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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
15–20 Aug
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4.96 out of 5 average rating, 668 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Curved Slab
2 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
4.95 out of 5 average rating, 351 reviews
Top guest favourite
Apartment in Wailea
Luxury Vacation at Special Summer 2026 Rates
1 bedroom, 2 beds, 2 bathrooms
1–6 Jul
4.96 out of 5 average rating, 69 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, 141 reviews
Top guest favourite
Apartment in Wailea
*Fully Remodeled* Modern Island Style*
2 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
4.99 out of 5 average rating, 146 reviews
Top guest favourite
Apartment in Wailea
A.R.A Retreats: The Molokini
2 bedrooms, 2 king beds, 2 bathrooms
17–22 Jul
4.94 out of 5 average rating, 325 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, 90 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, 100 reviews
Top guest favourite
Apartment in Wailea
Maui Oasis Retreat At The Grand Champions #53
1 bedroom, 1 king bed, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Apartment in Wailea
Luxurious Tropical Retreat with Oceanview
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 43 reviews
Superhost
Apartment in Wailea
Beachfront 2BR condo w/ pool and ocean views
2 bedrooms, 2 bathrooms
3–8 Jul
Top guest favourite
Apartment in Kihei
Wailea Hidden Gem
1 bedroom, 2 beds, 2 bathrooms
4–9 Jul
4.94 out of 5 average rating, 81 reviews
Superhost
Flat in Wailea
Ocean View w/AC - Wailea Elua 306
2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Wailea
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
1 bedroom, 1 king bed, 1 bathroom
4–9 Jul
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Apartment in Kihei
Refined Resort Wailea Oceanview Vistas
2 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Kihei
Short Walk Keawakapu Beach*Full Remodel Oceanview
2 bedrooms, 2 beds, 1 bathroom
7–12 Jul
4.94 out of 5 average rating, 125 reviews
Top guest favourite
Apartment in Wailea
Ocean View! Pool! Ho'okipa @ Wailea Ekolu Village!
1 bedroom, 1 king bed, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 71 reviews
Guest favourite
Flat in Kihei
Chic Coastal Living in the Heart of Wailea
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Kihei
Romantic, Luxury Retreat - Couples Only
1 bedroom, 1 king bed, 2 bathrooms
2–7 Jul
4.98 out of 5 average rating, 233 reviews