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

One-of-a-kind Maui Getaway!

Wailea
This One-of-a-Kind Maui Getaway is just the vacation destination you have been dreaming of! Owner...
Home 4 / 3.5 / 10

$1450 - $1600
Per Night

Grand Champion #139 - Beautiful Full Renovation 2015 !

Wailea
Spring Saver Rates 2017 - Book Early ! Beautifully decorated and fully renovated two bedroom condom...
Condo 2 / 2 / 4

*
Online booking available

$295 - $340
Per Night

$1820 - $2415
Per Week

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

Wailea
Spring Saver Rates 2017! Book Early ! Grand Champions 163 is a delightful ground floor two bedroom t...
Condo 2 / 2 / 4

*
Online booking available

$260 - $285
Per Night

$1645 - $2170
Per Week

Wailea Ekahi 46F- Spacious 2 bedroom 2 Bath Condo in Wailea!

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

$280 - $380
Per Night

$1962 - $2660
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

$329 - $684
Per Night

$2303 - $4790
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 - $641
Per Night

$2093 - $4490
Per Week

Grand Champions #121

Wailea
Spring Saver Rates 2017 ! Grand Champions 121 offers a flat screen TV, DVD player, CD player and hig...
Condo 1 / 2 / 4

*
Online booking available

$190 - $230
Per Night

$1190 - $1715
Per Week

Grand Champions #132 - Top Floor with Tennis Center and D...

Wailea
Grand Champions #132 - Top Floor with Tennis Center and Distant Ocean Views. Spring Saver Rate 2017...
Condo 1 / 2 / 2

*
Online booking available

$230 - $265
Per Night

$1505 - $1995
Per Week

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

Wailea
Spring Saver Rates 2017 ! As soon as you enter you?ll see the 7th fairway of the golf course with ...
Condo 1 / 2 / 2

*
Online booking available

$190 - $230
Per Night

$1225 - $1890
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 - $463
Per Night

$1393 - $3240
Per Week

Palms at Wailea 1902 Garden View 2Bd 2Ba Sleeps 6

Wailea
Enjoy your stay in paradise at The Palms at Wailea, a gorgeous property with lush, tropical landscap...
Condo 2 / 2 / 6

*
Online booking available

$224 - $463
Per Night

$1568 - $3240
Per Week

Wailea Ekolu #804 Best Panoramic Ocean View 1Bd 2Ba Priva...

Wailea
Wailea Ekolu #804 Best Panoramic Ocean View 1Bd 2Ba Private location! Wailea Ekolu is one of most s...
Condo 1 / 2 / 4

*
Online booking available

$225 - $499
Per Night

$1575 - $3490
Per Week

Grand Champions #143 is a 3 BR 2 bath renovated Summer Sp...

Wailea
Grand Champions #143 is a 3 BR 2 bath renovated Summer Special $299 Unit 143 at the Wailea Grand Ch...
Condo 3 / 2 / 8

*
Online booking available

$325 - $750
Per Night

$2275 - $5250
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 ! Special Deals Spring Saver Rates 201...
Condo 3 / 3.5 / 8

*
Online booking available

$810 - $965
Per Night

$5670 - $11165
Per Week

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

Wailea
Grand Champions #165, 2Br/2Ba On The Golf Course - Great Rates! Spring Saver Rates 2017!! Book Earl...
Condo 2 / 2 / 4

*
Online booking available

$260 - $305
Per Night

$1645 - $2170
Per Week

Wailea Ekolu #105 Partial Ocean view, Sleeps 4

Wailea
Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There...
Condo 2 / 2 / 4

*
Online booking available

$239 - $607
Per Night

$1673 - $4250
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 - $564
Per Night

$1505 - $3950
Per Week

Grand Champions 181 - Spacious Remodeled 1-Bedroom

Wailea
Unit 181 is located in the heart of the beautiful and serene Grand Champions Villas. On the edge of ...
Condo 1 / 2 / 4

*
Online booking available

$130 - $350
Per Night

$910 - $2449
Per Week

Wailea Elua #2110 - Gorgeous Ocean View 2B/2B

Wailea
The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has ...
Condo 2 / 2 / 5

*
Online booking available

$345 - $750
Per Night

$2415 - $5250
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 - $463
Per Night

$1575 - $3240
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 - $427
Per Night

$1218 - $2990
Per Week

Up to 30% OFF through April! - Grand Champions #090

Wailea
Beautifully Remodeled and furnished two bedroom Condo overlooking the Golf Course. The kitchen ad ba...
Condo 2 / 2 / 6

*
Online booking available

$425 - $515
Per Night

$2975 - $3605
Per Week

Grand Champions 75 - Ocean and Fairway Views

Wailea
Relax on your lanai, enjoying the radiant blue waters to your west, and the stunning sights of Halea...
Condo 2 / 2 / 4

*
Online booking available

$167 - $474
Per Night

$1167 - $3320
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 - $356
Per Night

$1113 - $2490
Per Week

Palms at Wailea 702 Upstairs Garden View 1B/2B Sleeps 4. ...

Wailea
Palms at Wailea 702 Upstairs Garden View 1B/2B Sleeps 4. Summer Special $169 The fabulous Keawakapu...
Condo 1 / 2 / 4

*
Online booking available

$169 - $427
Per Night

$1183 - $2990
Per Week

 

More Getaway Locations and Properties