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

Guest favourite
Apartment in Wailea
Feel the Aloha at a Luxe Beach Chic Retreat
2 bedrooms, 3 beds, 2 private bathrooms
28 Aug – 2 Sept
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4.97 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
4.94 out of 5 average rating, 330 reviews
Top guest favourite
Apartment in Wailea
Maui Oasis Retreat At The Grand Champions #53
1 bedroom, 2 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Apartment in Wailea
Ocean/Golf Course Views, Tropical Resort in Wailea
1 bedroom, 2 beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 206 reviews
Superhost
Apartment in Wailea
Wailea Elua | Steps to Ulua Beach, Ocean Views
2 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
Guest favourite
Flat in Kihei
Luxurious Wailea Ocean Vistas
1 bedroom, 2 beds, 2 bathrooms
7–12 Aug
4.98 out of 5 average rating, 106 reviews
Top guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 676 reviews
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms, 4 beds, 2.5 bathrooms
19–24 Aug
4.9 out of 5 average rating, 357 reviews
Superhost
Apartment in Wailea
Polo Beach Club 409 | Ocean View, Pool + Hot Tub
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Kihei
South Maui Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 313 reviews
Top guest favourite
Flat in Kihei
Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub
1 bedroom, 2 beds, 2 bathrooms
18–23 Oct
4.92 out of 5 average rating, 13 reviews
Guest favourite
Flat in Wailea
Fabulous Ocean Views - Luxury 2br/2ba Penthouse
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
7–12 Aug
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Apartment in Kihei
Romantic, Luxury Retreat w/Ocean View-Couples Only
1 bedroom, 1 king bed, 2 bathrooms
12–17 Oct
4.99 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Wailea
Wailea Escape/Golf Views, Beaches & Family Comfort
2 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 27 reviews
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
8–13 Aug
Apartment in Wailea
New! Rare 3 BR Wailea Condo-Beaches, Shops & Golf
3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
New place to stay
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
3–8 Sept
4.99 out of 5 average rating, 142 reviews
Guest favourite
Apartment in Wailea
Best Location, Panoramic Ocean View Remodel WE1508
2 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 17 reviews