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

Top guest favourite
Apartment in Wailea
Wailea Resort studio suite
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
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4.96 out of 5 average rating, 671 reviews
Guest favourite
Flat in Wailea
A.R.A Retreats: Birds Eye View
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Apartment in Wailea
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.94 out of 5 average rating, 62 reviews
Top guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
4.93 out of 5 average rating, 100 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.95 out of 5 average rating, 355 reviews
Top guest favourite
Apartment in Kihei
Luxe 2bed Wailea, 5-min walk to beach, ocean view,
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Wailea
The BEST Condo in Wailea: Elua Resort 1002
2 bedrooms, 2 king beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Apartment in Wailea
Modern Renovated Palms at Wailea Condo!
1 bedroom, 2 beds, 2 bathrooms
26–31 Jul
4.97 out of 5 average rating, 109 reviews
Home in Wailea
The Butterfly Home Maui
4 bedrooms, 5 beds, 3.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Wailea
Fabulous Ocean Views- Luxury 2 Bed 2 Bath
2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Kihei
Luxurious Wailea Ocean Vistas
1 bedroom, 2 beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 103 reviews
Top guest favourite
Apartment in Wailea
Boathouse Studio Condo in Wailea, Hawaii
1 bedroom, 1 queen bed, 1 bathroom
29 Jul – 3 Aug
4.98 out of 5 average rating, 476 reviews
Top guest favourite
Townhouse in Wailea
Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
2 bedrooms, 4 beds, 3 bathrooms
8–13 Jul
4.97 out of 5 average rating, 143 reviews
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
1 bedroom, 2 beds, 2 bathrooms
8–13 Jul
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Apartment in Wailea
Aloha Moon - The Honeymoon Hideaway
1 bedroom, 1 king bed, 1 bathroom
8–13 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Wailea
Amazing location! Chic Maui Getaway (ground floor)
1 bedroom, 2 beds, 2 bathrooms
8–13 Jul
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Apartment in Wailea
21A Grand Champions 1 Bed - Ulua & Mokapu beaches
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.93 out of 5 average rating, 92 reviews
Top guest favourite
Apartment in Kihei
Romantic, Luxury Retreat w/Ocean View-Couples Only
1 bedroom, 1 king bed, 2 bathrooms
28 Aug – 2 Sept
4.99 out of 5 average rating, 191 reviews