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 #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

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

$266 - $370
Per Night

$1862 - $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 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

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 - $285
Per Night

$1750 - $1750
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

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 - $250
Per Night

$1575 - $1575
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

Wailea Elua #2105 Oceanview 2Bd/2Ba Sleeps 6 Great Rates!

Wailea
The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has ...
Condo 2 / 2 / 6

*
Online booking available

$349 - $359
Per Night

$2443 - $5250
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 - $435
Per Night

$2065 - $4950
Per Week

Palms at Wailea #1606 Spacious 2Br/2Ba - Great Rates - Fr...

Wailea
Palms at Wailea #1606 Spacious 2Br/2Ba - Great Rates - Free Wifi ! Special Spring 2015 Rates. Plea...
Condo 2 / 2 / 6

*
Online booking available

$245 - $275
Per Night

$1540 - $1750
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

$295 - $495
Per Night

$2065 - $5250
Per Week

Ho'olei #55-2 Luxurious New Wailea Rental Home

Wailea
Relax in this spectacular three bedroom deluxe accommodation. Beautiful decorations, with an invitin...
Condo 3 / 3.5 / 8

*
Online booking available

$4970 - $5460
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 - $318
Per Night

$1393 - $3490
Per Week

Wailea Ekahi 39D

Wailea
This luxury condo was designed to mirror a Balinese tree house. Completely remodeled with Hi-Tech A...
Condo 1 / 1 / 2

*
Online booking available

$280 - $340
Per Night

$1962 - $2520
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

$189 - $296
Per Night

$1323 - $2990
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 - $329
Per Night

$1575 - $2990
Per Week

Grand Champions #143 is a 3 BR 2 bath renovated golf cour...

Wailea
Grand Champions #143 is a 3 BR 2 bath renovated golf course view condo. Unit 143 at the Wailea Gran...
Condo 3 / 2 / 8

*
Online booking available

$2275 - $6050
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

$199 - $329
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

$189 - $296
Per Night

$1323 - $2790
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

$225 - $329
Per Night

$1575 - $2990
Per Week

Wailea Ekolu #303 - Quiet Park-Like Setting with Golf and...

Wailea
Wailea Ekolu #303 - Quiet Park-Like Setting with Golf and Ocean Views ! Great Spring 2015 Rates - P...
Condo 1 / 2 / 2

*
Online booking available

$209 - $209
Per Night

$1463 - $1463
Per Week

Stop! Look No Further! Palms at Wailea #1503 Ocean View B...

Wailea
Stop! Look No Further! Palms at Wailea #1503 Ocean View Best Location! The fabulous Keawakapu Beach...
Condo 2 / 2 / 4

*
Online booking available

$299 - $439
Per Night

$2093 - $4490
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 - $5460
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

 

More Getaway Locations and Properties