We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Condos and resorts Maui/Wailea

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 222 Rentals in Wailea
loading...
Sort by
From
$466
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (8) Make Enquiry
From
$211
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
Reviews (18) Make Enquiry
From
$843
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
14 photos Details
Reviews (27) Make Enquiry
Also consider
$200/nt 9/22-30 - Wailea Ekahi 33A Lux Beach Resort
1 Bedroom, sleeps 5
$265 - $318 / night
WOW !  WHAT A GREAT VIEW ! ---Great Reviews !
2 Bedrooms, sleeps 6
$419 - $541 / night
Wailea Orchid Villa - Panoramic Views!  3 Bd/3 Ba
3 Bedrooms, sleeps 8
$1,055 - $2,433 / night
Wailea Home with Private Pool and Ocean View
3 Bedrooms, sleeps 6
$525 - $737 / night
From
$264
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
34 photos Details
Reviews (25) Make Enquiry
From
$239
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (5) Make Enquiry
From
$207
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Enquiry
From
$254
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
17 photos Details
Reviews (13) Make Enquiry
From
$1,961
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
77 photos Details
Reviews (1) Make Enquiry
Get the List
From
$737
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
59 photos Details
Reviews (14) Make Enquiry
From
$466
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (8) Make Enquiry
From
$292
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 5
8 photos Details
Reviews (17) Make Enquiry
From
$223
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (3) Make Enquiry
From
$201
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
17 photos Details
Reviews (3) Make Enquiry
From
$212
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details
Reviews (3) Make Enquiry
From
$424
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
18 photos Details
Reviews (6) Make Enquiry
From
$297
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (1) Make Enquiry
From
$297
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (1) Make Enquiry
From
$635
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
Reviews (4) Make Enquiry
From
$281
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (22) Make Enquiry
From
$270
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (1) Make Enquiry
From
$949
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
41 photos Details
Reviews (78) Make Enquiry
From
$122
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details
Reviews (9) Make Enquiry
From
$1,929
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (1) Make Enquiry
From
$339
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details
Reviews (20) Make Enquiry
From
$737
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
44 photos Details
Reviews (27) Make Enquiry
From
$169
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
31 photos Details
Reviews (6) Make Enquiry
From
$419
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
23 photos Details
Reviews (16) Make Enquiry
From
$435
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (13) Make Enquiry
From
$211
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Reviews (6) Make Enquiry
From
$186
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
13 photos Details
Reviews (2) Make Enquiry
From
$737
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (18) Make Enquiry
From
$477
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
39 photos Details
Reviews (16) Make Enquiry
From
$281
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details
Reviews (8) Make Enquiry
From
$370
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
35 photos Details
Reviews (14) Make Enquiry
From
$769
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (21) Make Enquiry
From
$360
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
18 photos Details
Reviews (26) Make Enquiry
From
$254
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
21 photos Details
Reviews (2) Make Enquiry
From
$164
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (11) Make Enquiry
From
$419
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
37 photos Details
Reviews (13) Make Enquiry
Go to map view
Book Online(69)
Use filters to find the best results!

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
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
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.