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

Top guest favourite
Apartment in Wailea
Grand Champions 169 Beautiful 3 BR on the Fairway!
3 bedrooms, 4 beds, 2 private bathrooms
22–27 Aug
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4.98 out of 5 average rating, 189 reviews
Flat in Kihei
Brand-New Interior | 5-Min Walk to Beach | 2 Baths
New place to stay, 1 bedroom, 2 beds, 2 bathrooms
8–13 Jul
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
4.94 out of 5 average rating, 327 reviews, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
4.95 out of 5 average rating, 354 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
4.99 out of 5 average rating, 147 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Apartment in Wailea
Maui Oasis Retreat At The Grand Champions #53
5.0 out of 5 average rating, 74 reviews, 1 bedroom, 1 bed, 2 bathrooms
22–27 Jul
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
4.99 out of 5 average rating, 142 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
Superhost
Flat in Wailea
Ocean View w/AC - Wailea Elua 306
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Apartment in Wailea
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
4.94 out of 5 average rating, 62 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Apartment in Kihei
Tropical Escape with Endless Coastal Views
4.95 out of 5 average rating, 42 reviews, 1 bedroom, 2 beds, 2 bathrooms
9–14 Jul
Superhost
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
3–8 Jul
Top guest favourite
Apartment in Wailea
Wailea Surf Shack: Golf, shopping & beaches!
5.0 out of 5 average rating, 134 reviews, 1 bedroom, 2 beds, 2 bathrooms
10–15 Jul
Guest favourite
Apartment in Wailea
Tropical Escape to Wailea with Stunning Oceanview
4.98 out of 5 average rating, 43 reviews, 1 bedroom, 2 beds, 1 bathroom
23–28 Oct
Top guest favourite
Flat in Kihei
Luxurious Wailea Ocean Vistas
5.0 out of 5 average rating, 101 reviews, 1 bedroom, 2 beds, 2 bathrooms
13–18 Jul
Flat in Wailea
Grand Champions 067
1 bedroom, 2 beds, 2 bathrooms
10–15 Jul
Superhost
Home in Wailea
Wailea Elua Village 1603
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Superhost
Apartment in Kihei
Wailea Ekahi 12A | Ocean Views & Walk-Out Patio
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
Top guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
5.0 out of 5 average rating, 43 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 Oct
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
5.0 out of 5 average rating, 40 reviews, 3 bedrooms, 6 beds, 2 bathrooms
25–30 Oct