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Search results; Over 1,000 homes in Wailea, Wailea-Makena

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Guest favourite
Apartment in Wailea
Gorgeous Condo in Wailea Ekahi Village!
1 bedroom, 2 beds, 1 private bathroom
18–23 Oct
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4.94 out of 5 average rating, 84 reviews
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Apartment in Wailea
A.R.A Retreats: Big Blue Pacific
2 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 183 reviews
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Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 50 reviews
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Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
4.99 out of 5 average rating, 151 reviews
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Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
3–8 Sept
4.99 out of 5 average rating, 142 reviews
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Flat in Wailea
Spacious 3BR/2BA Condo in Wailea
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.92 out of 5 average rating, 13 reviews
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Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms, 4 beds, 2 bathrooms
17–22 Oct
4.98 out of 5 average rating, 142 reviews
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Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 61 reviews
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Apartment in Wailea
Best Location, Panoramic Ocean View Remodel WE1508
2 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 17 reviews
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Flat in Wailea
A.R.A Retreats: The Grand Pacific
2 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 32 reviews
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Apartment in Kihei
Romantic, Luxury Retreat w/Ocean View-Couples Only
1 bedroom, 1 king bed, 2 bathrooms
25–30 Apr
4.99 out of 5 average rating, 197 reviews
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Room in Kihei
Garden Room, private bathroom, separate entrance
1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 463 reviews
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Apartment in Kihei
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
2 bedrooms, 2 king beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 104 reviews
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Top guest favourite
Apartment in Kihei
Large 2 Bedroom 2 Bath Ground Unit Maui Parkshore
2 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
4.85 out of 5 average rating, 167 reviews
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Apartment in Kihei
Gorgeous Ocean View Condo steps to the beach
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 93 reviews
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Guest favourite
Apartment in Kihei
Maui Kamaole Kihei Resort I Beaches, Pools, Tennis
2 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 22 reviews
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Apartment in Kihei
Spacious 3bd on Golf Course I Grand Champions 105
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.93 out of 5 average rating, 125 reviews
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Apartment in Kihei
Beautifully Updated Oceanview Condo in Wailea
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
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Townhouse in Wailea
Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
2 bedrooms, 4 beds, 3 bathrooms
17–22 Sept
4.97 out of 5 average rating, 145 reviews