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

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Top guest favourite
Apartment in Wailea
Ocean/Golf Course Views, Tropical Resort in Wailea
1 bedroom, 2 beds, 2 private bathrooms
27 Oct – 1 Nov
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4.98 out of 5 average rating, 209 reviews
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Apartment in Wailea
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
4–9 Nov
4.96 out of 5 average rating, 682 reviews
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Villa in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
3 bedrooms, 5 beds, 3.5 bathrooms
2–7 Dec
5.0 out of 5 average rating, 16 reviews
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Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 53 reviews
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Apartment in Wailea
Large 1BR, Palms at Wailea, Pool, Walk to Beach
1 bedroom, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 115 reviews
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Top guest favourite
Apartment in Wailea
Wailea Surf Shack: Beaches, Shops & Golf!
1 bedroom, 2 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 145 reviews
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Top guest favourite
Villa in Kihei
HO'OLEI DESIGNER VILLA24-4 AC WIFI BEACH POOL WALK
3 bedrooms, 3 king beds, 3.5 bathrooms
26 Sept – 1 Oct
4.94 out of 5 average rating, 127 reviews
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Top guest favourite
Flat in Wailea
Great Location! Chic Wailea Getaway (1st floor)
1 bedroom, 2 beds, 2 bathrooms
19–24 Sept
4.98 out of 5 average rating, 60 reviews
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Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 363 reviews
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Guest favourite
Apartment in Wailea
Oceanfront corner unit w/ sunset lanai
1 bedroom, 1 king bed, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds, 2 bathrooms
8–13 Dec
4.98 out of 5 average rating, 50 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 Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 70 reviews
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Top guest favourite
Apartment in Kihei
Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
1 king bed, 1 bathroom
29 Sept – 4 Oct
4.99 out of 5 average rating, 135 reviews
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Top guest favourite
Apartment in Kihei
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 106 reviews
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Superhost
Apartment in Kihei
Top Floor Oceanfront 2BR on Po'olenalena Beach
2 bedrooms, 4 beds, 2 bathrooms
1–6 Dec
New place to stay
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Guest favourite
Townhouse in Kihei
Wailea Oceanviewvilla w/ ocean views
3 bedrooms, 4 beds, 3.5 bathrooms
26 Sept – 1 Oct
4.94 out of 5 average rating, 33 reviews
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Top guest favourite
Apartment in Wailea
Elua 1310 Oceanfront -Family Managed-Remodeled9/25
1 bedroom, 2 beds, 1 bathroom
30 Sept – 5 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
9–14 Nov
4.99 out of 5 average rating, 143 reviews