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

Guest favourite
Apartment in Wailea
Feel the Aloha at a Luxe Beach Chic Retreat
2 bedrooms, 3 beds, 2 private bathrooms
1–6 Aug
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4.97 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Aug
4.94 out of 5 average rating, 329 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Waterfall
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 262 reviews
Superhost
Apartment in Wailea
Wailea Elua | Steps to Ulua Beach, Ocean Views
2 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
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, 203 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
Superhost
Apartment in Wailea
A bit of paradise - Ocean Views Villa 1 bedroom
1 bedroom, 2 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Wailea
Wailea Surf Shack: Beaches, Shops & Golf!
1 bedroom, 2 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 138 reviews
Top guest favourite
Townhouse in Wailea
Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
2 bedrooms, 4 beds, 3 bathrooms
20–25 Aug
4.97 out of 5 average rating, 143 reviews
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
7–12 Aug
Top guest favourite
Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
2 bedrooms, 3 beds, 2 bathrooms
7–12 Aug
4.98 out of 5 average rating, 139 reviews
Top guest favourite
Apartment in Wailea
Maui Oasis Retreat At The Grand Champions #53
1 bedroom, 2 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Wailea
Amazing location! Chic Maui Getaway (ground floor)
1 bedroom, 2 beds, 2 bathrooms
7–12 Aug
4.98 out of 5 average rating, 57 reviews
Guest favourite
Apartment in Wailea
Gorgeous Condo in Wailea Ekahi Village!
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 80 reviews
Superhost
Apartment in Kihei
3BR Luxury Villa w/ AC Superb Views - HLR 23-3
3 bedrooms, 3 king beds, 3.5 bathrooms
8–13 Aug
Luxe
Apartment in Kihei
Wailea Ekolu – Oceanview in the Heart of Wailea
1 bedroom, 2 beds, 2 bathrooms
3–8 Aug
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Apartment in Kihei
Exceptional Ocean View - King Bed - Ocean Front!
2 bedrooms, 2 king beds, 2 bathrooms
6–11 Aug
4.96 out of 5 average rating, 50 reviews
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
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 69 reviews