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 Ekolu 1205, 2 Bedrooms, Wifi, Ocean View, Pool Acc...

Wailea
Begin your day with an alfresco breakfast on your covered lanai while gazing out at palm trees and t...
Condo 2 / 2 / 4

*
Online booking available

$284 - $846
Per Night

$1988 - $5925
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

$235 - $493
Per Night

$1645 - $3450
Per Week

Palms at Wailea 1606 - 2 Bedrooms, Spacious Condo, Pool, ...

Wailea
The lush scenery cannot be beat at Palms at Wailea 1606! This beautiful condo features two spacious...
Condo 2 / 2 / 6

*
Online booking available

$204 - $681
Per Night

$1428 - $4765
Per Week

Palms at Wailea Unit #2305 Quiet and Very Private!

Wailea
We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the num...
Condo 1 / 2 / 2

*
Online booking available

$179 - $427
Per Night

$1253 - $2990
Per Week

Grand Champions 186 - 2 Bedrooms, 2nd Floor, Overlooking ...

Wailea
This stunningly renovated condo has everything you need for an incredible Hawaiian vacation! With go...
Condo 2 / 2 / 4

*
Online booking available

$204 - $681
Per Night

$1428 - $4765
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

$200 - $484
Per Night

$1400 - $3390
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

Wailea Ekolu #406 2 Bd 2Ba Panoramic Ocean View, Full A/C...

Wailea
Wailea Ekolu #406 2 Bd 2Ba Panoramic Ocean View, Full A/C, Sleeps 4 If you love sitting on a large,...
Condo 2 / 2 / 4

*
Online booking available

$255 - $641
Per Night

$1785 - $4490
Per Week

2B/2B Beautifully Furnished, Great Rates, Sleeps 6

Wailea
Palms at Wailea #606 The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at...
Condo 2 / 2 / 6

*
Online booking available

$210 - $550
Per Night

$1470 - $3850
Per Week

Palms at Wailea #604 2/2 Great for 2 Couples Super 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

$189 - $463
Per Night

$1323 - $3240
Per Week

Wailea Ekolu 1106 - 2 Bedrooms, Modern Updates, Ocean Vie...

Wailea
With amazing ocean views of Kahoolawe, Molokini, and Lana’i, Wailea Ekolu 1106 has a lanai that is j...
Condo 2 / 2 / 4

*
Online booking available

$265 - $772
Per Night

$1855 - $5405
Per Week

Summer Special! Wailea Ekahi 48C ~ 1 BR 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

$225 - $280
Per Night

$1575 - $1960
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

$250 - $570
Per Night

$1750 - $3990
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 - $464
Per Night

$1393 - $3250
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

$200 - $463
Per Night

$1400 - $3240
Per Week

Grand Champions 144 - 3 Bedrooms, Ocean and Golf Views, 2...

Wailea
Whether you are looking for a relaxing getaway or seeking adventure of all kinds, Maui is the perfec...
Condo 3 / 2 / 6

*
Online booking available

$327 - $955
Per Night

$2289 - $6687
Per Week

Palms at Wailea #1209 1 BR 2 Bath Sleeps 4. Great Rates!

Wailea
The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach i...
Condo 1 / 2 / 4

*
Online booking available

$210 - $393
Per Night

$1470 - $2750
Per Week

Grand Champions 181 - 1 Bedroom Condo, Beautifully Renova...

Wailea
Located on the edge of the Wailea Blue Golf Course, Grand Champions 181 is an ideal getaway for the ...
Condo 1 / 2 / 4

*
Online booking available

$140 - $410
Per Night

$980 - $2872
Per Week

Grand Champions 35, 2 Bedrooms, 3rd Floor, Ocean View, Po...

Wailea
Palm trees swaying in the breeze, tropical air filling your senses, and a great ocean view are waiti...
Condo 2 / 2 / 5

*
Online booking available

$224 - $681
Per Night

$1571 - $4765
Per Week

Grand Champions 108, 1 Bedroom, Cozy Lanai, Pool Access, ...

Wailea
Grand Champions 108 is made for romance. The balcony of the 1-bedroom condo looks out over the compl...
Condo 1 / 2 / 2

*
Online booking available

$144 - $846
Per Night

$1008 - $5925
Per Week

 

More Getaway Locations and Properties