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

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 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 - $225
Per Night

$1365 - $1575
Per Week

Grand Champion #139 - Beautiful Full Renovation !

Wailea
Special Spring 2015 Rates - Please ask ! Beautifully decorated and fully renovated two bedroom cond...
Condo 2 / 2 / 4

*
Online booking available

$285 - $325
Per Night

$1750 - $2065
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

$370 - $370
Per Night

$2590 - $2590
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

$299 - $439
Per Night

$2093 - $4490
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 2015 Rates...
Condo 2 / 2 / 4

*
Online booking available

$285 - $325
Per Night

$1750 - $2065
Per Week

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

$230 - $325
Per Night

$1470 - $2800
Per Week

Wailea Ekolu #314 Spectacular Ocean View 2 Bd 2.5 Bath To...

Wailea
Wailea Ekolu #314 Spectacular Ocean View 2 Bd 2.5 Bath Townhouse Sleeps 4! Unit #314 at Wailea Ekol...
Condo 2 / 2.5 / 4

*
Online booking available

$284 - $384
Per Night

$1988 - $4490
Per Week

Grand Champions #162 - Top Floor with Great Ocean View !

Wailea
Spring 2015 Special Rates!!! As soon as you enter you?ll see the 7th fairway of the golf course wi...
Condo 1 / 2 / 2

*
Online booking available

$185 - $220
Per Night

$1190 - $1435
Per Week

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

Wailea
Grand Champions #49 - Ground Floor, Corner Location with Easy Pool Access ! Special 2015 Spring Rat...
Condo 2 / 2 / 4

*
Online booking available

$250 - $285
Per Night

$1575 - $1820
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 - $296
Per Night

$1183 - $2890
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 - $202
Per Night

$1113 - $2490
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 2015 Special Rates ...
Condo 2 / 2 / 4

*
Online booking available

$250 - $285
Per Night

$1575 - $1820
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 2015 Rates Please Ask! The ...
Condo 2 / 2 / 6

*
Online booking available

$250 - $285
Per Night

$1575 - $1820
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 2015 Rates - Please...
Condo 2 / 2 / 5

*
Online booking available

$250 - $285
Per Night

$1575 - $1820
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 - $329
Per Night

$1393 - $3240
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 ! Relax and spread out i...
Condo 3 / 3.5 / 8

*
Online booking available

$4970 - $5670
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 - $246
Per Night

$1218 - $2990
Per Week

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

Wailea
Wailea Ekolu #1108 2 Bd. 2Ba. Premier Ocean View! Great Rates! Wailea Ekolu is one of most sought a...
Condo 2 / 2 / 6

*
Online booking available

$255 - $325
Per Night

$1785 - $3950
Per Week

Beautifully Renovated and Furnished 2-Bedroom Condo

Wailea
Pool closure notice: The pool will undergo renovations May 4 - June 8, 2015. During this time, there...
Condo 2 / 2 / 6

*
Online booking available

$225 - $320
Per Night

$1470 - $2625
Per Week

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

Wailea
Grand Champions #186 2Br/2Ba Near The Pool, Great Location and many Upgrades. Please ask us about o...
Condo 2 / 2 / 4

*
Online booking available

$250 - $285
Per Night

$1575 - $1820
Per Week

Spacious Renovated 2-bedroom Condo with Central A/C.

Wailea
Pool closure notice: The pool will undergo renovations May 4 - June 8, 2015. During this time, there...
Condo 2 / 2 / 6

*
Online booking available

$250 - $330
Per Night

$1610 - $2625
Per Week

Great Rate for Wailea 2 Bedroom 2 bath Ocean Views!

Wailea
Wailea Ekolu provides a beautiful, relaxing environment and is located on the Wailea Blue golf cours...
Condo 2 / 2 / 6

*
Online booking available

$250 - $250
Per Night

$1750 - $1750
Per Week

Wailea Ekolu #201 Remodeled 2Bd/2Ba Oceanview Condo Sleeps 6

Wailea
Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There...
Condo 2 / 2 / 6

*
Online booking available

$215 - $347
Per Night

$1505 - $3500
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 - $384
Per Night

$1743 - $2990
Per Week

 

More Getaway Locations and Properties