Wailea, Maui, Hawaii

Vacation Rentals in Wailea, Maui, Hawaii

Discover 25 vacation rental properties in Wailea, Maui. From 1 to 2 bedrooms. Average $584/night. 100% have pools.

25 verified listings Book securely on VRBO Prices updated March 2026

25 properties available

Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!

Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!

1 bed 2 baths
PoolA/CWiFiBalcony
$377/night
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Breathtaking New Remodeled Condo - Wailea Ekolu Village #401

Breathtaking New Remodeled Condo - Wailea Ekolu Village #401

2 beds 2 baths
PoolA/CWiFiBalcony
$311/night
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Stunning Remodeled 2 Bedroom - Wailea Ekolu #914

Stunning Remodeled 2 Bedroom - Wailea Ekolu #914

2 beds 2 baths
PoolA/CWiFiBalcony
$325/night
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Elegant Interiors & Spectacular Views at Wailea Elua #107 with Pristine Grounds

Elegant Interiors & Spectacular Views at Wailea Elua #107 with Pristine Grounds

2 beds
PoolA/CWiFiBalcony
$833/night
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Unforgettable Maui Escape: Experience Wailea Elua 1402, Your Oceanfront Haven!

Unforgettable Maui Escape: Experience Wailea Elua 1402, Your Oceanfront Haven!

1 bed 1 bath
PoolA/CWiFiBalcony
$572/night
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Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds

Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds

2 beds 2 baths
PoolA/CWiFiBalcony
$638/night
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OceanView Tranquility: Luxurious Condo with Spectacular Grounds - Elua #1104

OceanView Tranquility: Luxurious Condo with Spectacular Grounds - Elua #1104

2 beds
PoolA/CWiFiBalcony
$674/night
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Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508

Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508

2 beds
PoolA/CWiFiBalcony
$631/night
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Idyllic Retreat: Exquisitely Renovated Wailea Elua 801 -Serene Surroundings

Idyllic Retreat: Exquisitely Renovated Wailea Elua 801 -Serene Surroundings

2 beds 2 baths
PoolA/CWiFiBalcony
$744/night
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SPECIAL285/nt6/17-7/7 325/nt7/27-8/10,8/17-31 WaileaEkahi33A 1bd/2bth, Lux Condo

SPECIAL285/nt6/17-7/7 325/nt7/27-8/10,8/17-31 WaileaEkahi33A 1bd/2bth, Lux Condo

1 bed 2 baths
PoolA/CWiFiBalcony
$348/night
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Spacious Modern Haven Just Steps from the Beach - Wailea Elua #908 -Lush Grounds

Spacious Modern Haven Just Steps from the Beach - Wailea Elua #908 -Lush Grounds

2 beds 2 baths
PoolA/CWiFiBalcony
$748/night
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Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B

Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B

2 beds 2 baths
PoolA/CWiFiBalcony
$546/night
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Wailea Beach Villas PH504

Wailea Beach Villas PH504

2 beds 2 baths
PoolA/CWiFiBalcony
$978/night
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Amazing Ocean Views, AC in every room, remodeled, #504

Amazing Ocean Views, AC in every room, remodeled, #504

2 beds 2 baths
PoolA/CWiFiBalcony
$320/night
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Stunning Golf Course & Ocean Views - WAILEA GRAND CHAMPION #142

Stunning Golf Course & Ocean Views - WAILEA GRAND CHAMPION #142

1 bed 2 baths
PoolA/CWiFiBalcony
$210/night
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Beautiful Golf & Ocean Views - WAILEA GRAND CHAMPION #148

Beautiful Golf & Ocean Views - WAILEA GRAND CHAMPION #148

2 beds 2 baths
PoolA/CWiFiBalcony
$236/night
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Beautiful Wailea Condo - Wailea Ekolu #312

Beautiful Wailea Condo - Wailea Ekolu #312

1 bed 2 baths
PoolA/CWiFiBalcony
$251/night
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Luxury Wailea Condo - Enjoy Beautiful Ocean & Golf Views and Multi Zone AC.

Luxury Wailea Condo - Enjoy Beautiful Ocean & Golf Views and Multi Zone AC.

2 beds 2 baths
PoolA/CWiFiBalcony
$431/night
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Ocean Front, Luxury, Ground Floor, Polo Beach 102

Ocean Front, Luxury, Ground Floor, Polo Beach 102

2 beds 2 baths
PoolA/CWiFiBalcony
$853/night
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Luxurious & Spacious Ground Floor Gem with Panoramic Oceanview - Wailea Elua 305

Luxurious & Spacious Ground Floor Gem with Panoramic Oceanview - Wailea Elua 305

2 beds 2 baths
PoolA/CWiFiBalcony
$561/night
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Beautiful 2 Bedroom 2nd Floor Condo -Ocean Views - Wailea Elua Village #2202

Beautiful 2 Bedroom 2nd Floor Condo -Ocean Views - Wailea Elua Village #2202

2 beds 2 baths
PoolA/CWiFiBalcony
$531/night
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Mesmerizing Vistas - Oceanfront Treasure: Wailea Elua 1404 - Lush Surroundings

Mesmerizing Vistas - Oceanfront Treasure: Wailea Elua 1404 - Lush Surroundings

2 beds 2 baths
PoolA/CWiFiBalcony
$1,003/night
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Beautiful Ground Floor Condo 2 BDRM Condo- Wailea Elua #2501

Beautiful Ground Floor Condo 2 BDRM Condo- Wailea Elua #2501

2 beds 2 baths
PoolA/CWiFiBalcony
$702/night
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Luxurious Wailea Elua 1702 - Stunning Ocean Views and Unforgettable Memories

Luxurious Wailea Elua 1702 - Stunning Ocean Views and Unforgettable Memories

2 beds 2 baths
PoolA/CWiFiBalcony
$1,068/night
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Great Location - Beautiful Grounds - 2 Bedroom Two Bath - Wailea Elua #2106

Great Location - Beautiful Grounds - 2 Bedroom Two Bath - Wailea Elua #2106

2 beds 2 baths
PoolA/CWiFiBalcony
$712/night
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