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.

Vacation rentals in Wailea, Maui

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
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 233 Rentals in Wailea
loading...
Sort by
From
$214
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details
Reviews (1) Make Enquiry
From
$391
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (1) Make Enquiry
From
$764
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
44 photos Details
Reviews (27) Make Enquiry
Also consider
Luxury Wailea Beach Villa great price! From $725!
2 Bedrooms, sleeps 6
$796 - $1,373 / night
Totally renovated, closest to the beach!
1 Bedroom, sleeps 5
$275 - $385 / night
Modern Stylish Condo, Designer Touches Throughout!
2 Bedrooms, sleeps 6
$203 - $302 / night
Charming Private Studio!  Affordable Wailea
1 Bedroom, sleeps 2
$126 - $154 / night
From
$302
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
21 photos Details
Reviews (4) Make Enquiry
From
$209
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
30 photos Details
Reviews (1) Make Enquiry
From
$405
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Enquiry
From
$231
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Make Enquiry
From
$428
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
14 photos Details
Make Enquiry
Get the List
From
$247
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
23 photos Details
Make Enquiry
From
$209
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
17 photos Details
Make Enquiry
From
$323
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
17 photos Details
Make Enquiry
From
$214
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
13 photos Details
Make Enquiry
From
$214
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details
Make Enquiry
From
$153
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details
Make Enquiry
From
$324
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
7 photos Details
Make Enquiry
From
$209
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
11 photos Details
Make Enquiry
From
$5,806
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
27 photos Details
Reviews (6) Make Enquiry
From
$1,533
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
74 photos Details
Reviews (8) Make Enquiry
From
$390
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (1) Make Enquiry
From
$483
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (8) Make Enquiry
From
$197
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (5) Make Enquiry
From
$214
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Enquiry
From
$274
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (34) Make Enquiry
From
$312
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 4
42 photos Details
Reviews (12) Make Enquiry
From
$324
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (2) Make Enquiry
From
$604
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (33) Make Enquiry
From
$231
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (5) Make Enquiry
From
$439
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
18 photos Details
Reviews (6) Make Enquiry
From
$1,999
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (1) Make Enquiry
From
$1,093
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Reviews (5) Make Enquiry
From
$291
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details
Reviews (9) Make Enquiry
From
$434
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
30 photos Details
Reviews (3) Make Enquiry
From
$769
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (1) Make Enquiry
From
$1,263
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
82 photos Details
Reviews (1) Make Enquiry
From
$203
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (4) Make Enquiry
From
$764
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (18) Make Enquiry
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
Reviews (10) Make Enquiry
From
$292
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details
Reviews (1) Make Enquiry
From
$1,752
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
73 photos Details
Reviews (10) Make Enquiry
From
$379
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details
Reviews (8) Make Enquiry
Go to map view
Book Online(78)
Use filters to find the best results!

Suitability

  • Wheelchair access (15)
  • Elder access (60)
  • Suitable for children (58)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Grill (190)
  • Internet (185)
  • All pools (165)
  • Air Conditioning (160)
  • Public pool (158)
  • 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 Vacation Rentals

Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

A Wailea Vacation

No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

Family-Friendly Wailea

From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.