Wailea, Hawaii

Vacation Rentals in Wailea, Hawaii

Discover 291 vacation rental properties in Wailea. From 1 to 4 bedrooms. Average $535/night. 100% have pools.

291 verified listings Book securely on VRBO Prices updated March 2026

291 properties available

Premier Beachfront Wailea Elua 2 Bdrm+2 Ba Condominium #1904

Premier Beachfront Wailea Elua 2 Bdrm+2 Ba Condominium #1904

2 beds 2 baths
PoolA/CWiFiBalcony
$898/night
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!

14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!

1 bed 2 baths
PoolA/CWiFiBalcony
$634/night
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Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!

Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!

2 beds 2 baths
PoolA/CWiFiBalcony
$889/night
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Direct Ocean Front Polo Beach 805!

Direct Ocean Front Polo Beach 805!

2 beds 2 baths
PoolA/CWiFiBalcony
$718/night
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Palms at Wailea #1903 Luxe Remodel, Ground Floor, Walk to Beach and Shops!

Palms at Wailea #1903 Luxe Remodel, Ground Floor, Walk to Beach and Shops!

2 beds 2 baths
PoolA/CWiFiBalcony
$391/night
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Wailea Ekolu #503 Panoramic Ocean View, Great Location near Ulua Beach, Wifi

Wailea Ekolu #503 Panoramic Ocean View, Great Location near Ulua Beach, Wifi

2 beds 2 baths
PoolA/CWiFiBalcony
$312/night
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Wailea Ekahi Village 9A - Newly Updated!

Wailea Ekahi Village 9A - Newly Updated!

1 bed 1 bath
PoolA/CWiFiBalcony
$314/night
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Email for summer specials! Close to the ocean! Hear the waves from the lanai!

Email for summer specials! Close to the ocean! Hear the waves from the lanai!

1 bed 1 bath
PoolA/CWiFiBalcony
$306/night
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Wailea Ekahi #53-C Hawaiian Beachfront, AC throughout, Easy Pool Access, Wifi

Wailea Ekahi #53-C Hawaiian Beachfront, AC throughout, Easy Pool Access, Wifi

2 beds 2 baths
PoolA/CWiFiBalcony
$447/night
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Wailea Ekahi 53D, breathtaking ocean views!

Wailea Ekahi 53D, breathtaking ocean views!

1 bed 1 bath
PoolA/CWiFiBalcony
$288/night
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Beautiful Listing! Fully Renovated! STUNNING VIEWS!! Elua 2305

Beautiful Listing! Fully Renovated! STUNNING VIEWS!! Elua 2305

2 beds 2 baths
PoolA/CWiFiBalcony
$720/night
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Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi

Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi

1 bed 2 baths
PoolA/CWiFiBalcony
$293/night
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Peaceful Wailea Oasis Ekahi 47E

Peaceful Wailea Oasis Ekahi 47E

1 bed 2 baths
PoolA/CWiFiBalcony
$241/night
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Stunning Remodel, Fantastic Lower Village Location, 1 Minute to Pool & Beach! 6C

Stunning Remodel, Fantastic Lower Village Location, 1 Minute to Pool & Beach! 6C

1 bed 2 baths
PoolA/CWiFiBalcony
$453/night
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Palms at Wailea #205 Fully Remodeled, Ground Floor Unit, Shared Hot Tub, A/C

Palms at Wailea #205 Fully Remodeled, Ground Floor Unit, Shared Hot Tub, A/C

2 beds 2 baths
PoolA/CWiFiBalcony
$353/night
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Palms at Wailea #1503 Look No Further, Best Location, Near Pool and Beaches

Palms at Wailea #1503 Look No Further, Best Location, Near Pool and Beaches

2 beds 2 baths
PoolA/CWiFiBalcony
$436/night
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Grand Champions #45, Great Rates, Ocean view condo, A/C, Shared Hot Tub

Grand Champions #45, Great Rates, Ocean view condo, A/C, Shared Hot Tub

2 beds 2 baths
PoolA/CWiFiBalcony
$316/night
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Palms at Wailea #1508 The Ultimate Condo at the Palms,Great Location on Maui

Palms at Wailea #1508 The Ultimate Condo at the Palms,Great Location on Maui

2 beds 2 baths
PoolA/CWiFiBalcony
$527/night
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Luxury Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.

Luxury Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.

2 beds 2 baths
PoolA/CWiFiBalcony
$378/night
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Spectacular Views and Prime Location! Oceanfront at Great Rates!! PB 502

Spectacular Views and Prime Location! Oceanfront at Great Rates!! PB 502

2 beds 2 baths
PoolA/CWiFiBalcony
$570/night
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2 bedroom, 2 bath family friendly Grand Champions 130!

2 bedroom, 2 bath family friendly Grand Champions 130!

