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

Top guest favourite
Apartment in Wailea
Wailea Ekolu Village 2/2 with stunning ocean view!
2 bedrooms, 4 beds, 2 private bathrooms
5–10 Sept
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4.94 out of 5 average rating, 195 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
4.94 out of 5 average rating, 329 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Townhouse in Wailea
Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
4.97 out of 5 average rating, 143 reviews, 2 bedrooms, 4 beds, 3 bathrooms
20–25 Aug
Guest favourite
Apartment in Wailea
Gorgeous Condo in Wailea Ekahi Village!
4.94 out of 5 average rating, 80 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
4.94 out of 5 average rating, 64 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
4.9 out of 5 average rating, 357 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
11–16 Aug
Luxe
Apartment in Kihei
Wailea Ekolu – Oceanview in the Heart of Wailea
4.98 out of 5 average rating, 64 reviews, 1 bedroom, 2 beds, 2 bathrooms
3–8 Aug
Luxe
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
4.94 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Flat in Kihei
Maui Hill 2BR | Ocean View, Pool & King Beds
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Superhost
Apartment in Kihei
Luxury Oceanfront Condo by Maui's Best Beaches
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Guest favourite
Apartment in Wailea
Beach Front Wailea, Full Ocean View A/C, ELUA102
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
4.99 out of 5 average rating, 149 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
Superhost
Apartment in Wailea
A bit of paradise - Ocean Views Villa 1 bedroom
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Apartment in Wailea
A.R.A Retreats: Big Blue Pacific
4.96 out of 5 average rating, 181 reviews, 2 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
Top guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
4.96 out of 5 average rating, 69 reviews, 1 bedroom, 2 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
4.93 out of 5 average rating, 101 reviews, 3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
Top guest favourite
Home in Kihei
South Maui Guesthouse
4.97 out of 5 average rating, 311 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
Guest favourite
Apartment in Wailea
21B Grand Champions Studio -Ulua & Mokapu beaches
4.87 out of 5 average rating, 67 reviews, 1 bed, 1 bathroom
1–6 Aug