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

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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, 683 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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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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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, 363 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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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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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, 51 reviews
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Guest favourite
Townhouse in Kihei
Wailea villa w/ private elevator and pool
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Oct
4.95 out of 5 average rating, 59 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
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 53 reviews
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Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms, 4 beds, 2.5 bathrooms
16–21 Oct
4.9 out of 5 average rating, 358 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
Apartment in Wailea
Ocean/Golf Course Views, Tropical Resort in Wailea
1 bedroom, 2 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 208 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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Top guest favourite
Apartment in Wailea
Tropical Escape to Wailea with Stunning Oceanview
1 bedroom, 2 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 50 reviews
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Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds, 3 bathrooms
17–22 Oct
4.93 out of 5 average rating, 104 reviews
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Guest favourite
Apartment in Kihei
Wailea Ekolu 1204 - Modern, Ocean View, Split AC !
1 bedroom, 2 beds, 2 bathrooms
9–14 Oct
5.0 out of 5 average rating, 6 reviews