unit #2305 1Bd/2Ba Quiet, Very Private! Near Beach, Sleeps 2

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. 26 minutes

Price per night from

$189

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New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$698

1 / 33

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

Price per night from

$1,150

1 / 21

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. 26 minutes

Price per night from

$199

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Price per night from

$551

1 / 23

Just Renovated 3bd 3ba in South Kihei, Hawaii

Wailea condo

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$498

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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. 26 minutes

Price per night from

$199

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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. 26 minutes

Price per night from

$295

1 / 38

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

1 / 21

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

1 / 25

Prime Beachfront, Polo Beach Wailea/Makena #204 - Accommodates 1-6, Free Wifi

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“One of the finest vacation stays in Hawaii!” We have been travelling to Wailea since the early 1980's and always stayed just north of the Polo Club in other condos. The Polo Club locale, just off the beach, beautifully furnished, well maintained and

Responds fast! avg. 1 hour 20 minutes

Price per night from

$498

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Wailea Ekahi Ocean View 50A

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$221

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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

$302

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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. 34 minutes

Price per night from

$169

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Wailea Elua Village # 2107

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Maui Wailea Elua 2107” Very nice, comfortable 2 BR condo. In the upper tier of buildings in the development, so short walk down the hill to the beachwalk. Though nearer to the road, no noise in unit. Has a front lanai facing the ocean, landscaped b

Price per night from

$411

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Palms at Wailea 702 Upstairs Garden View 1Bd/2Ba, Great Rates! Sleeps 4

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Great Stay in #702” The unit was very spacious, very clean(the carpet had just been steam cleaned before we arrived) and is in great location in Wailea which is in the quieter part of Kihei. The lanai was large and perfect to spend the evening sipping

Responds fast! avg. 26 minutes

Price per night from

$169

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SPECIAL $270 a nt 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 6 minutes

Price per night from

$251

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Price per night from

$150

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Palms at Wailea #205, 2Bd/2Ba, Luxurious, Spacious, Fantastic Location!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$289

1 / 26

Wailea Elua Village #4C

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

“Pleasant” Though I was told that this was going to be on the beach. Not quite - but not a far walk either. Very good for couples but not so good for families. Some of the older folk looked at the kids and were not smiling :-( Very nice unit that

Price per night from

$236

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The Palms at Wailea 901 - Luxury Privacy & Beaches

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$190

1 / 21

Book Early Save Big - 2019 10th Night FREE

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$196

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Grand Champions # 180

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

“A little piece of paradise!” Our family loved our stay! The kids enjoyed the pools and we loved our ocean view. We even loved the birds who woke us up each morning. We did the short drive down to Big Beach and ahihi Cove, we also walked down to Uluu

Price per night from

$251

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STOP! LOOK NO FURTHER! Palms at Wailea #1503 2Bd Ocean View Best Location!

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$360

1 / 41

Ho'Olei Largest Floor Plan - Ocean and Pool Views

Wailea house

3 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$1,445

1 / 22

New Listing Budget Vacation! Kihei Akahi C-616

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$135

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Viewing 38 of 1,880

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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