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Vacation Rentals & Condos in Wailea

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Vacation Rentals & Condos in Wailea

About Wailea

1,798 condos

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

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 5 minutes

1 / 49

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

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

1 / 47

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

1 / 34

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

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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

Responds fast! avg. 5 minutes

1 / 30

One-of-a-Kind Maui Getaway

Wailea house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 51 minutes

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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. 5 minutes

1 / 47

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

1 / 32

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. 5 minutes

1 / 35

OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

Wailea cottage

1 bedroom / 2 bathrooms / sleeps 3

Responds fast! avg. 2 hours 17 minutes

1 / 30

MAKENA SURF RESORT, #G-206^

Wailea apartment

2 bedrooms / / sleeps 4

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Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

1 / 27

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

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

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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

Responds fast! avg. 5 minutes

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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

Responds fast! avg. 5 minutes

1 / 39

Updated Spacious 3 Bdrm. Wailea Ocean View Condo

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

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

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 34 minutes

1 / 31
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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 4 minutes

1 / 15

New Listing Budget Vacation! Kihei Akahi C-616

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 / 24

WAILEA GRAND CHAMPION, #180^

Wailea apartment

3 bedrooms / / sleeps 6

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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

Responds fast! avg. 5 minutes

1 / 38

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

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

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Wailea Ekahi Ocean View 50A

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

1 / 17

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. 5 minutes

1 / 42

SPECIAL $270 a nt 10/21-10/30 5STAR REVIEWS GORGEOUS CONTEMPORARY GEM

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 6 minutes

1 / 25

WAILEA ELUA, #0105

Wailea apartment

2 bedrooms / / sleeps 6

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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. 5 minutes

1 / 41

Palms at Wailea #1501 Ocean View Inner Court Ground Floor 1Bd 1Ba Sleeps 4

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

1 / 24

Hale Makena Maui

Wailea villa

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 27 minutes

1 / 24

WAILEA ELUA, #1601*

Wailea apartment

1 bedroom / / sleeps 4

1 / 16

Book Early Save Big - 2019 14th Night FREE

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

1 / 44

MAKENA SURF RESORT, #G-204*^

Wailea apartment

2 bedrooms / / sleeps 5

1 / 16

WAILEA ELUA, #0202*

Wailea apartment

2 bedrooms / / sleeps 5

1 / 16

WAILEA ELUA, #0106

Wailea apartment

1 bedroom / / sleeps 2

1 / 16

Wailea Ekolu #105 2Bd/2Ba Scenic Ocean View Great Location, Full A/C Sleeps 4

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

1 / 36

Wailea Elua #2110 2Bd/2Ba, 2nd Flr Gorgeous Ocean View, Central Air, Sleeps 5

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 5 minutes

1 / 36
Viewing 38 of 1,798

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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