Vacation Rentals in Wailea, Hawaii

50 Properties Available

Oceanfront 3BR villa w/ private lanai and Wailea Beach access Villa
Oceanfront 3BR villa w/ private lanai and Wailea Beach access
$4145 / night
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WELCOME TO OUR BEAUTIFULLY REMODELED & REDECORATED SEA LA VIE L510 AT WAILEA BEACH VILLAS! Villa
WELCOME TO OUR BEAUTIFULLY REMODELED & REDECORATED SEA LA VIE L510 AT WAILEA BEACH VILLAS!
$2944 / night
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ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8! Villa
ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!
$2552 / night
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FRESHLY RENOVATED, SPECTACULAR OCEAN VIEWS, ULTRA-LUXE BLUE OCEAN SUITE H401 Villa
FRESHLY RENOVATED, SPECTACULAR OCEAN VIEWS, ULTRA-LUXE BLUE OCEAN SUITE H401
$2411 / night
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ULTRA LUXURY SEASPIRIT 811 3 Br\/4Ba RESIDENCE VILLA, HOT TUB SPA SLEEPS 8! Villa
ULTRA LUXURY SEASPIRIT 811 3 Br\/4Ba RESIDENCE VILLA, HOT TUB SPA SLEEPS 8!
$2373 / night
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Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBM Condo
Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBM
$2150 / night
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Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3 Villa
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
$2081 / night
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Wrap-Around Ocean Views | Wailea Beach Villas PH301 Condo
Wrap-Around Ocean Views | Wailea Beach Villas PH301
$2007 / night
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BEACHFRONT OCEAN VIEWS WAILEA CONTEMPORARY ELEGANT Condo
BEACHFRONT OCEAN VIEWS WAILEA CONTEMPORARY ELEGANT
$1995 / night
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Ho'olei Villas | Wailea Kapili Private vacation home
Ho'olei Villas | Wailea Kapili
$1818 / night
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Makena Surf F305 | Top-Floor Oceanfront, Resort Pools & Wildlife Viewing Condo
Makena Surf F305 | Top-Floor Oceanfront, Resort Pools & Wildlife Viewing
$1739 / night
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Exceptional Design & Ocean Views Condo
Exceptional Design & Ocean Views
$1719 / night
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Cool Wailea Villa with Arcade Machine Condo
Cool Wailea Villa with Arcade Machine
$1718 / night
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Stunning Ocean View Wailea Beach Villa- Book & Save Villa
Stunning Ocean View Wailea Beach Villa- Book & Save
$1695 / night
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Wailea Point Executive 2 Bedroom/3 Bath Oceanview Vacation Home Condo
Wailea Point Executive 2 Bedroom/3 Bath Oceanview Vacation Home
$1601 / night
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HO'OLEI #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10-METICULOUS CLEANING Condo
HO'OLEI #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10-METICULOUS CLEANING
$1569 / night
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Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium Condo
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
$1538 / night
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Oceanfront Maui condo w/ lanai and island views Condo
Oceanfront Maui condo w/ lanai and island views
$1481 / night
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Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill Condo
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
$1417 / night
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Oceanfront Maui condo w/ sunset lanai and pool access Condo
Oceanfront Maui condo w/ sunset lanai and pool access
$1381 / night
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Wailea Elua Village 905 | Ground Floor, Steps to Beach, 2 Pools & Pickleball Condo
Wailea Elua Village 905 | Ground Floor, Steps to Beach, 2 Pools & Pickleball
$1328 / night
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Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier Private vacation home
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier
$1166 / night
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Wailea Elua Village 1703 Condo
Wailea Elua Village 1703
$1149 / night
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Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center Private vacation home
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
$1099 / night
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The Sweet Spot - Wailea Elua 3-Bdr\/3-Bath Beachfront Paradise Townhouse #1004 Condo
The Sweet Spot - Wailea Elua 3-Bdr\/3-Bath Beachfront Paradise Townhouse #1004
$1050 / night
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Wailea Ekahi 29C, Ocean View, Steps away from the pool Condo
Wailea Ekahi 29C, Ocean View, Steps away from the pool
$1041 / night
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Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior Condo
Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior
$1031 / night
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Makena Surf B305 | Oceanfront, Pools, Hot Tub, Turtle Snorkeling & Tennis Courts Condo
Makena Surf B305 | Oceanfront, Pools, Hot Tub, Turtle Snorkeling & Tennis Courts
$1012 / night
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Makena Surf E302 | Top-Floor Ocean Views, Whale Watching, Pools and Hot Tub Condo
Makena Surf E302 | Top-Floor Ocean Views, Whale Watching, Pools and Hot Tub
$950 / night
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Makena Surf F104 - Oceanfront condo Condo
Makena Surf F104 - Oceanfront condo
$950 / night
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Makena Surf F112 - Oceanfront Platinum condo! Condo
Makena Surf F112 - Oceanfront Platinum condo!
$929 / night
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$425 SPRING SALE! Best Location!Brand New Remodel! Bldg 32 Condo
$425 SPRING SALE! Best Location!Brand New Remodel! Bldg 32
$924 / night
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Ocean & Golf Course View 3 Bed - Close to the pool! Condo
Ocean & Golf Course View 3 Bed - Close to the pool!
$919 / night
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Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the Beach Condo
Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the Beach
$887 / night
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Wailea Elua Village | 708 Condo
Wailea Elua Village | 708
$852 / night
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Maui...True Paradise! Walking to white sandy beaches! Condo
Maui...True Paradise! Walking to white sandy beaches!
$832 / night
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Wailea Elua Village 805 Condo
Wailea Elua Village 805
$740 / night
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Makena Surf B106 - Oceanfront Platinum condo! Condo
Makena Surf B106 - Oceanfront Platinum condo!
$733 / night
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Wailea Ekahi Village | 3A Condo
Wailea Ekahi Village | 3A
$721 / night
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Wailea Ekahi Village 30D | Ocean View Haven by the Beach, 4 Pools & Pickleball Condo
Wailea Ekahi Village 30D | Ocean View Haven by the Beach, 4 Pools & Pickleball
$686 / night
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Palms at Wailea Garden Deluxe Villas 2 BD 2 BA Condo
Palms at Wailea Garden Deluxe Villas 2 BD 2 BA
$661 / night
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3BD Golf Haven - Great for Families Condo
3BD Golf Haven - Great for Families
$639 / night
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Incredibly Large Polynesian Style Villa in Wailea Condo
Incredibly Large Polynesian Style Villa in Wailea
$638 / night
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Stunning unit! Beautiful Remodel! Ocean Views! Ekahi 5E Condo
Stunning unit! Beautiful Remodel! Ocean Views! Ekahi 5E
$636 / night
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Makena Surf E105 - Oceanfront condo Condo
Makena Surf E105 - Oceanfront condo
$632 / night
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Beautiful, Palms At Wailea Condo #608- 2BR/2BA,GREAT LOCATION! SPECIAL Rates Condo
Beautiful, Palms At Wailea Condo #608- 2BR/2BA,GREAT LOCATION! SPECIAL Rates
$601 / night
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Wailea Elua Village 1501 Condo
Wailea Elua Village 1501
$571 / night
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Spacious Ground-Floor Beach Retreat -White Sandy Beaches of Wailea! Condo
Spacious Ground-Floor Beach Retreat -White Sandy Beaches of Wailea!
$559 / night
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Elevated Ocean Views | Walk to the Beach Condo
Elevated Ocean Views | Walk to the Beach
$554 / night
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Wailea Ekahi Village | 23C Condo
Wailea Ekahi Village | 23C
$550 / night
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