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

Top guest favourite
Apartment in Wailea
Gorgeous 2 Story Townhouse in Wailea w/ Ocean View
2 bedrooms, 4 beds, 3 private bathrooms
2–7 Aug
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4.94 out of 5 average rating, 181 reviews
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 142 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
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
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
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
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
Apartment in Wailea
A bit of paradise - Ocean Views Villa 1 bedroom
1 bedroom, 2 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 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
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
Guest favourite
Apartment in Wailea
Gorgeous Condo in Wailea Ekahi Village!
1 bedroom, 2 beds, 1 bathroom
24–29 Jul
4.94 out of 5 average rating, 77 reviews
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
Guest favourite
Apartment in Wailea
Beach Front Wailea, Full Ocean View A/C, ELUA102
2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
5.0 out of 5 average rating, 9 reviews
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, 138 reviews
Top guest favourite
Flat in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 10 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
Wailea Resort studio suite
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 671 reviews
Apartment in Kihei
Tropical Escape with Endless Coastal Views
1 bedroom, 2 beds, 2 bathrooms
21–26 Jul
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Kihei
South Maui Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Aug
4.97 out of 5 average rating, 309 reviews