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

Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 3 beds, 2 private bathrooms
2–7 Aug
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4.94 out of 5 average rating, 327 reviews
Top guest favourite
Flat in Kihei
Barefoot Luxury at it's Finest | 3bd Villa | E-201
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Oct
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
Guest favourite
Flat in Wailea
A.R.A Retreats: Birds Eye View
4.97 out of 5 average rating, 101 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Kihei
Private S. Maui home w/ocean views, pool, hot tub
4.96 out of 5 average rating, 99 reviews, 3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
Guest favourite
Apartment in Wailea
Wailea Elua condo - Ocean Views | Gym | Pickleball
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 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
10–15 Aug
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
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 Kihei
Stunning Luxury Remodel I Wailea Beach Villas J206
4.98 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Aug
Top guest favourite
Apartment in Wailea
Grand Champions 169 Beautiful 3 BR on the Fairway!
4.98 out of 5 average rating, 190 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Guest favourite
Apartment in Kihei
Your Maui Luxury Escape - Wailea Beach Villas K107
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Apartment in Kihei
Wailea Beachfront Direct Ocean Views 4 Bd/3 Ba
4.98 out of 5 average rating, 60 reviews, 4 bedrooms, 4 beds, 3 bathrooms
28 Jul – 2 Aug
Guest favourite
Flat in Wailea
Wailea Ekahi 24C, Summer in Paradise in Style!
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 6 beds, 2 bathrooms
6–11 Jul
Guest favourite
Apartment in Kihei
3BR spacious Condo with Ocean View in top location
4.93 out of 5 average rating, 188 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Aug
Guest favourite
Apartment in Kihei
Keawakapu Beach luxury w/tropical garden view
4.92 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Apartment in Wailea
Boathouse Studio Condo in Wailea, Hawaii
4.98 out of 5 average rating, 475 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Jul – 3 Aug
Superhost
Flat in Wailea
Ocean View w/AC - Wailea Elua 306
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
Superhost
Apartment in Kihei
3BR Luxury Villa w/ AC Superb Views - HLR 23-3
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul