Wailea Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

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

Wailea
With a large open-air balcony, spacious living area, and luxurious master suite, this condo brings y...
Condo 1 / 2 / 4

*
Online booking available

$284 - $846
Per Night

$1988 - $5925
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

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

$249 - $636
Per Night

$1743 - $4450
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

$189 - $345
Per Night

$1323 - $2415
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

Spacious and Elegant 2b/2B View Condo

Wailea
Unit 1507 is a beautifully renovated condo with a gorgeous ocean view. An end unit, located in the c...
Condo 2 / 2 / 4

*
Online booking available

$279 - $641
Per Night

$1953 - $4490
Per Week

Grand Champions 089

Wailea
Grand Champions two bedroom condo with fabulous views of the golf course. This condo is currently un...
Condo 2 / 2 / 6

*
Online booking available

$440 - $550
Per Night

$3080 - $3850
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 1610 - 2 Bedrooms, Renovated, Ocean View, 2 ...

Wailea
Gaze at the sea from your private lanai at this stunning 2-bedroom, 2-story townhome! Treat yourself...
Condo 2 / 2.5 / 5

*
Online booking available

$265 - $772
Per Night

$1855 - $5405
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

$225 - $463
Per Night

$1575 - $3240
Per Week

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

Wailea
You’ve hit the jackpot when you vacation at Grand Champions 134. With panoramic views that will take...
Condo 3 / 2 / 6

*
Online booking available

$275 - $819
Per Night

$1925 - $5731
Per Week

Palms at Wailea 702 Upstairs Garden View 1B/2B Sleeps 4.

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

$169 - $427
Per Night

$1183 - $2990
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 Ekahi 4E - 1 Bedroom, Garden View 2nd Floor, Acces...

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

*
Online booking available

$175 - $610
Per Night

$1225 - $4268
Per Week

Grand Champions 138, 2 Bedrooms, Remodeled, 2 Master Suit...

Wailea
Enjoy lush tropical views and all the perks of a resort just a mile from the beach! Boasting high ce...
Condo 2 / 2 / 5

*
Online booking available

$175 - $610
Per Night

$1225 - $4268
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 - $521
Per Night

$1470 - $3650
Per Week

Ho'olei 39-3 - 3 Bedroom, Spacious Upscale Condo, 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

$740 - $2372
Per Night

$5180 - $16604
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

$215 - $593
Per Night

$1505 - $4150
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

Grand Champions #45 is a 2bd 2ba Ocean view condo that Sl...

Wailea
Grand Champions #45 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 #205 2B/2B - Luxurious, Spacious, Fantast...

Wailea
Palms at Wailea #205 2B/2B - Luxurious, Spacious, Fantastic Location! The fabulous Keawakapu Beach ...
Condo 2 / 2 / 6

*
Online booking available

$289 - $641
Per Night

$2023 - $4490
Per Week

Wailea Ekahi 17E - 1 Bedroom, Ocean View Oversized Lanai,...

Wailea
The beauty of sand and sparkling waters and the warm Hawaii sun is calling your name! Wailea Ekahi 1...
Condo 1 / 2 / 2

*
Online booking available

$218 - $726
Per Night

$1526 - $5083
Per Week

Wailea Ekahi 17D - 1 Bedroom, 2nd Floor Panoramic Ocean V...

Wailea
Panoramic views of the Pacific Ocean, outer islands, and lush tropical foliage flood your lanai, liv...
Condo 1 / 2 / 4

*
Online booking available

$265 - $772
Per Night

$1855 - $5405
Per Week

Grand Champions 8 - 2 Bedrooms, Top Floor Private Lanai, ...

Wailea
Palm trees swaying in the breeze, tropical air filling your senses, and a great ocean view are waiti...
Condo 2 / 2 / 4

*
Online booking available

$180 - $636
Per Night

$1260 - $4451
Per Week

Wailea Ekahi 38B - Charming 1 Bedroom Condo, Access to 4 ...

Wailea
The ocean view will indulge your senses at Wailea Ekahi 38B! This beautifully renovated first-floor...
Condo 1 / 2 / 4

*
Online booking available

$204 - $681
Per Night

$1428 - $4765
Per Week

 

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