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Beach Rentals - Wailea, HI

Wailea Beach Rentals

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Property owner typically means…
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  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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114 of 228 Trusted Wailea Rentals
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Wailea - Polo Beach Club - Groundfl...
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 of 5 stars 1 review
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Polo Beach 1or 2 Bdrm Oceanfront Pe...
2 Bedrooms, 2 Bathrooms, Sleeps 4
5 of 5 stars 2 reviews
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$649
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Polo Beach 1or 2 Bdrm Oceanfront Penthouse Condo
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Palms At Wailea 606
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 of 5 stars 5 reviews
20.0% off your stay
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$198
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Palms At Wailea 606
29 photos
Also consider
Beachfront Wailea Beauty at NEW LOWEST PRICES!!!
$170 - $250 / night
1 Bedroom, sleeps 4
2 Bathrooms
Grand Champions #103, Wailea, Maui
$149 - $199 / night
1 Bedroom, sleeps 4
2 Bathrooms
Palms at Wailea 2bd 2ba Sleeps 6 Great Rates!!
$199 - $299 / night
2 Bedrooms, sleeps 6
2 Bathrooms
Wailea Ekahi 44 C Everything New!
$295 - $355 / night
1 Bedroom, sleeps 4
2 Bathrooms
Palms at Wailea #1101 Great Ocean V...
2 Bedrooms, 2 Bathrooms, Sleeps 4
5 of 5 stars 24 reviews
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Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! 2/2 Great Rates!
34 photos
Palms at Wailea #2002
3 Bedrooms, 3 Bathrooms, Sleeps 8
5 of 5 stars 1 review
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10 photos
Wailea Orchid Villa - Panoramic Vie...
3 Bedrooms, 3 Bathrooms, Sleeps 8
5 of 5 stars 5 reviews
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Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba
32 photos
Elua Village # 701 - Luxury 2b/2b w...
2 Bedrooms, 2 Bathrooms, Sleeps 5
5 of 5 stars 11 reviews
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$395
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Elua Village # 701 - Luxury 2b/2b with Ocean View!
16 photos
Perfect Escape! Ho'Olei Dream -Supe...
3 Bedrooms, 4 Bathrooms, Sleeps 8
5 of 5 stars 4 reviews
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Perfect Escape! Ho'Olei Dream -Super Close to Pool
22 photos
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Awesome!, Ocean Views, Summer Sale...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 18 reviews
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Awesome!, Ocean Views, Summer Sale, $199/nt.!
19 photos
$200/nt 7/24-8/4-Wailea Ekahi 33A L...
1 Bedroom, 2 Bathrooms, Sleeps 5
5 of 5 stars 11 reviews
$50 off per night
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$200/nt 7/24-8/4-Wailea Ekahi 33A Lux Beach Resort
12 photos
Ho'olei with Grand Wailea Resort Ac...
3 Bedrooms, 4 Bathrooms, Sleeps 8
5 of 5 stars 1 review
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Ho'olei with Grand Wailea Resort Access & Views
45 photos
WAILEA ELUA, #1510
2 Bedrooms, 2 Bathrooms, Sleeps 4
5 of 5 stars 6 reviews
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16 photos
Ocean View, Remodeled, Stuff for th...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 4 reviews
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10 photos
Wailea Ekahi 7G Luxury Ocean Front...
1 Bedroom, 2 Bathrooms, Sleeps 3
5 of 5 stars 18 reviews
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Wailea Ekahi 7G Luxury Ocean Front S Maui Condo
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WAILEA ELUA, #1305^
3 Bedrooms, 3 Bathrooms, Sleeps 6
5 of 5 stars 10 reviews
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WAILEA ELUA, #1305^
16 photos
Aloha Kai Suite at Wailea Beach Vil...
3 Bedrooms, 3 Bathrooms, Sleeps 8
5 of 5 stars 66 reviews
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Aloha Kai Suite at Wailea Beach Villas PH 205
14 photos
Summer Special-Book 6 Nights, Get t...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 1 review
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Summer Special-Book 6 Nights, Get the 7th Free
23 photos
Wailea Ekahi 1B
1 Bedroom, 2 Bathrooms, Sleeps 4
4.5 of 5 stars 3 reviews
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18 photos
Bella Luna D302 Wailea Beach Villas
3 Bedrooms, 4 Bathrooms, Sleeps 6
5 of 5 stars 3 reviews
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Bella Luna D302 Wailea Beach Villas
76 photos
Modern, Renovated & Relaxing 2 Bedr...
