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

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 202 Rentals in Wailea
loading...
Sort by
From
$793
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
60 photos Details
Reviews (14) Make Enquiry
From
$1,313
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
83 photos Details
Reviews (1) Make Enquiry
From
$274
Per Night
Studio, 1 Bathroom, Sleeps 2
18 photos Details
Reviews (5) Make Enquiry
Also consider
Ocean View, Remodeled, "SPECIAL" Open nights Oct $175.00 + cleaning fee
2 Bedrooms, sleeps 6
$285 - $371 / night
Wailea Ekahi Village-Luxury 1BR condo for couples
1 Bedroom, sleeps 2
$217 - $280 / night
Beautiful Modern Wailea! Remodeled & Affordable
1 Bedroom, sleeps 4
$137 - $205 / night
Modern Stylish Condo, Designer Touches Throughout!
2 Bedrooms, sleeps 6
$211 - $314 / night
From
$240
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (5) Make Enquiry
From
$451
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
37 photos Details
Reviews (13) Make Enquiry
From
$204
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (13) Make Enquiry
From
$223
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Enquiry
From
$6,033
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
27 photos Details
Reviews (6) Make Enquiry
Get the List
From
$406
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (1) Make Enquiry
From
$337
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
Reviews (2) Make Enquiry
From
$228
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (5) Make Enquiry
From
$223
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details
Reviews (1) Make Enquiry
From
$268
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (21) Make Enquiry
From
$2,078
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (1) Make Enquiry
From
$468
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (13) Make Enquiry
From
$451
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
23 photos Details
Reviews (17) Make Enquiry
From
$1,136
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Reviews (5) Make Enquiry
From
$285
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 5
8 photos Details
Reviews (17) Make Enquiry
From
$684
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
Reviews (4) Make Enquiry
From
$337
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (2) Make Enquiry
From
$217
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
17 photos Details
Reviews (3) Make Enquiry
From
$211
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (4) Make Enquiry
From
$793
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (18) Make Enquiry
From
$148
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
25 photos Details
Reviews (19) Make Enquiry
From
$457
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
18 photos Details
Reviews (6) Make Enquiry
From
$285
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 5
21 photos Details
Reviews (14) Make Enquiry
From
$331
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (11) Make Enquiry
From
$228
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details
Reviews (3) Make Enquiry
From
$303
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details
Reviews (9) Make Enquiry
From
$223
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details
Reviews (3) Make Enquiry
From
$468
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (24) Make Enquiry
From
$227
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
21 photos Details
Reviews (4) Make Enquiry
From
$342
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (23) Make Enquiry
From
$291
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (1) Make Enquiry
From
$131
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details
Reviews (9) Make Enquiry
From
$303
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (22) Make Enquiry
From
$227
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
Reviews (18) Make Enquiry
From
$227
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (16) Make Enquiry
From
$1,136
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
76 photos Details
Reviews (1) Make Enquiry
From
$628
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (33) Make Enquiry
Go to map view
Book Online(76)
Use filters to find the best results!

Suitability

  • Wheelchair access (15)
  • Elder access (60)
  • Suitable for children (55)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Internet (182)
  • Grill (161)
  • All pools (160)
  • Air Conditioning (159)
  • Public pool (156)
  • 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.