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

Superhost
Apartment in Wailea
Romantic One BR Condo (Remodeled)
1 bedroom, 1 bed, 1 bathroom
5–10 Aug
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4.84 out of 5 average rating, 198 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
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 675 reviews
Guest favourite
Flat in Wailea
Wailea Oceanfront Luxury Front Row Escape
2 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 5 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, 205 reviews
Superhost
Apartment in Wailea
Wailea Elua | Steps to Ulua Beach, Ocean Views
2 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
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
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
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
Top guest favourite
Townhouse in Kihei
Maui Resort Walk to Beach w/King, Pool, 2 Hot Tubs
1 bedroom, 2 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Apartment in Kihei
Exceptional Ocean View - King Bed - Ocean Front!
2 bedrooms, 2 king beds, 2 bathrooms
6–11 Aug
4.96 out of 5 average rating, 51 reviews
Superhost
Apartment in Kihei
Whale Watch From Your Lanai
2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Wailea
Beach Front Wailea, Full Ocean View A/C, ELUA102
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Kihei
Brand-New Interior | 5-Min Walk to Beach | 2 Baths
1 bedroom, 2 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 10 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
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 65 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
Top guest favourite
Apartment in Wailea
A.R.A retreats: The OG
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
4.91 out of 5 average rating, 351 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