Wailea Vacation Rental Getaways


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  • Pets Allowed
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  • Pool Access
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  • Smoking allowed
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  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
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  • Lake View
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  • 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

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

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

$295 - $380
Per Night

$2065 - $2660
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 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 - $2170
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 - $305
Per Night

$1645 - $1960
Per Week

Wailea Ekolu #501 Panoramic Ocean View, 2Bd/2Ba, A/C, Sle...

Wailea
Wailea Ekolu #501 Panoramic Ocean View, 2Bd/2Ba, A/C, Sleeps 4, Great Rates! Wailea Ekolu is one of...
Condo 2 / 2 / 4

*
Online booking available

$215 - $593
Per Night

$1505 - $4150
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

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 - $399
Per Night

$1323 - $2790
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

$199 - $499
Per Night

$1393 - $3490
Per Week

Grand Champions 123 - Renovated 3-Bedroom

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 - $810
Per Night

$1449 - $5670
Per Week

Palms at Wailea #305 A/C Throughout, Close to Pool, Nicel...

Wailea
Palms at Wailea #305 A/C Throughout, Close to Pool, Nicely Appointed The fabulous Keawakapu Beach i...
Condo 2 / 2 / 6

*
Online booking available

$225 - $493
Per Night

$1575 - $3450
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 - $955
Per Night

$5670 - $6685
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

$199 - $536
Per Night

$1393 - $3750
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

Wailea Ekolu #205 Ocean View, Ground Floor, 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 #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 - $240
Per Night

$1190 - $1575
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 - $707
Per Night

$2065 - $4950
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 - $427
Per Night

$1393 - $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 #186 2Br/2Ba Near The Pool, Great Locatio...

Wailea
Grand Champions #186 2Br/2Ba Near The Pool, Great Location Remodeled Kitchen. Spring Saver 2017 Spe...
Condo 2 / 2 / 4

*
Online booking available

$260 - $305
Per Night

$1645 - $1960
Per Week

Wailea Ekolu #1610

Wailea
Spring Saver Rates 2017 - Book Early ! Promo Code: SPRINGSAVER! This spectacular two bedroom town h...
Condo 2 / 2.5 / 5

*
Online booking available

$335 - $385
Per Night

$2205 - $2485
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

$304 - $649
Per Night

$2128 - $4540
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

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

Wailea
Palms at Wailea #1606 Spacious 2Br/2Ba - Great Rates - Free Wifi ! Special Spring Saver Rates 2017 ...
Condo 2 / 2 / 6

*
Online booking available

$245 - $285
Per Night

$1540 - $1820
Per Week

 

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