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.

Hoolei Vacation Rentals

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 $10,000 Peace of Mind Guarantee
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
Advanced
Tip: Refine your search by price, amenities, & more (see left column).
Searching … 0% complete
17 Hoolei Vacation Rentals
loading...
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Perfect Escape! Ho'Olei Dream -Super Close to Pool to your Saves list
from
$800
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Ho'olei with Grand Wailea Resort Access & Views to your Saves list
from
$1,288
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Hoku at Ho'olei - Grand Wailea Resort Privileges to your Saves list
from
$1,095
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
from
$755
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
from
$655
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
Save
You added Ho'olei-Ocean View Wailea Beach Maui,Sleeps 10 to your Saves list
from
$695
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
from
$755
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Wailea Luxury Villas, 6-10 Occupancy, Beach Pool to your Saves list
from
$655
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Ho’olei Resort - The Spirit of Aloha (S2), Hawaii to your Saves list
from
$850
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
from
$655
Per Night
Get the List
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Three Bedroom Home in Wailea - Ho'olei S (12) 2 to your Saves list
from
$795
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
Save
You added Ho'olei Beautiful Home, Close to Pool and Beach to your Saves list
from
$750
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Ho’olei Resort - Moe'uhane (S6), Hawaii to your Saves list
from
$850
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Ho’olei Resort - Palekaiko (S1), Hawaii to your Saves list
from
$850
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
from
$800
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Free gift worth $249
Save
You added Ho’olei Resort - Lani Kauwahi (T2), Hawaii to your Saves list
from
$850
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
from
$750
Per Night
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.

View larger map
Book Online(0)
Popular cities
Own a rental property?
Want more exposure for your rental? Get listed in TripAdvisor Vacation Rentals (in partnership with FlipKey).
Free Newsletter

Sign up to hear about gorgeous vacation rentals, the latest deals, exciting destinations, and more.

Get the List

More Romance destinations:

More Beach destinations:

More Family destinations: