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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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  • 2 BR Condo
  • 2 BA
  • 1194 sq ft
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(29 reviews)
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  • 3 BA
  • 1550 sq ft
Wonderful! 4.8/5
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44
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  • 1200 sq ft
Excellent! 4.6/5
(36 reviews)
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36
  • 1 BR Condo
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  • 1280 sq ft
Wonderful! 4.9/5
(39 reviews)
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39
  • 3 BR Condo
  • 3 BA
Wonderful! 4.9/5
(58 reviews)
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  • 1 BR Condo
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  • 900 sq ft
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Viewed 7 times in the last 48 hours
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  • 1071 sq ft
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29
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  • 1072 sq ft
Exceptional! 5/5
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  • 1039 sq ft
Exceptional! 5/5
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5
  • 2 BR Condo
  • 2 BA
  • Separate Toilet
  • 1489 sq ft
Wonderful! 4.8/5
(51 reviews)
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51
  • 2 BR Condo
  • 2 BA
  • 1505 sq ft
Exceptional! 5/5
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52
Viewed 5 times in the last 48 hours
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  • 2 BA
  • 1090 sq ft
Exceptional! 5/5
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53
  • 2 BR Townhome
  • 2 BA
  • 1500 sq ft
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  • 1038 sq ft
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39
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  • Separate Toilet
  • 700 sq ft
Exceptional! 5/5
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76
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  • 1 BR Condo
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  • 866 sq ft
Wonderful! 4.9/5
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38
  • 2 BR Condo
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  • 1700 sq ft
Wonderful! 4.9/5
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60
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  • 1156 sq ft
Wonderful! 4.9/5
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56
  • 1 BR Condo
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  • 1180 sq ft
Wonderful! 4.9/5
(33 reviews)
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  • 818 sq ft
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Viewed 5 times in the last 48 hours
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Wonderful! 4.9/5
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46
  • 1 BR Condo
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  • 1168 sq ft
Exceptional! 5/5
(7 reviews)
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  • 1 BR Condo
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  • 1022 sq ft
Excellent! 4.4/5
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11
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  • 1 BR Condo
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  • 900 sq ft
Excellent! 4.7/5
(21 reviews)
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21
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  • 2 BA
  • 2100 sq ft
Wonderful! 4.9/5
(29 reviews)
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  • Studio
  • 1 BA
Wonderful! 4.8/5
(52 reviews)
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52
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Excellent! 4.6/5
(10 reviews)
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10
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  • Separate Toilet
Excellent! 4.5/5
(24 reviews)
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24
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Exceptional! 5/5
(61 reviews)
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61
Viewed 8 times in the last 48 hours
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  • 3 BA
  • 1500 sq ft
Wonderful! 4.8/5
(18 reviews)
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18
Viewed 7 times in the last 48 hours
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Exceptional! 5/5
(5 reviews)
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5
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  • 2 BA
  • Separate Toilet
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1
  • 1 BR Condo
  • 2 BA
  • 950 sq ft
Exceptional! 5/5
(21 reviews)
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21
  • 2 BR Condo
  • 2 BA
  • 1194 sq ft
Excellent! 4.5/5
(33 reviews)
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Premier Partner
33
  • 1 BR Condo
  • 2 BA
Wonderful! 4.9/5
(24 reviews)
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Premier Partner
24
  • 1 BR Villa
  • 2 BA
  • 908 sq ft
Wonderful! 4.9/5
(24 reviews)
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24
Viewed 10 times in the last 48 hours
  • 3 BR Townhome
  • 3 BA
  • Separate Toilet
  • 2426 sq ft
Exceptional! 5/5
(6 reviews)
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Premier Partner
6
Viewed 7 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1250 sq ft
Exceptional! 5/5
(112 reviews)
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112
Viewed 11 times in the last 48 hours
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  • 2 BA
  • 885 sq ft
Wonderful! 4.8/5
(6 reviews)
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Premier Partner
6
Viewed 9 times in the last 48 hours
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  • 1148 sq ft
Wonderful! 4.9/5
(59 reviews)
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59
Viewed 11 times in the last 48 hours
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Wonderful! 4.9/5
(27 reviews)
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Premier Partner
27
Viewed 7 times in the last 48 hours
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  • 818 sq ft
Excellent! 4.4/5
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60
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Exceptional! 5/5
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5
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(11 reviews)
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11
Viewed 8 times in the last 48 hours
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  • 1100 sq ft
Wonderful! 4.9/5
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21
  • 2 BR Condo
  • 2 BA
  • 1350 sq ft
Exceptional! 5/5
(54 reviews)
avg/night
54
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  • 2 BA
  • 1100 sq ft
Exceptional! 5/5
(40 reviews)
avg/night
40
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  • 1098 sq ft
Wonderful! 4.9/5
(50 reviews)
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Premier Partner
50
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  • 1 BA
  • 800 sq ft
Wonderful! 4.9/5
(24 reviews)
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Premier Partner
24
  • 1 BR Condo
  • 2 BA
  • 969 sq ft
Exceptional! 5/5
(32 reviews)
avg/night
Premier Partner
32

Wailea Holiday Rentals & Homes (300+)