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

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Top guest favourite
Apartment in Wailea
Large 1BR, Palms at Wailea, Pool, Walk to Beach
1 bedroom, 2 beds, 2 private bathrooms
11–16 Oct
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4.97 out of 5 average rating, 116 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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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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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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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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Apartment in Wailea
Best Location, Panoramic Ocean View Remodel WE1508
2 bedrooms, 3 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 17 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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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
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
2 bedrooms, 3 beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 87 reviews
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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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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
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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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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, 144 reviews
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Apartment in Kihei
Wailea Ekolu I Remodeled Ocean-View Retreat
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
New place to stay
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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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Apartment in Kihei
PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
2 bedrooms, 3 beds, 2 bathrooms
9–14 Oct
4.99 out of 5 average rating, 83 reviews
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Flat in Kihei
Go Golfing from a Peaceful Apartment in a Beach Community
2 bedrooms, 3 beds, 2 bathrooms
21–26 Oct
4.88 out of 5 average rating, 173 reviews
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Apartment in Wailea
Oceanfront corner unit w/ sunset lanai
1 bedroom, 1 king bed, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 20 reviews
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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