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

Stunning 3-BR Condo on a World-Class Golf Course Resort.

Wailea
Grand Champions 123 is located in a quiet setting in Wailea. Large green belts, manicured grounds an...
Condo 3 / 2 / 6

*
Online booking available

$200 - $335
Per Night

$1330 - $2800
Per Week

Ho'olei #39-3 'Ocean's Invitation' Premier Location and V...

Wailea
Ho'olei #39-3 'Ocean's Invitation' Premier Location and View ! Enjoy more than 2700 feet of comfort...
Condo 3 / 3.5 / 8

*
Online booking available

$5670 - $6545
Per Week

Palms at Wailea 603 2bd 2ba Sleeps 6 Great Rates!!

Wailea
The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach i...
Condo 2 / 2 / 6

*
Online booking available

$199 - $299
Per Night

$1393 - $3240
Per Week

Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Go...

Wailea
Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4. The nearby Ulua and M...
Condo 1 / 2 / 4

*
Online booking available

$159 - $184
Per Night

$1113 - $2490
Per Week

Beautiful 2-Bedroom Condo with a Partial Ocean View

Wailea
This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious...
Condo 2 / 2 / 6

*
Online booking available

$180 - $320
Per Night

$1190 - $2450
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

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

Wailea
Grand Champions #35 Ocean View 2R/2Br Upper Floor - Great Rates! Special Spring 2016 Rates - Please...
Condo 2 / 2 / 5

*
Online booking available

$250 - $295
Per Night

$1575 - $1890
Per Week

Grand Champions #165, 2Br/2Ba On The Golf Course - Great ...

Wailea
Grand Champions #165, 2Br/2Ba On The Golf Course - Great Rates! Special 2016 Rates Please Ask! The ...
Condo 2 / 2 / 4

*
Online booking available

$250 - $295
Per Night

$1575 - $1890
Per Week

Wailea Elua #2110 - Gorgeous Ocean View 2B/2B - Winter Sp...

Wailea
Wailea Elua #2110 - Gorgeous Ocean View 2B/2B - Winter Special $425 / Night The Wailea Elua is the ...
Condo 2 / 2 / 5

*
Online booking available

$395 - $425
Per Night

$2765 - $5250
Per Week

Wailea Ekolu #102 2 Bd 2 Bath, Ocean View, A/C, Sleeps 6 ...

Wailea
Wailea Ekolu #102 2 Bd 2 Bath, Ocean View, A/C, Sleeps 6 Great Rates!! Unit #102 is located in the ...
Condo 2 / 2 / 6

*
Online booking available

$189 - $289
Per Night

$1323 - $2990
Per Week

Grand Champions #51 is a 2Bd 2Ba is a large condo that sl...

Wailea
Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates! The nearby Ulua and M...
Condo 2 / 2 / 6

*
Online booking available

$174 - $224
Per Night

$1218 - $2990
Per Week

Grand Champions #45 is a 2bd 2ba Ocean view condo that Sl...

Wailea
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates! The nearby Ulua and Mo...
Condo 2 / 2 / 6

*
Online booking available

$199 - $224
Per Night

$1393 - $2990
Per Week

Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!

Wailea
Wailea Ekahi Village - 1 bedroom, 2 bath condo with a calming garden view located in the Upper Villa...
Condo 1 / 2 / 4

*
Online booking available

$200 - $250
Per Night

$1400 - $1750
Per Week

Wailea Ekolu #1108 2 Bd. 2Ba. Premier Ocean View!

Wailea
Wailea Ekolu is one of most sought after properties in Wailea as it is nestled on the Wailea Golf Co...
Condo 2 / 2 / 6

*
Online booking available

$255 - $295
Per Night

$1505 - $3950
Per Week

Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! ...

Wailea
Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! 2/2 Great Rates! The fabulous Keawakapu Be...
Condo 2 / 2 / 4

*
Online booking available

$249 - $349
Per Night

$1743 - $3990
Per Week

Palms at Wailea #1102 Probably the best ocean view at the...

Wailea
Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea! The fabulous Keawakapu B...
Condo 2 / 2 / 6

*
Online booking available

$295 - $395
Per Night

$2065 - $4950
Per Week

Palms at Wailea #1501 Ocean View Inner Court Ground Floor...

Wailea
Palms at Wailea #1501 Ocean View Inner Court Ground Floor 1Bd 1Ba Sleeps 4 The fabulous Keawakapu B...
Condo 1 / 2 / 4

*
Online booking available

$225 - $299
Per Night

$1575 - $3240
Per Week

Palms at Wailea 2303 Ground Floor 2bd 2ba Sleeps 6 Great ...

Wailea
Palms at Wailea 2303 Ground Floor 2bd 2ba Sleeps 6 Great Rates! We are pleased that our properties ...
Condo 2 / 2 / 6

*
Online booking available

$199 - $299
Per Night

$1393 - $3240
Per Week

Grand Champions #48 is a 2bd 2ba Ocean View condo that Sl...

Wailea
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates! The nearby Ulua and Mo...
Condo 2 / 2 / 6

*
Online booking available

$199 - $224
Per Night

$1393 - $2990
Per Week

Ho'olei #55-2 Luxurious and Spacious Wailea Rental Home

Wailea
Special Winter and Spring 2016 Pricing - Please Ask ! Relax in this spectacular three bedroom delu...
Condo 3 / 3.5 / 8

*
Online booking available

$4970 - $5845
Per Week

Palms at Wailea 609 Ground Level Garden View - 1Bd 2Ba Sl...

Wailea
Palms at Wailea 609 Ground Level Garden View - 1Bd 2Ba Sleeps 4: Great Rates! The fabulous Keawakap...
Condo 1 / 2 / 4

*
Online booking available

$169 - $269
Per Night

$1183 - $2890
Per Week

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

Wailea
Grand Champions #49 - Ground Floor, Corner Location with Easy Pool Access ! Special 2016 Spring Rat...
Condo 2 / 2 / 4

*
Online booking available

$250 - $295
Per Night

$1575 - $1890
Per Week

Beautifully Renovated 1-BR Condo, Nearby World-Class Golf...

Wailea
Beautifully Renovated 1-BR Condo, Nearby World-Class Golf and Shopping. Unit 181 is located in the ...
Condo 1 / 2 / 4

*
Online booking available

$130 - $220
Per Night

$805 - $1645
Per Week

Grand Champions #102 2Br/2Ba Golf Course and Mountain Vie...

Wailea
Grand Champions #102 2Br/2Ba Golf Course and Mountain Views - Best Rates Spring 2016 Special Rates ...
Condo 2 / 2 / 4

*
Online booking available

$250 - $295
Per Night

$1575 - $1890
Per Week

Palms at Wailea #1204 Ocean View, Sleeps 4.

Wailea
The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. Keawakapu Be...
Condo 2 / 2 / 4

*
Online booking available

$225 - $299
Per Night

$1575 - $3240
Per Week

 

More Getaway Locations and Properties