2 beds 2 baths
PoolA/CWiFiBalcony
$273/night
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Grand Champions 32: 2 BR, 2 BA Condominium in Wailea, Sleeps 6

Grand Champions 32: 2 BR, 2 BA Condominium in Wailea, Sleeps 6

2 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior

Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior

1 bed 2 baths
PoolA/CWiFiBalcony
$500/night
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K B M Resorts: Grand Champions GCH-134, Upgraded 3 Bd w/Wrap Around Large Lanai, Includes Rental Car

K B M Resorts: Grand Champions GCH-134, Upgraded 3 Bd w/Wrap Around Large Lanai, Includes Rental Car

3 beds 2 baths
PoolA/CWiFiBalcony
$780/night
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Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach

Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach

1 bath
PoolA/CWiFiBalcony
$305/night
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Treetop Studio 2nd floor, corner unit

Treetop Studio 2nd floor, corner unit

1 bath
PoolA/CWiFiBalcony
$145/night
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TOP FLOOR CORNER PRIVATE STUDIO, AFFORDABLE WAILEA, WALK TO BEACH

TOP FLOOR CORNER PRIVATE STUDIO, AFFORDABLE WAILEA, WALK TO BEACH

1 bath
PoolA/CWiFiBalcony
$159/night
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🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈

🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈

1 bed 2 baths
PoolA/CWiFiBalcony
$265/night
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Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa

Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa

1 bed 2 baths
PoolA/CWiFiBalcony
$180/night
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Palms at Wailea #1803 Large Private Lanai, Spacious Unit, Wifi Great Location

Palms at Wailea #1803 Large Private Lanai, Spacious Unit, Wifi Great Location

1 bed 2 baths
PoolA/CWiFiBalcony
$262/night
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Wailea Ekahi 36E! One of the best locations in Wailea.

Wailea Ekahi 36E! One of the best locations in Wailea.

1 bed 2 baths
PoolA/CWiFiBalcony
$236/night
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Stunning Ocean and Fairway Views! Top Floor! Wailea Ekolu 208

Stunning Ocean and Fairway Views! Top Floor! Wailea Ekolu 208

1 bed 2 baths
PoolA/CWiFiBalcony
Price on request
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Stunning views with walking distance to the beach! Wailea Ekahi 49F.

Stunning views with walking distance to the beach! Wailea Ekahi 49F.

1 bed 1 bath
PoolA/CWiFiBalcony
$231/night
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Incredible Ocean View! ... 5 Star Reviews ... Hoʻokipa at Wailea Ekolu Village!

Incredible Ocean View! ... 5 Star Reviews ... Hoʻokipa at Wailea Ekolu Village!

1 bed 2 baths
PoolA/CWiFiBalcony
$349/night
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Grand Champions #48 Stunning 180 Degree Ocean Views. Top Floor Paradise Home

Grand Champions #48 Stunning 180 Degree Ocean Views. Top Floor Paradise Home

2 beds 2 baths
PoolA/CWiFiBalcony
$284/night
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CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

1 bed 1 bath
PoolA/CWiFiBalcony
$199/night
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Enjoy the Amazing View and have a Mai Tai too!

Enjoy the Amazing View and have a Mai Tai too!

1 bed 2 baths
PoolA/CWiFiBalcony
$352/night
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Perfect Couple Retreat! Stylish Renovated Top Floor Ocean View Condo

Perfect Couple Retreat! Stylish Renovated Top Floor Ocean View Condo

1 bed 2 baths
PoolA/CWiFiBalcony
$211/night
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Wailea Ekahi #16-C Ground Floor Unit Near Keawakapu Beach, Wifi, Full A/C

Wailea Ekahi #16-C Ground Floor Unit Near Keawakapu Beach, Wifi, Full A/C

1 bed 2 baths
PoolA/CWiFiBalcony
$414/night
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5 Star Ocean View, Beach House Chic, Ask to see Video tour!

5 Star Ocean View, Beach House Chic, Ask to see Video tour!

1 bed 2 baths
PoolA/CWiFiBalcony
$255/night
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Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!

1 bed 2 baths
PoolA/CWiFiBalcony
$229/night
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$200 SPRING SALE!Great view - close to beach! Fully remodeled!Sleeps 5! Bldg 30!

$200 SPRING SALE!Great view - close to beach! Fully remodeled!Sleeps 5! Bldg 30!

1 bed 1 bath
PoolA/CWiFiBalcony
$344/night
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Wailea Ekolu #105 Scenic Ocean View, Great Location, Near Beaches, Full AC

Wailea Ekolu #105 Scenic Ocean View, Great Location, Near Beaches, Full AC

2 beds 2 baths
PoolA/CWiFiBalcony
$382/night
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Prime Location! GC138!

Prime Location! GC138!

2 beds 2 baths
PoolA/CWiFiBalcony
$255/night
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Wailea Ekahi 17E | Resort Level Amenities!

Wailea Ekahi 17E | Resort Level Amenities!

1 bed 2 baths
PoolA/CWiFiBalcony
$203/night
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COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

2 beds 1 bath
PoolA/CWiFiBalcony
$351/night
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Wailea Ekahi Studio #48-D Gorgeous Studio, Keawakapu Beach

Wailea Ekahi Studio #48-D Gorgeous Studio, Keawakapu Beach

1 bath
PoolA/CWiFiBalcony
$276/night
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Charming Wailea Ekahi Condominium

Charming Wailea Ekahi Condominium

1 bed 2 baths
PoolA/CWiFiBalcony
$281/night
View Details → Book on VRBO

Showing 48 of 291 properties

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