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

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Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Nov
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4.94 out of 5 average rating, 335 reviews
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Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Waterfall
2 bedrooms, 3 beds, 2 bathrooms
20–25 Oct
4.94 out of 5 average rating, 267 reviews
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Top guest favourite
Apartment in Kihei
Groovy bright condo 2 bed / 2 bath South Kihei
2 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
4.93 out of 5 average rating, 206 reviews
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Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
9–14 Nov
4.99 out of 5 average rating, 144 reviews
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Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
3 bedrooms, 6 beds, 2 bathrooms
8–13 Dec
4.98 out of 5 average rating, 52 reviews
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Top guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4 bedrooms, 4 beds, 3 bathrooms
29 Nov – 4 Dec
4.98 out of 5 average rating, 61 reviews
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Luxe
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
3–8 Nov
4.99 out of 5 average rating, 154 reviews
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Top guest favourite
Flat in Wailea
A.R.A Retreats: Ocean Breeze
2 bedrooms, 3 beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 53 reviews
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Guest favourite
Apartment in Wailea
Tropical Escape to Wailea with Stunning Oceanview
1 bedroom, 2 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 50 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 Kihei
Refined Resort Wailea Oceanview Vistas
2 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
4.97 out of 5 average rating, 38 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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Guest favourite
Flat in Wailea
Newly Remodeled-Quiet Location-Well Equipped-AC
3 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Flat in Wailea
A.R.A Retreats: The Grand Pacific
2 bedrooms, 4 beds, 2.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 33 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, 685 reviews
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Top guest favourite
Apartment in Wailea
Grand Champions Villas in Wailea, Maui
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Kihei
Last Minute Deal! Modern Across Best Beach NEW AC!
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 68 reviews
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Guest favourite
Apartment in Wailea
Oceanfront corner unit w/ sunset lanai
1 bedroom, 1 king bed, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 98 reviews