Wailea Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Wailea Ekolu #105 Scenic Ocean View, Great Location, Slee...

Wailea
Wailea Ekolu #105 Scenic Ocean View, Great Location, Sleeps 4 Wailea Ekolu has several lovely pool ...
Condo 2 / 2 / 4

*
Online booking available

$203 - $607
Per Night

$1422 - $4250
Per Week

Grand Champions 134 - Renovated 3-Bedroom, Pool, Tennis

Wailea
Grand Champions 134 is located in a quiet setting in Wailea. Large green belts, manicured grounds, a...
Condo 3 / 2 / 6

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
Per Week

Wailea Ekahi 17E - Ocean View Oversized Lanai

Wailea
This condominium home has been beautifully upgraded throughout and boasts a wonderful kitchen, dinin...
Condo 1 / 2 / 2

*
Online booking available

$282 - $770
Per Night

$1973 - $5389
Per Week

Wailea Ekahi 32B - Ocean View Access to 4 Pools

Wailea
Enjoy the ocean view down the green belt from the covered lanai! BBQ with the gas grill or cook in t...
Condo 1 / 2 / 2

*
Online booking available

$321 - $816
Per Night

$2244 - $5715
Per Week

Grand Champions 102 - Stunning Sunrise Views

Wailea
Luxury inside and out awaits you at this beautiful condo! The lanai overlooks Old Blue Golf Course, ...
Condo 2 / 2 / 4

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
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 - $484
Per Night

$1575 - $3390
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 - $427
Per Night

$1393 - $2990
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

Grand Champions 49 - Spacious Lanai Garden View

Wailea
Grand Champions 49 is perfect for couples or a family of four. A cool clean atmosphere greets you as...
Condo 2 / 2 / 4

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
Per Week

Wailea Ekahi 35B - 2 Level Condo Walk to Beach

Wailea
Wailea Ekahi Village 35B is where you want to be. It is the paradise you have been looking for. Walk...
Condo 2 / 2.5 / 4

*
Online booking available

$321 - $816
Per Night

$2244 - $5715
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

$196 - $593
Per Night

$1369 - $4150
Per Week

Ho'olei 55-2 - Deluxe 3 Bedroom Townhouse Large Lanai

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

*
Online booking available

$641 - $1788
Per Night

$4487 - $12519
Per Week

Grand Champions 181 - Spacious Remodeled 1-Bedroom

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

$127 - $360
Per Night

$890 - $2519
Per Week

Grand Champions 132 - Chic and Charming Top Floor 1 Bedro...

Wailea
Completely remodeled in 2017 in chic mid-20th-Century decor, this Wailea condo is the ideal hideaway...
Condo 1 / 2 / 2

*
Online booking available

$195 - $583
Per Night

$1368 - $4082
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

$189 - $463
Per Night

$1323 - $3240
Per Week

Grand Champions 122 - Remodeled Kitchen & Bath

Wailea
Made just for 2, this beautiful condo with views of the Haleakala Mountains is the ideal place for y...
Condo 1 / 2 / 2

*
Online booking available

$168 - $498
Per Night

$1177 - $3484
Per Week

Wailea Ekolu 1604 - 2nd Floor Two Bedroom Condo

Wailea
A Second Floor, Two bedroom Two bath condo with garden and peek-a-boo ocean views. Our guests are we...
Condo 2 / 2 / 4

*
Online booking available

$209 - $614
Per Night

$1463 - $4300
Per Week

Palms at Wailea #1803 Large Private Lanai, Spacious, Grea...

Wailea
Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4 The fabulous Keawakap...
Condo 1 / 2 / 4

*
Online booking available

$159 - $427
Per Night

$1113 - $2990
Per Week

Wailea Elua 1904 - 2 Bedroom Remodeled on the Beach

Wailea
Newly remodeled, Two bedroom / Two bathroom, second floor condominium right on the Beach! It is perf...
Condo 2 / 2 / 4

*
Online booking available

$577 - $1633
Per Night

$4039 - $11431
Per Week

Grand Champions 141 - Nicely Updated 1 Bedroom, 2 Bath Condo

Wailea
A tropical atmosphere greets you as you enter Grand Champions 141. A beautifully decorated ground fl...
Condo 1 / 2 / 4

*
Online booking available

$168 - $498
Per Night

$1177 - $3484
Per Week

Grand Champions 165 - Access to Pools & Jacuzzi

Wailea
The inviting tropical decor in Grand Champions 165 greets you as you enter. Beautiful new tile flows...
Condo 2 / 2 / 4

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
Per Week

Wailea Ekahi 41B - Ground Floor Beach Access

Wailea
Wailea Ekahi 41B is a lovely ground floor condominium furnished with a King bed in the master bedroo...
Condo 1 / 2 / 2

*
Online booking available

$209 - $614
Per Night

$1463 - $4300
Per Week

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 - $530
Per Night

$2975 - $3710
Per Week

Grand Champions 54 - Upgraded Kitchen & Baths

Wailea
All New Upgraded Kitchen and Baths. Grand Champions 54 offers a large 54" flat screen TV, DVD player...
Condo 1 / 2 / 4

*
Online booking available

$168 - $498
Per Night

$1177 - $3484
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

$229 - $750
Per Night

$1603 - $5250
Per Week

 

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