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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, 329 reviews
Top guest favourite
Apartment in Kihei
Wailea Hidden Gem
4.94 out of 5 average rating, 82 reviews, 1 bedroom, 2 beds, 2 bathrooms
21–26 Jul
Guest favourite
Apartment in Wailea
A.R.A Retreats: The Townhouse
4.9 out of 5 average rating, 355 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Apartment in Kihei
Ekahi 22C Toes in the Sand in Under 2 Minutes
4.95 out of 5 average rating, 99 reviews, 2 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Apartment in Wailea
Boathouse Studio Condo in Wailea, Hawaii
4.98 out of 5 average rating, 476 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Jul – 3 Aug
Superhost
Apartment in Kihei
Wailea Ekahi 12A | Ocean Views & Walk-Out Patio
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
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
Guest favourite
Flat in Kihei
Luxe Wailea Getaway | Stunning Ocean Views
4.84 out of 5 average rating, 19 reviews, 1 bedroom, 1 bed, 2 bathrooms
7–12 Aug
Superhost
Flat in Wailea
* Wailea Elua 806 *
3 bedrooms, 3 beds, 2 bathrooms
28 Jul – 2 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
Top guest favourite
Apartment in Kihei
Wailea Ekahi Getaway•Walk to Keawakapu beach
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Jul
Luxe
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
12–17 Aug
Guest favourite
Flat in Wailea
Spacious 3BR/2BA Condo in Wailea
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
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
5–10 Aug
Top guest favourite
Guest suite in Kihei
Sweeping Panoramic Ocean Views - Private Ohana
4.99 out of 5 average rating, 142 reviews, 2 bedrooms, 2 beds, 2 bathrooms
3–8 Sept
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
29 Aug – 3 Sept
Top guest favourite
Flat in Kihei
Go Golfing from a Peaceful Apartment in a Beach Community
4.88 out of 5 average rating, 168 reviews, 2 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
Top guest favourite
Apartment in Kihei
Island Style Beautiful Home - the Palms at Wailea
4.97 out of 5 average rating, 59 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Luxe
Apartment in Kihei
Wailea Ekolu – Oceanview in the Heart of Wailea
4.98 out of 5 average rating, 61 reviews, 1 bedroom, 2 beds, 2 bathrooms
27 Jul – 1 Aug