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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
9–14 Aug
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4.96 out of 5 average rating, 200 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds
27 Aug – 1 Sept
4.94 out of 5 average rating, 330 reviews
Top guest favourite
Home in Kihei
South Maui Guesthouse
2 bedrooms, 2 queen beds
17–22 Aug
4.97 out of 5 average rating, 313 reviews
Guest favourite
Flat in Wailea
Wailea Oceanfront Luxury Front Row Escape
2 bedrooms, 3 beds
7–12 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Wailuku
Oceanfront Maalaea Harbor Condo with pool
2 bedrooms, 3 beds
31 Oct – 5 Nov
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms, 3 beds
8–13 Aug
4.98 out of 5 average rating, 140 reviews
Top guest favourite
Apartment in Kihei
Exceptional Ocean View - King Bed - Ocean Front!
2 bedrooms, 2 king beds
1–6 Sept
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: Big Blue Pacific
2 bedrooms, 3 beds
26–31 Aug
4.96 out of 5 average rating, 182 reviews
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds
3–8 Sept
4.99 out of 5 average rating, 142 reviews
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds
8–13 Aug
4.93 out of 5 average rating, 101 reviews
Guest favourite
Apartment in Wailea
Beach Front Wailea, Full Ocean View A/C, ELUA102
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Kihei
Chic Coastal Living in the Heart of Wailea
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Apartment in Wailea
Best Location, Panoramic Ocean View Remodel WE1508
2 bedrooms, 3 beds
2–7 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Kihei
Luxurious Wailea Ocean Vistas
1 bedroom, 2 beds
7–12 Aug
4.98 out of 5 average rating, 106 reviews
Top guest favourite
Townhouse in Wailea
Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
2 bedrooms, 4 beds
20–25 Aug
4.97 out of 5 average rating, 144 reviews
Superhost
Apartment in Wailea
A bit of paradise - Ocean Views Villa 1 bedroom
1 bedroom, 2 beds
7–12 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Kihei
Whale Watch From Your Lanai
2 bedrooms, 2 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
2 bedrooms, 4 beds
19–24 Aug
4.9 out of 5 average rating, 357 reviews
Guest favourite
Apartment in Kihei
Your Maui Luxury Escape - Wailea Beach Villas K107
2 bedrooms, 4 beds
28 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews