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Condos and resorts Maui/Wailea

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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 222 Rentals in Wailea
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$169
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
22 photos Details
Reviews (14) Make Enquiry
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$169
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (17) Make Enquiry
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$631
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Reviews (9) Make Enquiry
Also consider
Stylish Renovated Modern with Large Private Lanai!
2 Bedrooms, sleeps 6
$196 - $265 / night
Awesome Ocean View - Beautiful 2 BR Maui Condo
2 Bedrooms, sleeps 6
$398 - $525 / night
Luxury Wailea Beach Villa great price! From $725!
2 Bedrooms, sleeps 6
$769 - $1,325 / night
Totally renovated, closest to the beach!
1 Bedroom, sleeps 5
$265 - $371 / night
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$117
Per Night
Studio, 1 Bathroom, Sleeps 2
14 photos Details
Reviews (21) Make Enquiry
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$211
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
50 photos Details
Reviews (6) Make Enquiry
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$200
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
49 photos Details
Reviews (33) Make Enquiry
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$184
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
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From
$190
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
27 photos Details
Reviews (23) Make Enquiry
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From
$1,907
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
83 photos Details
Reviews (5) Make Enquiry
From
$180
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
23 photos Details
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$1,161
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
75 photos Details
Reviews (1) Make Enquiry
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$953
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
65 photos Details
Reviews (10) Make Enquiry
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$313
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
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From
$265
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (13) Make Enquiry
From
$363
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
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$363
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
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$190
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
30 photos Details
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From
$267
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
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$254
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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$244
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
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$424
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
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$264
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (34) Make Enquiry
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$138
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
25 photos Details
Reviews (19) Make Enquiry
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$292
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
18 photos Details
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$1,797
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
81 photos Details
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$254
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
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$1,373
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
73 photos Details
Reviews (10) Make Enquiry
From
$429
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (16) Make Enquiry
From
$211
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (16) Make Enquiry
From
$105
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (7) Make Enquiry
From
$424
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (9) Make Enquiry
From
$169
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (1) Make Enquiry
From
$466
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (6) Make Enquiry
From
$190
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (5) Make Enquiry
From
$358
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (15) Make Enquiry
From
$292
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
17 photos Details
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From
$212
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
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From
$366
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
38 photos Details
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From
$265
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
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From
$6,345
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Reviews (5) Make Enquiry
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Book Online(69)
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Suitability

  • Wheelchair access (15)
  • Elder access (61)
  • Suitable for children (54)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Internet (204)
  • Grill (181)
  • Air Conditioning (157)
  • All pools (154)
  • Public pool (147)
  • View all amenities
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Wailea Holiday Rentals

If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.

Things to do in Wailea

Obviously you will be wanting to hit the beach in Hawaii, and there are many from which you can choose, such as Keawakapu Beach, surrounded by golf courses. If you don't want to spend all your time lying on one of the many south-facing beaches but aren't quite brave enough to go and climb a volcano, Wailea has many things to do for all ages, from playing golf and tennis to the inevitable shops and restaurants, all in an incredible Pacific climate. Wailea is fairly sparsely populated, with around 6,000 inhabitants, so you can also have a great time exploring the countryside nearby.

Renting villas and condos in Wailea

Wailea Resort is a wonderful place to visit and stay, but its planning is a bit contrived - the Wailea Community Association issue guidelines for new buildings aiming to preserve the island feel of Maui. With the additional aim of low population density, this does mean that prices even for holiday rentals may be higher than in other parts of the Hawaii island chain. But with the scary prices charged by hotels, and the extra flexibility associated with renting your own villa or condo for your family, Wailea holiday rentals still represent fantastic value for money. With air conditioning thankfully coming as virtually standard, and difficult choices of whether you'd prefer views of a volcano, a golf course, or perhaps a beach, it's an idyllic place to enjoy a great family holiday. And if you are looking for a low cost Pacific break, nothing beats buying local produce and cooking it up in your very own kitchen for the week, rather than relying on a hotel's expensive restaurants.