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

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

Wailea
Grand Champions #163 2Br/2Ba Convenient 1st Floor Location. 2011 Remodel! Special Spring & Fall 201...
Condo 2 / 2 / 4

*
Online booking available

$275 - $325
Per Night

$1680 - $2275
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 - $399
Per Night

$2093 - $3990
Per Week

Wailea Ekahi 1B

Wailea
Beautiful 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

Grand Champion #139 - Beautiful Full Renovation !

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

*
Online booking available

$275 - $325
Per Night

$1680 - $2275
Per Week

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

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

Wailea Ekolu 805 Deluxe 2 Bd. 2 Bath, Ocean View Townhouse!

Wailea
Unit #805 has a fully equipped kitchen, AC in the living room, guest bedroom, and master bedroom. Th...
Condo 2 / 2 / 4

*
Online booking available

$199 - $289
Per Night

$1393 - $3490
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

Palms at Wailea #1204 Ocean View 2Bd 2 Ba Sleeps 4 Great ...

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

*
Online booking available

$199 - $299
Per Night

$1393 - $2990
Per Week

Palms at Wailea Unit #2305 Quiet, Clean and Very Private!...

Wailea
Palms at Wailea Unit #2305 Quiet, Clean and Very Private! Great Rates!! We are pleased that our pro...
Condo 1 / 2 / 2

*
Online booking available

$159 - $249
Per Night

$1113 - $2790
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

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

Grand Champions #121

Wailea
Summer & Fall 2014 Specials - Please Ask. Grand Champions 121 offers a flat screen TV, DVD player, C...
Condo 1 / 2 / 4

*
Online booking available

$180 - $220
Per Night

$1155 - $1540
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 ! Spring & Fall 2014 - Super Special R...
Condo 3 / 4 / 8

*
Online booking available

$5495 - $11165
Per Week

Palms at Wailea #1406 Panoramic Ocean Views 2Bd 2Bath Gre...

Wailea
Palms at Wailea #1406 Panoramic Ocean Views 2Bd 2Bath Great Rates! The fabulous Keawakapu Beach is ...
Condo 2 / 2 / 6

*
Online booking available

$199 - $299
Per Night

$1393 - $2990
Per Week

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

Wailea
Grand Champions #49 - Ground Floor, Corner Location with Easy Pool Access ! Special 2014 Spring & ...
Condo 2 / 2 / 4

*
Online booking available

$240 - $285
Per Night

$1505 - $1995
Per Week

Beautifully Renovated and Funished

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

*
Online booking available

$225 - $315
Per Night

$1470 - $2625
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 #1005 Panoramic Ocean Views 1Bd 2Ba Sleep...

Wailea
Palms at Wailea #1005 Panoramic Ocean Views 1Bd 2Ba Sleeps 6 Great Rates! The fabulous Keawakapu Be...
Condo 1 / 2 / 4

*
Online booking available

$179 - $249
Per Night

$1253 - $2790
Per Week

Wailea Elua #2110 - Gorgeous Ocean View 2 Bd 2 Ba - Great...

Wailea
Wailea Elua #2110 - Gorgeous Ocean View 2 Bd 2 Ba - Great Rates! The Wailea Elua is the premier oce...
Condo 2 / 2 / 5

*
Online booking available

$395 - $495
Per Night

$2765 - $5250
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 - $189
Per Night

$1113 - $2490
Per Week

Wailea Ekolu #210 2 Story Townhouse 2 BR 3 Bath Ocean Vie...

Wailea
Wailea Ekolu #210 2 Story Townhouse 2 BR 3 Bath Ocean View Sleeps 6 Wailea Ekolu is one of most sou...
Condo 2 / 3 / 6

*
Online booking available

$199 - $289
Per Night

$1393 - $3490
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 #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

$159 - $224
Per Night

$1113 - $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 - $295
Per Night

$1785 - $3150
Per Week

 

More Getaway Locations and Properties