Wailea-Makena, Hawaii

Vacation Rentals in Wailea-Makena, Hawaii

Discover 60 vacation rental properties in Wailea-Makena. From 1 to 4 bedrooms. Average $551/night. 100% have pools.

60 verified listings Book securely on VRBO Prices updated March 2026

60 properties available

Steps to Ocean View Pool, Walk to Beach

Steps to Ocean View Pool, Walk to Beach

1 bed 2 baths
PoolA/CWiFiBalcony
$292/night
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Wailea Point 3203 - 30nt+ Luxury Wailea Resort Property

Wailea Point 3203 - 30nt+ Luxury Wailea Resort Property

2 beds 2 baths
PoolA/CWiFiBalcony
$466/night
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160KReno-Stunning Palms in Wailea Condo-Beach/Golf

160KReno-Stunning Palms in Wailea Condo-Beach/Golf

1 bed 2 baths
PoolA/CWiFiBalcony
$286/night
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Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C

Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C

1 bed 2 baths
PoolA/CWiFiBalcony
$340/night
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Upgraded ocean view condo in a prime South Kihei location.

Upgraded ocean view condo in a prime South Kihei location.

1 bed 1 bath
PoolA/CWiFiBalcony
$189/night
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Listen to the birds chirp!

Listen to the birds chirp!

1 bath
PoolA/CWiFiBalcony
$150/night
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Gorgeous Maui Condo w/ Oceans Views

Gorgeous Maui Condo w/ Oceans Views

1 bed 2 baths
PoolA/CWiFiBalcony
$295/night
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Tropical Wailea Retreat!

Tropical Wailea Retreat!

1 bed 2 baths
PoolA/CWiFiBalcony
$230/night
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Oceanfront Elua Condo - Family Managed - 50 Steps to the Beachfront and Walk!

Oceanfront Elua Condo - Family Managed - 50 Steps to the Beachfront and Walk!

1 bed 1 bath
PoolA/CWiFiBalcony
$719/night
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Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wifi

Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wifi

1 bed 2 baths
PoolA/CWiFiBalcony
$278/night
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Grand Champions Villas 125, AC, King size Bed, close to Maui's best beaches!

Grand Champions Villas 125, AC, King size Bed, close to Maui's best beaches!

1 bed 2 baths
PoolA/CWiFiBalcony
$250/night
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Fantastically Remodeled Condo with Huge Ocean Views

Fantastically Remodeled Condo with Huge Ocean Views

1 bed 2 baths
PoolA/CWiFiBalcony
$321/night
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#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

1 bed 2 baths
PoolA/CWiFiBalcony
$277/night
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Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic

1 bed 1 bath
PoolA/CWiFiBalcony
$220/night
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July and August Fill in Special 249/nt Updated Designer Condo w/ Ocean Views

July and August Fill in Special 249/nt Updated Designer Condo w/ Ocean Views

1 bed 2 baths
PoolA/CWiFiBalcony
$277/night
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Wow !! What a Great View!!--GREAT REVIEWS !

Wow !! What a Great View!!--GREAT REVIEWS !

2 beds 2 baths
PoolA/CWiFiBalcony
$495/night
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The Perfect Location for a Relaxing Getaway

The Perfect Location for a Relaxing Getaway

1 bed 2 baths
PoolA/CWiFiBalcony
$253/night
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Kamaole Sands FRONT ROW OCEAN Building 10 unit 116

Kamaole Sands FRONT ROW OCEAN Building 10 unit 116

2 beds 2 baths
PoolA/CWiFiBalcony
$415/night
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Beautiful 1 bedroom condo. Private lanai overlooking fairway with ocean view!

Beautiful 1 bedroom condo. Private lanai overlooking fairway with ocean view!

1 bed 2 baths
PoolA/CWiFiBalcony
$213/night
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Wailea Elua 2101 - Your Getaway Amidst Beautiful Beachfront Grounds!

Wailea Elua 2101 - Your Getaway Amidst Beautiful Beachfront Grounds!

1 bed 2 baths
PoolA/CWiFiBalcony
$361/night
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Listen to the birds chirping!

Listen to the birds chirping!

1 bed 1 bath
PoolA/CWiFiBalcony
$185/night
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Ocean View Penthouse: Steps to Beach, Fast Wi-Fi

Ocean View Penthouse: Steps to Beach, Fast Wi-Fi

1 bed 1 bath
PoolA/CWiFiBalcony
$221/night
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NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA

NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA

2 beds 2 baths
PoolA/CWiFiBalcony
$517/night
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SPRING SALE $425 Ekahi 32c! Location! Designer Remodel. 2bdrm,2bth

SPRING SALE $425 Ekahi 32c! Location! Designer Remodel. 2bdrm,2bth

2 beds 2 baths
PoolA/CWiFiBalcony
$673/night
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Breathtaking Ocean Views, Luxury Penthouse, Right on Polo Beach, 2 Bed/2 Bath

Breathtaking Ocean Views, Luxury Penthouse, Right on Polo Beach, 2 Bed/2 Bath

2 beds 2 baths
PoolA/CWiFiBalcony
$1,205/night
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Beachfront, Polo Beach Wailea/Makena #103 - Accommodates 1-6, Free WiFi

Beachfront, Polo Beach Wailea/Makena #103 - Accommodates 1-6, Free WiFi

2 beds 2 baths
PoolA/CWiFiBalcony
$780/night
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Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View

Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View

2 beds 2 baths
PoolA/CWiFiBalcony
$744/night
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Experience the Magic of Maui at Ekahi 13C

Experience the Magic of Maui at Ekahi 13C

1 bed 2 baths
PoolA/CWiFiBalcony
$362/night
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Best Location @ Ekahi... year round sunsets from lanai, stroll to the Beach

Best Location @ Ekahi... year round sunsets from lanai, stroll to the Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$692/night
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Wailea Ekahi Village 30D

Wailea Ekahi Village 30D

1 bed 2 baths
PoolA/CWiFiBalcony
$406/night
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Lovely Remodelled Unit!

Lovely Remodelled Unit!

1 bed 2 baths
PoolA/CWiFiBalcony
$318/night
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Wailea Elua Village 1502

Wailea Elua Village 1502

2 beds 2 baths
PoolA/CWiFiBalcony
$621/night
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Wailea Ekahi 14F - Best Views! Walk to Keawakapu Beach. - Luxury in Paradise.

Wailea Ekahi 14F - Best Views! Walk to Keawakapu Beach. - Luxury in Paradise.

2 beds 2 baths
PoolA/CWiFiBalcony
$598/night
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Ekahi Lower Village Condo ~5B~

Ekahi Lower Village Condo ~5B~

1 bed 2 baths
PoolA/CWiFiBalcony
$401/night
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Wailea Ekahi Village 20H

Wailea Ekahi Village 20H

2 beds 2 baths
PoolA/CWiFiBalcony
$377/night
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Ekahi 6E - Great Location! Spacious, Views, Fantastic Vacation Condo!

Ekahi 6E - Great Location! Spacious, Views, Fantastic Vacation Condo!

1 bed 2 baths
PoolA/CWiFiBalcony
$296/night
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Wailea Ekahi Village 20J

Wailea Ekahi Village 20J

1 bed 2 baths
PoolA/CWiFiBalcony
$311/night
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Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

3 beds 2 baths
PoolA/CWiFiBalcony
$1,076/night
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Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

3 beds 3 baths
PoolA/CWiFiBalcony
$1,798/night
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Amazing Wailea Surf Villa: Luxury Condo - Owner Direct!

Amazing Wailea Surf Villa: Luxury Condo - Owner Direct!

2 beds 2 baths
PoolA/CWiFiBalcony
$1,180/night
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Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms

Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms

4 beds 3 baths
PoolA/CWiFiBalcony
$1,105/night
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Very Best Deluxe Ocean View...Panoramic View....First Class!!

Very Best Deluxe Ocean View...Panoramic View....First Class!!

3 beds 3 baths
PoolA/CWiFiBalcony
$881/night
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Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops

Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops

3 beds 3 baths
PoolA/CWiFiBalcony
$1,306/night
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Beautiful Palms at Wailea Condo!

Beautiful Palms at Wailea Condo!

1 bed 2 baths
PoolA/CWiFiBalcony
$305/night
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Fully Remodeled Modern Island Style!

Fully Remodeled Modern Island Style!

2 beds 2 baths
PoolA/CWiFiBalcony
$434/night
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The Best of 'The Palms' - Panoramic Views, Private End Unit #1102

The Best of 'The Palms' - Panoramic Views, Private End Unit #1102

2 beds 2 baths
PoolA/CWiFiBalcony
$396/night
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Just another day in Paradise!

Just another day in Paradise!

2 beds 2 baths
PoolA/CWiFiBalcony
$452/night
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Unit #1002 2 Bedroom 2 Bath Garden Deluxe

Unit #1002 2 Bedroom 2 Bath Garden Deluxe

2 beds 2 baths
PoolA/CWiFiBalcony
$1,003/night
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