Cottage holiday rentals in Wailea, Wailea-Makena
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Top-rated cottage rentals in Wailea, Wailea-Makena
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Wailea, Wailea-Makena cottage rentals
Cottage rentals with a hot tub
Cottage in Haiku-Pauwela
5.0 out of 5 average rating, 8 reviewsPrivacy, Luxury, Ocean View Cottage, HotTub, K-Bed
10 – 17 Apr
Cottage in Wailuku
5.0 out of 5 average rating, 7 reviewsRomantic and Private Cottage and Gazebo for two!
9 – 16 Aug
Cottage in Makawao
4.99 out of 5 average rating, 159 reviewsLuxury Upcountry retreat with breathtaking views!
20 – 27 Dec
Cottage in Kihei
4.98 out of 5 average rating, 220 reviewsLuxury Cottage, Saltwater Spa, Walk to Beach/Dining/Shops
26 Feb – 5 Mar
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 75 reviewsLeilani's "Leimomi" Cottage - County Licensed
21 – 28 Sept
Cottage in Kihei
4.82 out of 5 average rating, 68 reviewsTropical Getaway: Maui's Best - Honeymoon Suite
23 – 30 Sept
Cottage in Haiku-Pauwela
4.79 out of 5 average rating, 174 reviewsHawaiian DreamTemple- Tropical Oasis BBPH20120004
14 – 21 Jan
Private cottage rentals
Cottage in Haiku-Pauwela
5.0 out of 5 average rating, 68 reviewsHaiku Hideaway - Stand-alone 2 bedroom farm house
15 – 22 July
Cottage in Lahaina
4.94 out of 5 average rating, 66 reviewsCharming Kaanapali cottage with ocean view
12 – 19 Oct
Cottage in Paia
4.72 out of 5 average rating, 18 reviewsWalk to small beach, charming cottage
18 – 25 Nov
Cottage in Lahaina
4.8 out of 5 average rating, 40 reviewsKaanapali Cottage ICC24 ocean view- House for rent
30 Sept – 7 Oct
Cottage in Paia
4.84 out of 5 average rating, 80 reviewsCharming Plantation Style Cottage in Kuau
3 – 10 Apr
Cottage in Kihei
5.0 out of 5 average rating, 44 reviewsBeautiful Beach Cottage: lush garden paradise
1 – 8 July
Cottage in Kihei
4.91 out of 5 average rating, 22 reviewsRemodeled 2BR | Deck | Washer/Dryer
12 – 19 Feb
Cottage in Maui County
4.94 out of 5 average rating, 67 reviewsOcean View Cottage. Island Retreat.
25 Sept – 2 Oct
Luxury cottage rentals
Cottage in Lahaina
4.58 out of 5 average rating, 76 reviewsPrivate Hawaiian Cottage Gem 3/2 🌺 Stellar Lanai
10 – 17 Sept
Cottage in Paia
4.72 out of 5 average rating, 205 reviewsLani Paradise Oceanfront Cottage
14 – 21 July
Cottage in Lahaina
4.71 out of 5 average rating, 56 reviewsPono Plantation Maui-'Summer In Paradise-3 Bedroom
1 – 8 Mar
Cottage in Haiku-Pauwela
4.79 out of 5 average rating, 174 reviewsHawaiian DreamTemple- Tropical Oasis BBPH20120004
14 – 21 Jan
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