2 Bedrooms, 2 Bathrooms, Sleeps 4
5 of 5 stars 3 reviews
1 night free with a 7 day stay
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Modern, Renovated & Relaxing 2 Bedroom 2 Bathroom
24 photos
Wailea Ekahi #16B
Studio, 1 Bathroom, Sleeps 2
5 of 5 stars 5 reviews
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19 photos
Palms at Wailea #1204 2 Bedroom 2 B...
2 Bedrooms, 2 Bathrooms, Sleeps 4
4 of 5 stars 14 reviews
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Palms at Wailea #1204 2 Bedroom 2 Bath Gorgeous Unit! Great Rates!
25 photos
Wailea Ekolu Spectacular 2 Bd 2.5 B...
2 Bedrooms, 3 Bathrooms, Sleeps 4
5 of 5 stars 9 reviews
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Wailea Ekolu Spectacular 2 Bd 2.5 Bath Deluxe Ocean View Townhouse Sleeps 4
42 photos
Modern and Spacious with Huge Tropi...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 4 reviews
1 night free with a 7 day stay
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Wailea Ekolu #1604
2 Bedrooms, 2 Bathrooms, Sleeps 4
5 of 5 stars 1 review
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Palms at Wailea #1606
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 of 5 stars 16 reviews
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Grand Champions #186
2 Bedrooms, 2 Bathrooms, Sleeps 4
5 of 5 stars 3 reviews
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Grand Champions #186
14 photos
Ocean View, Studio, Ekahi Condo 53E
Studio, 1 Bathroom, Sleeps 2
4.5 of 5 stars 7 reviews
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12 photos
Awesome Ocean View - Beautiful 2 BR...
2 Bedrooms, 3 Bathrooms, Sleeps 6
5 of 5 stars 1 review
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Grand Champions #165
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 of 5 stars 2 reviews
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WAILEA ELUA, #2303^
2 Bedrooms, 2 Bathrooms, Sleeps 5
5 of 5 stars 5 reviews
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Remodeled Ekolu condo with sweeping...
1 Bedroom, 2 Bathrooms, Sleeps 4
5 of 5 stars 1 review
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Grand Champions #36
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 of 5 stars 5 reviews
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Beautiful Ocean View Wailea Ekahi!
1 Bedroom, 2 Bathrooms, Sleeps 4
5 of 5 stars 8 reviews
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Owner Direct, Wailea Elua Oceanfron...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 20 reviews
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Palms at Wailea #604
2 Bedrooms, 2 Bathrooms, Sleeps 6
4.5 of 5 stars 4 reviews
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26 photos
Newly updated 2B/2B, lush tropical...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 13 reviews
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Newly updated 2B/2B, lush tropical grounds with ocean view pool and hot tub.
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Amazing Wailea GC#166, Remodeled, O...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 33 reviews
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AFFORDABLE - LAST MIN JUN 15-19 $12...
1 Bedroom, 1 Bathroom, Sleeps 2
5 of 5 stars 16 reviews
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AFFORDABLE - LAST MIN JUN 15-19 $120/NT + TX + CLG
25 photos
Wailea Grand Champions #50 is a 2 B...
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 of 5 stars 5 reviews
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Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 6.
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Enjoy a relaxing vacation right on the beach in Wailea. Spend your days in the sun and sand, then come home to your beach vacation rental, equipped with all the comforts of home.
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Book Online(13)
Rental communities
Ekahi Vil... (50)
Grand Cha... (35)
Wailea Be... (27)
The Palms... (23)
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Hoolei (17)
Wailea Ek... (11)
Polo Beach... (4)
Makena Sur... (2)
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    2 Bedrooms, 2 Baths
    $195/night+
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    1 Bedroom, 2 Baths
    $195/night+
  • Palms 1507- 2B/2B Spectacular Remodeled Ocean View Unit
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