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

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Guest favourite
Apartment in Wailea
Tropical Escape to Wailea with Stunning Oceanview
1 bedroom, 2 beds, 1 private bathroom
10–15 Oct
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4.98 out of 5 average rating, 50 reviews
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Top guest favourite
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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Top guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
4–9 Nov
4.96 out of 5 average rating, 685 reviews
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Top guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms, 4 beds, 3 bathrooms
29 Nov – 4 Dec
4.98 out of 5 average rating, 61 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, 52 reviews
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Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Nov
4.94 out of 5 average rating, 335 reviews
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Top guest favourite
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, 364 reviews
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Top guest favourite
Apartment in Kihei
Your Maui Luxury Escape - Wailea Beach Villas K107
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Wailea
Fabulous Ocean Views - Luxury 2br/2ba Penthouse
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
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, 145 reviews
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Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 27 reviews
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Superhost
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 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
19–24 Oct
4.94 out of 5 average rating, 127 reviews
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Top guest favourite
Flat in Wailea
A.R.A Retreats: The Grand Pacific
2 bedrooms, 4 beds, 2.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Apartment in Kihei
*Last Minute Deal*Luxurious*2b/2b OceanView Wailea
2 bedrooms, 2 king beds, 2 bathrooms
7–12 Dec
4.89 out of 5 average rating, 148 reviews
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Top guest favourite
Apartment in Wailea
Wailea Surf Shack: Beaches, Shops & Golf!
1 bedroom, 2 beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 146 reviews
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Luxe
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
3–8 Nov
4.99 out of 5 average rating, 154 reviews
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Superhost
Home in Kihei
Ocean View 21-6
3 bedrooms, 4 beds, 3.5 bathrooms
17–22 Nov
5.0 out of 5 average rating, 4 reviews
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Flat in Kihei
The Best Condo in Wailea Ekahi Village!
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
5.0 out of 5 average rating, 3 reviews