Wailea Vacation Rental Getaways


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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 - $255
Per Night

$1365 - $1785
Per Week

Summer Special! Wailea Ekahi 46F- Spacious 2 BR 2 Bath Co...

Wailea
Summer Special! Wailea Ekahi 46F- Spacious 2 BR 2 Bath Condo in Wailea! Wailea Ekahi - Nicely appoi...
Condo 2 / 2 / 6

*
Online booking available

$252 - $380
Per Night

$1575 - $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

$1925 - $4490
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 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

Grand Champions 8 - Top Floor Private Lanai

Wailea
Grand Champions 8 is a top floor tropical delight with lush foliage surrounding the lanai for privac...
Condo 2 / 2 / 4

*
Online booking available

$195 - $583
Per Night

$1368 - $4082
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

Grand Champions 139 - Renovated Two Bedroom Condo

Wailea
Beautifully decorated and fully renovated two bedroom condominium with garden, some ocean and mounta...
Condo 2 / 2 / 4

*
Online booking available

$209 - $614
Per Night

$1463 - $4300
Per Week

Wailea Ekolu 1106 - Modern Updates Incredible Views

Wailea
Enjoy views of Kahoolawe, Molokini and Lana’i all from this condo’s wonderful location. Vaulted ceil...
Condo 2 / 2 / 4

*
Online booking available

$273 - $739
Per Night

$1909 - $5171
Per Week

Palms at Wailea Unit #2305 Quiet and Very Private! Summer...

Wailea
Palms at Wailea Unit #2305 Quiet and Very Private! Summer Special $169 We are pleased that our prop...
Condo 1 / 2 / 2

*
Online booking available

$179 - $427
Per Night

$1253 - $2990
Per Week

Wailea Ekolu #407 Completely Remodeled with Panoramic Oce...

Wailea
Wailea Ekolu #407 Completely Remodeled with Panoramic Ocean Views. Sleeps 2 Wailea Ekolu Unit 407 i...
Condo 1 / 2 / 2

*
Online booking available

$225 - $427
Per Night

$1575 - $2990
Per Week

Wailea Ekolu 1610 - Ocean View Renovated 2 Bedroom

Wailea
This spectacular two bedroom town home has been renovated throughout. The upstairs living area has a...
Condo 2 / 2.5 / 5

*
Online booking available

$273 - $739
Per Night

$1909 - $5171
Per Week

Grand Champions 65 - Perfect for a Small Family

Wailea
Grand Champions 65 is perfect for 2 couples or a family of four. A tropical atmosphere greets you as...
Condo 2 / 2 / 4

*
Online booking available

$209 - $614
Per Night

$1463 - $4300
Per Week

Palms at Wailea 1606 - Spacious 2 Bedroom Condo

Wailea
A spacious two bedroom two bath condominium in beautiful Wailea. A partial ocean view, BBQ grill ...
Condo 2 / 2 / 6

*
Online booking available

$177 - $529
Per Night

$1241 - $3701
Per Week

Palms at Wailea #1005 Panoramic Ocean Views 1Bd 2Ba Sleep...

Wailea
Palms at Wailea #1005 Panoramic Ocean Views 1Bd 2Ba Sleeps 4 Great Rates! The fabulous Keawakapu Be...
Condo 1 / 2 / 4

*
Online booking available

$225 - $499
Per Night

$1575 - $3490
Per Week

Grand Champions 102 - Stunning Sunrise Views

Wailea
Luxury inside and out awaits you at this beautiful condo! The balcony overlooks Old Blue golf course...
Condo 2 / 2 / 4

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
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 310 - Ocean View Condo on Golf Course

Wailea
Wailea Ekolu #310 is a Second Floor, Two bedroom Two bath, Ocean View Condo on the 'Old Blue' Wailea...
Condo 2 / 2 / 4

*
Online booking available

$286 - $634
Per Night

$2002 - $4441
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

$203 - $280
Per Night

$1134 - $1960
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

Ho'olei 39-3 - Spacious Upscale Townhouse Stunning Views

Wailea
Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living sp...
Condo 3 / 3.5 / 8

*
Online booking available

$727 - $1944
Per Night

$5087 - $13608
Per Week

Wailea Ekahi 4E - Garden View 2nd Floor Condo

Wailea
Wailea Ekahi Village 4E Second floor condominium is adjacent to a landscaped ravine and has beautifu...
Condo 1 / 1 / 2

*
Online booking available

$195 - $583
Per Night

$1368 - $4082
Per Week

Grand Champions 186 - 2nd Floor Condo Overlooking Pool

Wailea
Grand Champions 186 is located on the second floor and overlooks one of the 2 pools on property. Fea...
Condo 2 / 2 / 4

*
Online booking available

$210 - $591
Per Night

$1470 - $4137
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

$189 - $456
Per Night

$1323 - $3190
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 / 6

*
Online booking available

$249 - $570
Per Night

$1743 - $3990
Per Week

 

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