Wailea Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Wailea Beach Villa I-203

Wailea
The “crown jewel” of Wailea- A gated beachfront location, an oceanfront adult pool with a Jacuzzi, ...
Condo 3 / 3 / 6

*
Online booking available

$795 - $1500
Per Night

$5565 - $10500
Per Week

Grand Champions #36

Wailea
This is a great property with a real tropical "Tommy Bahama" feel...Upscale furnishings and attentio...
Condo 2 / 2 / 6

*
Online booking available

$195 - $255
Per Night

$1365 - $1785
Per Week

Wailea Ekahi 1B

Wailea
Beatuiful deluxe 1 bedroom, 2 bath partial ocean view unit in Wailea Ekahi Lower Village - Larger fl...
Condo 1 / 2 / 4

*
Online booking available

$225 - $320
Per Night

$1575 - $2240
Per Week

Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 ...

Wailea
Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 Great Rates The fabulous Keawakapu Beach i...
Condo 2 / 2 / 6

*
Online booking available

$1743 - $3990
Per Week

Grand Champion #139 - Beautiful Full Renovation !

Wailea
Special Spring 2014 Rates - Please ask ! Beautifully decorated and fully renovated two bedroom cond...
Condo 2 / 2 / 4

*
Online booking available

$275 - $315
Per Night

$1680 - $1995
Per Week

Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd ...

Wailea
Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd 2Bath Great Rates! The fabulous Keawakapu ...
Condo 2 / 2 / 4

*
Online booking available

$284 - $324
Per Night

$1988 - $3990
Per Week

Grand Champions #163 2Br/2Ba Convenient 1st Floor Locatio...

Wailea
Grand Champions #163 2Br/2Ba Convenient 1st Floor Location. 2011 Remodel! Special Spring 2014 Rates...
Condo 2 / 2 / 4

*
Online booking available

$275 - $315
Per Night

$1680 - $1995
Per Week

Palms 1507- 2B/2B Elegant Remodel; Views of ocean and mou...

Wailea
Palms 1507- 2B/2B Elegant Remodel; Views of ocean and mountains. Beautiful place! You really though...
Condo 2 / 2 / 4

*
Online booking available

$249 - $349
Per Night

$1743 - $3990
Per Week

Grand Champions #35 Ocean View 2R/2Br Upper Floor - Great...

Wailea
Grand Champions #35 Ocean View 2R/2Br Upper Floor - Great Rates! Special Spring 2014 Rates - Please...
Condo 2 / 2 / 5

*
Online booking available

$240 - $275
Per Night

$1505 - $1750
Per Week

Ho'olei #t6 - Biggest Floor Plan. Close to Wailea Beach -...

Wailea
Ho'olei #t6 - Biggest Floor Plan. Close to Wailea Beach - Great 2013 Rates ! Special Fall 2013 Rate...
Condo 3 / 4 / 8

*
Online booking available

$4795 - $5495
Per Week

Palms at Wailea #1204 Ocean View 2Bd 2 Ba Sleeps 6 Great ...

Wailea
Palms at Wailea #1204 Ocean View 2Bd 2 Ba Sleeps 6 Great Rates! The fabulous Keawakapu Beach is jus...
Condo 2 / 2 / 4

*
Online booking available

$199 - $299
Per Night

$1393 - $2990
Per Week

Grand Chamapions #48 Great Ocean Views! 2Bd 2 Ba Great Ra...

Wailea
Grand Chamapions #48 Great Ocean Views! 2Bd 2 Ba Great Rates!! The nearby Ulua and Mokapu Beaches a...
Condo 2 / 2 / 6

*
Online booking available

$174 - $224
Per Night

$1218 - $2990
Per Week

Wailea Ekahi 46F

Wailea
Wailea Ekahi - Nicely appointed 2 bedroom, 2 bath condo with garden and partial oceanview in the Upp...
Condo 2 / 2 / 6

*
Online booking available

$252 - $370
Per Night

$1764 - $2590
Per Week

Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. ...

Wailea
Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 6. The nearby Ulua and Mokapu...
Condo 2 / 2 / 6

*
Online booking available

$199 - $224
Per Night

$1393 - $2990
Per Week

Palms at Wailea 702 Upstairs Garden View 1Bd 2Ba Sleeps 4...

Wailea
Palms at Wailea 702 Upstairs Garden View 1Bd 2Ba Sleeps 4 Great Rates! The fabulous Keawakapu Beach...
Condo 1 / 2 / 4

*
Online booking available

$159 - $224
Per Night

$1113 - $2790
Per Week

Wailea Elua #2105 - Panoramic Ocean View 2 Bd 2 Ba - Grea...

Wailea
Wailea Elua #2105 - Panoramic Ocean View 2 Bd 2 Ba - Great Rates! The Wailea Elua is the premier oc...
Condo 2 / 2 / 6

*
Online booking available

$349 - $349
Per Night

$2443 - $5250
Per Week

Wailea Ekolu #103 2Bd 2Ba Ground Floor Sleeps 6 Great Rates!

Wailea
Unit #103 is located in the closest building to the beach in the entire complex. This condo has a fu...
Condo 2 / 2 / 6

*
Online booking available

$189 - $224
Per Night

$1323 - $2990
Per Week

Wailea Ekahi 1A

Wailea
Enjoy your vacation filled with family fun or calm serenity in this inviting 1 bedroom, 2 bath condo...
Condo 1 / 2 / 4

*
Online booking available

$194 - $285
Per Night

$1355 - $1995
Per Week

Grand Champions #186 2Br/2Ba Near The Pool, Great Location

Wailea
Please ask us about our Spring 2014 Specials. Grand Champions 186 is located on the second floor an...
Condo 2 / 2 / 4

*
Online booking available

$240 - $275
Per Night

$1505 - $1750
Per Week

Wailea Ekahi 39D

Wailea
Wailea Ekahi - newly renovated/updated 1 bedroom, 1 bath condo. Partial Ocean View unit located on ...
Condo 1 / 1 / 2

*
Online booking available

$225 - $320
Per Night

$1575 - $2240
Per Week

Palms at Wailea #202 Gorgeous 1 Bd 2 Bath Beautifully dec...

Wailea
Palms at Wailea #202 Gorgeous 1 Bd 2 Bath Beautifully decorated. The fabulous Keawakapu Beach is ju...
Condo 1 / 2 / 4

*
Online booking available

$179 - $249
Per Night

$1253 - $2790
Per Week

Ho'olei #55-2 Luxurious New Wailea Rental Home

Wailea
April 2014 Specials - Please ASK ! Relax in this spectacular three bedroom deluxe accommodation. B...
Condo 3 / 4 / 8

*
Online booking available

$4795 - $5495
Per Week

Wailea Ekolu #102 2 Bd 2 Bath Sleeps 6 Great Rates!!

Wailea
Unit #102 is located in the closest building to the beach in the entire complex. This condo has a fu...
Condo 2 / 2 / 6

*
Online booking available

$189 - $289
Per Night

$1323 - $2990
Per Week

Grand Champions #49 - Ground Floor, Corner Location with ...

Wailea
Beautifully Remodeled Ground Floor End Unit at Grand Champions with Tile Floor, Newly Remodeled Kitc...
Condo 2 / 2 / 4

*
Online booking available

$240 - $275
Per Night

$1505 - $1750
Per Week

Beautifully Renovated and Funished!!!!!

Wailea
2 bedroom 2 bath condo is an amazingly comfortable place to stay while enjoying your trip to Maui. T...
Condo 2 / 2 / 6

*
Online booking available

$225 - $315
Per Night

$1470 - $2625
Per Week

 

More Getaway Locations and Properties