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

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Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
1 bedroom, 2 beds, 1 private bathroom
10–15 Oct
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4.94 out of 5 average rating, 95 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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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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Apartment in Wailea
A.R.A retreats: The OG
2 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.91 out of 5 average rating, 354 reviews
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Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 151 reviews
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Apartment in Wailea
21B Grand Champions Studio -Ulua & Mokapu beaches
1 king bed, 1 bathroom
5–10 Sept
4.87 out of 5 average rating, 69 reviews
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Apartment in Kihei
Groovy bright condo 2 bed / 2 bath South Kihei
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.93 out of 5 average rating, 204 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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Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds, 2 bathrooms
24–29 Nov
5.0 out of 5 average rating, 48 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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Top guest favourite
Apartment in Kihei
Peggy's Place - Best Beachfront Condo for Families
2 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.98 out of 5 average rating, 85 reviews
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Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
9–14 Sept
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Apartment in Kihei
Wailea Ekolu - Gorgeous Ocean View - AC, Smart TV!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.89 out of 5 average rating, 131 reviews
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Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Flat in Wailea
A.R.A Retreats: The Grand Pacific
2 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 32 reviews
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Apartment in Wailea
Comfortable Design with Ocean Views
3 bedrooms, 5 beds, 2 bathrooms
12–17 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
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Flat in Kihei
Grand Champions - Ocean & Golf View, King Bed, A/C
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 132 reviews
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Superhost
Apartment in Kihei
3BR Luxury Villa w/ AC Superb Views - HLR 23-3
3 bedrooms, 3 king beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews