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

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
My dates are flexible
Advanced
All 247 Rentals in Wailea
loading...
Sort by
From
$440
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
21 photos Details
Reviews (8) Make Inquiry
From
$284
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 4
42 photos Details
Reviews (10) Make Inquiry
From
$240
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (3) Make Inquiry
Also consider
Wailea Ekahi, Privacy and Luxury - $119-239/nt
1 Bedroom, sleeps 4
$119 - $239 / night
Stylish Renovated Modern with Large Private Lanai!
2 Bedrooms, sleeps 6
$185 - $250 / night
Hale Kamaole 265 Oceanview Updated 2BR plus Loft
3 Bedrooms, sleeps 6
$215 - $260 / night
Ekahi 44C Private Remodeled Oceanview Townhouse
1 Bedroom, sleeps 4
$265 - $320 / night
From
$599
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
15 photos Details
Reviews (8) Make Inquiry
From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (17) Make Inquiry
From
$555
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
Reviews (7) Make Inquiry
From
$252
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (1) Make Inquiry
From
$195
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Inquiry
Get the List
From
$210
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (3) Make Inquiry
From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (5) Make Inquiry
From
$249
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (34) Make Inquiry
From
$795
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
59 photos Details
Reviews (14) Make Inquiry
From
$255
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (1) Make Inquiry
From
$225
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
13 photos Details
Reviews (2) Make Inquiry
From
$410
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (12) Make Inquiry
From
$1,195
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
88 photos Details
Reviews (2) Make Inquiry
From
$599
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
Reviews (4) Make Inquiry
From
$695
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (18) Make Inquiry
From
$455
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (33) Make Inquiry
From
$1,820
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (1) Make Inquiry
From
$250
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
48 photos Details
Reviews (15) Make Inquiry
From
$235
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (20) Make Inquiry
From
$395
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
23 photos Details
Reviews (15) Make Inquiry
From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (15) Make Inquiry
From
$725
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (21) Make Inquiry
From
$185
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details
Reviews (3) Make Inquiry
From
$235
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (37) Make Inquiry
From
$165
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (4) Make Inquiry
From
$395
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (33) Make Inquiry
From
$625
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (9) Make Inquiry
From
$450
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
39 photos Details
Reviews (14) Make Inquiry
From
$240
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
21 photos Details
Reviews (2) Make Inquiry
From
$400
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
18 photos Details
Reviews (6) Make Inquiry
From
$295
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
16 photos Details
Reviews (1) Make Inquiry
From
$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (22) Make Inquiry
From
$185
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
Reviews (4) Make Inquiry
From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details
Reviews (9) Make Inquiry
From
$290
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
18 photos Details
Reviews (11) Make Inquiry
From
$320
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details
Reviews (19) Make Inquiry
From
$280
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (1) Make Inquiry
Go to map view
Book Online(70)

Suitability

  • Wheelchair access (16)
  • Elder access (65)
  • Suitable for children (55)
  • Pet friendly (2)
  • Smoking allowed (0)

Amenities

  • Washer/Dryer (227)
  • Grill (216)
  • Air Conditioning (213)
  • All pools (213)
  • Internet (184)
  • 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

More Romance destinations:

More Beach destinations:

More Family destinations:

Filter search results by:
Book Online(70)

Suitability

  • Wheelchair access (16)
  • Elder access (65)
  • Suitable for children (55)
  • Pet friendly (2)
  • Smoking allowed (0)

Amenities

  • Washer/Dryer (227)
  • Grill (216)
  • Air Conditioning (213)
  • All pools (213)
  • Internet (184)
  • View all amenities
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.