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

Top guest favourite
Apartment in Wailea
Boathouse Studio Condo in Wailea, Hawaii
1 bedroom, 1 bed, 1 private bathroom
29 Jul – 3 Aug
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4.98 out of 5 average rating, 476 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
2–7 Aug
Top guest favourite
Apartment in Wailea
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
4.94 out of 5 average rating, 62 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
4.95 out of 5 average rating, 355 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Apartment in Kihei
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
5.0 out of 5 average rating, 81 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 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
8–13 Jul
Guest favourite
Apartment in Wailea
The BEST Condo in Wailea: Elua Resort 1002
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Jul
Guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
4.93 out of 5 average rating, 100 reviews, 3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
Top guest favourite
Apartment in Wailea
Modern Renovated Palms at Wailea Condo!
4.97 out of 5 average rating, 109 reviews, 1 bedroom, 2 beds, 2 bathrooms
26–31 Jul
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
10–15 Aug
Home in Wailea
The Butterfly Home Maui
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
26–31 Aug
Top guest favourite
Flat in Kihei
Luxurious Wailea Ocean Vistas
5.0 out of 5 average rating, 103 reviews, 1 bedroom, 2 beds, 2 bathrooms
13–18 Jul
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
13–18 Jul
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 Jul
Top guest favourite
Villa in Wailea
Luxury Oceanview Wailea Retreat with Sunset Views
5.0 out of 5 average rating, 40 reviews, 3 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
5.0 out of 5 average rating, 44 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 Oct
Guest favourite
Flat in Wailea
Fabulous Ocean Views- Luxury 2 Bed 2 Bath
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Apartment in Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
4.98 out of 5 average rating, 138 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 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
14–19 Jul