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

Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 3 beds, 2 private bathrooms
27 Aug – 1 Sept
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4.94 out of 5 average rating, 331 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
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
Luxurious Tropical Retreat with Oceanview
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 45 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
Home in Kihei
South Maui Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 314 reviews
Guest favourite
Flat in Wailea
Wailea Oceanfront Luxury Front Row Escape
2 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Kihei
Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub
1 bedroom, 2 beds, 2 bathrooms
22–27 Oct
4.92 out of 5 average rating, 13 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
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 676 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 Kihei
Spacious 3bd on Golf Course I Grand Champions 105
3 bedrooms, 3 beds, 2 bathrooms
13–18 Aug
4.93 out of 5 average rating, 124 reviews
Top guest favourite
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
1 bedroom, 1 king bed, 1 bathroom
21–26 Aug
4.94 out of 5 average rating, 66 reviews
Superhost
Apartment in Kihei
Whale Watch From Your Lanai
2 bedrooms, 2 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Apartment in Wailea
Wailea Elua 1103 | Oceanview, 1-min to Beach
2 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Wailea
Wailea Elua 2401 | Wrap-Around Lanai & Ocean View
1 bedroom, 2 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
12–17 Aug
4.96 out of 5 average rating, 70 reviews
Guest favourite
Apartment in Kihei
Upscale and Elegant Vistas
1 bedroom, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 128 reviews