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

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Top guest favourite
Apartment in Wailea
A.R.A Retreats: Big Blue Pacific
2 bedrooms, 3 beds, 2 private bathrooms
11–16 Oct
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4.96 out of 5 average rating, 185 reviews
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Top guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
4–9 Nov
4.96 out of 5 average rating, 682 reviews
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Top guest favourite
Villa in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
3 bedrooms, 5 beds, 3.5 bathrooms
2–7 Dec
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Flat in Wailea
Great Location! Chic Wailea Getaway (1st floor)
1 bedroom, 2 beds, 2 bathrooms
19–24 Sept
4.98 out of 5 average rating, 60 reviews
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Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds, 3 bathrooms
17–22 Oct
4.93 out of 5 average rating, 104 reviews
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Top guest favourite
Apartment in Kihei
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
2 bedrooms, 3 beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 87 reviews
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Top guest favourite
Apartment in Kihei
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
2 bedrooms, 3 beds, 2 bathrooms
24–29 Nov
4.99 out of 5 average rating, 232 reviews
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Guest favourite
Apartment in Wailea
Best Location, Panoramic Ocean View Remodel WE1508
2 bedrooms, 3 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Apartment in Wailea
Wailea Ekolu Village 2/2 with stunning ocean view!
2 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
4.94 out of 5 average rating, 199 reviews
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Superhost
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms, 4 beds, 2 bathrooms
17–22 Oct
4.98 out of 5 average rating, 144 reviews
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Guest favourite
Flat in Wailea
Fabulous Ocean Views - Luxury 2br/2ba Penthouse
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Apartment in Wailea
Ocean/Golf Course Views, Tropical Resort in Wailea
1 bedroom, 2 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 209 reviews
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Top guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 70 reviews
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Top guest favourite
Home in Kihei
South Maui Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Oct
4.97 out of 5 average rating, 316 reviews
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Top guest favourite
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Apartment in Wailea
Palms 902 - Private Luxury Partial Ocean View
1 bedroom, 2 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Apartment in Wailea
Wailea Gem-Remodeled Ocean View
1 bedroom, 2 beds, 2 bathrooms
8–13 Oct
4.96 out of 5 average rating, 202 reviews