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Make a self catering villa or holiday rental in Wailea, Maui, Hawaii your home away from home

Wailea offers a wonderful destination for a relaxing, low-key vacation in the sun on Hawaii’s second largest island. Maui offers spectacular scenery, volcanoes, beautiful beaches and great shopping. Wailea is a relatively new resort but it is rapidly increasing in popularity. Popular as an idyllic wedding or honeymoon destination, a holiday villa in Wailea makes the perfect base for exploring the island’s natural beauty and lush vegetation. The island is known for its sugar plantations, pineapple farms and its exotic flowers. Although there are plenty of bars and restaurants close to Wailea, nightlife is fairly quiet.

Things to do in Wailea, Maui

Golf

Wailea is well-known for its beautifully maintained golf courses, each hole offering spectacular scenery and unique challenges.

Beaches and Watersports

Maui has some of the best beaches in the world along with clear warm seas. Relax in the sun, or take a snorkel and flippers and explore the fantastic underwater world. The area also offers excellent diving, including the offshore volcanic crater close to Wailea. Shopping

There are plenty of opportunities for shopping in and around Wailea. Lahaina Cannery Mall is in a replica canning factory and has 50 speciality shops and restaurants in a fun location.

Places to visit near Wailea, Maui Hana Highway

One of the world’s most scenic drives can easily be enjoyed from your Wailea apartment in Maui. The winding 56-mile tour takes in old plantation towns, beaches, forests and the Haleakala Crater. Lahaina

A traditional Hawaiian evening is guaranteed at the Lahaina Luau with a delicious buffet of local dishes such as kalua pig and haupia (coconut pudding) alongside international dishes. The outdoor beachside setting is fantastic and the local entertainment is colourful and vibrant. Enjoy the local cultural activities including Hawaiian music, hula girls and even fire dancing.

Pineapple Plantation Tour

Almost one third of the world’s pineapples come from Maui. See how pineapples grow, ride a cart, pick your own juicy pineapple and watch a pineapple cutting demonstration at one of the many pineapple plantations close to your holiday rental home in Waimea.

Weather in Wailea, Maui

Wailea is well known for its year-round tropical warmth. Temperatures range between 79-84°F (26-29°C) from winter to summer although Maui does have a little rain each month from October to March which falls as occasional showers. The mountainous inland region has heavy rainfall throughout the year.

Travel to Wailea, Maui

The main Maui airport serving your holiday home in Wailea is Kahului airport which receives both inter-island and overseas flights. It is approximately 25 miles from Wailea.

Honolulu International airport is on the nearby island of Honolulu so a connecting flight to Maui would be needed.

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Viewed 43 times in the last 48 hours
  • 3 BR Condo
  • 3 BA
Wonderful! 4.9/5
(56 reviews)
avg/night
56
Viewed 85 times in the last 48 hours
  • 1 BR Condo
  • 2 BA
  • 1022 sq ft
Exceptional! 5/5
(84 reviews)
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84
Viewed 75 times in the last 48 hours
  • 1 BR Condo
  • 2 BA
  • 866 sq ft
Wonderful! 4.8/5
(8 reviews)
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Premier Partner
8
Viewed 18 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
Wonderful! 4.9/5
(45 reviews)
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Premier Partner
45
Viewed 56 times in the last 48 hours
  • 3 BR Condo
  • 2 BA
  • 1700 sq ft
Wonderful! 4.9/5
(17 reviews)
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17
Viewed 64 times in the last 48 hours
  • 3 BR Townhome
  • 3 BA
  • Separate Toilet
  • 2426 sq ft
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Premier Partner
4
Viewed 31 times in the last 48 hours
  • 2 BR Townhome
  • 2 BA
  • 1500 sq ft
Excellent! 4.6/5
(5 reviews)
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Premier Partner
5
Viewed 38 times in the last 48 hours
  • 4 BR House
  • 2 BA
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Premier Partner
3
Viewed 15 times in the last 48 hours
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  • 2 BA
  • 1205 sq ft
Wonderful! 4.9/5
(10 reviews)
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Premier Partner
10
Viewed 33 times in the last 48 hours
  • 2 BR Cottage
  • 2 BA
  • 700 sq ft
Exceptional! 5/5
(22 reviews)
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22
Viewed 47 times in the last 48 hours
  • 2 BR Cottage
  • 2 BA
  • Separate Toilet
  • 700 sq ft
Exceptional! 5/5
(70 reviews)
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70
Viewed 24 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
Exceptional! 5/5
(46 reviews)
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Premier Partner
46
Viewed 41 times in the last 48 hours
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  • 2 BA
  • 1700 sq ft
Wonderful! 4.9/5
(59 reviews)
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59
Viewed 33 times in the last 48 hours
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  • 2 BA
  • 1845 sq ft
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Premier Partner
3
Viewed 42 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1505 sq ft
Exceptional! 5/5
(51 reviews)
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Premier Partner
51
Viewed 50 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 2200 sq ft
Wonderful! 4.9/5
(34 reviews)
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Premier Partner
34
Viewed 64 times in the last 48 hours
  • 3 BR Condo
  • 2 BA
  • 1383 sq ft
Exceptional! 5/5
(20 reviews)
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Premier Partner
20
Viewed 32 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1200 sq ft
Wonderful! 4.8/5
(10 reviews)
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Premier Partner
10
Viewed 38 times in the last 48 hours
  • 1 BR Condo
  • 2 BA
  • 908 sq ft
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Premier Partner
3
Viewed 5 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1353 sq ft
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Premier Partner
Viewed 26 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1350 sq ft
Exceptional! 5/5
(53 reviews)
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53
Viewed 62 times in the last 48 hours
  • 1 BR Condo
  • 2 BA
  • 1020 sq ft
Exceptional! 5/5
(3 reviews)
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Premier Partner
3
Viewed 8 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1194 sq ft
Excellent! 4.7/5
(28 reviews)
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Premier Partner
28
Viewed 49 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1194 sq ft
Excellent! 4.6/5
(48 reviews)
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Premier Partner
48
Viewed 32 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1200 sq ft
Wonderful! 4.9/5
(73 reviews)
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Premier Partner
73
Viewed 19 times in the last 48 hours
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  • 3 BA
  • Separate Toilet
  • 2900 sq ft
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1
Viewed 23 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1536 sq ft
Excellent! 4.6/5
(36 reviews)
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Premier Partner
36
Viewed 22 times in the last 48 hours
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  • 2 BA
  • 1180 sq ft
Wonderful! 4.9/5
(30 reviews)
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Premier Partner
30
Viewed 69 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1194 sq ft
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Viewed 82 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 2000 sq ft
Wonderful! 4.9/5
(64 reviews)
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Premier Partner
64
Viewed 91 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1186 sq ft
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Premier Partner
1
Viewed 39 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1100 sq ft
Wonderful! 4.9/5
(22 reviews)
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22
Viewed 81 times in the last 48 hours
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  • 2 BA
  • 2100 sq ft
Wonderful! 4.9/5
(28 reviews)
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Premier Partner
28
Viewed 82 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1200 sq ft
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Viewed 26 times in the last 48 hours
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  • 2 BA
Wonderful! 4.9/5
(23 reviews)
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Premier Partner
23
Viewed 86 times in the last 48 hours
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  • 1 BA
  • 792 sq ft
Wonderful! 4.8/5
(94 reviews)
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Premier Partner
94
Viewed 18 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1073 sq ft
Exceptional! 5/5
(26 reviews)
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26
Viewed 6 times in the last 48 hours
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  • 2 BA
  • 1505 sq ft
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Viewed 12 times in the last 48 hours
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  • 2 BA
  • 1700 sq ft
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Premier Partner
1
Viewed 17 times in the last 48 hours
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  • 2 BA
  • 1250 sq ft
Exceptional! 5/5
(109 reviews)
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109
Viewed 38 times in the last 48 hours
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  • 2 BA
Very Good! 4.1/5
(50 reviews)
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Premier Partner
50
Viewed 27 times in the last 48 hours
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  • 2 BA
  • 1070 sq ft
Excellent! 4.7/5
(9 reviews)
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Premier Partner
9
Viewed 39 times in the last 48 hours
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  • 2 BA
  • 1071 sq ft
Wonderful! 4.8/5
(26 reviews)
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Premier Partner
26
Viewed 14 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1070 sq ft
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Viewed 26 times in the last 48 hours
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  • 2 BA
  • 1100 sq ft
Excellent! 4.7/5
(21 reviews)
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Premier Partner
21
Viewed 15 times in the last 48 hours
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  • 2 BA
Exceptional! 5/5
(9 reviews)
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Premier Partner
9
Viewed 28 times in the last 48 hours
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  • 2 BA
avg/night
Premier Partner
Viewed 40 times in the last 48 hours
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  • 2 BA
Excellent! 4.5/5
(48 reviews)
avg/night
Premier Partner
48
Viewed 79 times in the last 48 hours
  • 1 BR Condo
  • 1 BA
  • 800 sq ft
Wonderful! 4.9/5
(20 reviews)
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Premier Partner
20
Viewed 12 times in the last 48 hours
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  • 2 BA
  • 1510 sq ft
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Premier Partner
3

Wailea Holiday Rentals & Homes (300+)