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

Guest favourite
Apartment in Wailea
Wailea Gem-Remodeled Ocean View
1 bedroom, 2 beds, 2 private bathrooms
8–13 Oct
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4.96 out of 5 average rating, 202 reviews
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, 86 reviews
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Apartment in Kihei
Wailea Hidden Gem
1 bedroom, 2 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 86 reviews
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Apartment in Kihei
Refined Resort Wailea Oceanview Vistas
2 bedrooms, 3 beds, 2 bathrooms
23–28 Sept
4.97 out of 5 average rating, 37 reviews
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Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.95 out of 5 average rating, 362 reviews
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Apartment in Kihei
Romantic, Luxury Retreat w/Ocean View-Couples Only
1 bedroom, 1 king bed, 2 bathrooms
25–30 Apr
4.99 out of 5 average rating, 197 reviews
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Flat in Kihei
Luxurious Wailea Ocean Vistas
1 bedroom, 2 beds, 2 bathrooms
3–8 Oct
4.98 out of 5 average rating, 108 reviews
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Apartment in Kihei
Your Maui Luxury Escape - Wailea Beach Villas K107
2 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 14 reviews
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Apartment in Kihei
Luxury condo w/THE BEST view & location on Maui!
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 57 reviews
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Villa in Kihei
HO'OLEI DESIGNER VILLA24-4 AC WIFI BEACH POOL WALK
3 bedrooms, 3 king beds, 3.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 127 reviews
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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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, 33 reviews
Guest favourite
Apartment in Kihei
Wailea Elua Village 803, Ocean Views, Modern Reno
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Wailea
Gorgeous Condo in Wailea Ekahi Village!
1 bedroom, 2 beds, 1 bathroom
30 Nov – 5 Dec
4.94 out of 5 average rating, 85 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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Flat in Wailea
Wailea Escape/Golf Views, Beaches & Family Comfort
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Apartment in Kihei
Luxury Condo in Wailea Ekahi w/Direct Beach Access
1 bedroom, 2 beds, 2 bathrooms
1–6 Oct
4.91 out of 5 average rating, 119 reviews
Guest favourite
Apartment in Kihei
2BD Breathtaking Ocean Views -Wailea Ekolu 907
2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Apartment in Wailea
Wailea Elua 1504 | Panoramic Ocean Views
2 bedrooms, 3 beds, 2 bathrooms
8–13 Oct
5.0 out of 5 average rating, 13 reviews