Cottage vacation rentals in Wailea, Wailea-Makena
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Wailea, Wailea-Makena
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
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
Apr 10 – 17
Cottage in Wailuku
5.0 out of 5 average rating, 7 reviewsRomantic and Private Cottage and Gazebo for two!
Aug 9 – 16
Cottage in Makawao
4.99 out of 5 average rating, 159 reviewsLuxury Upcountry retreat with breathtaking views!
Dec 20 – 27
Cottage in Kihei
4.98 out of 5 average rating, 220 reviewsLuxury Cottage, Saltwater Spa, Walk to Beach/Dining/Shops
Feb 26 – Mar 5
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 75 reviewsLeilani's "Leimomi" Cottage - County Licensed
Sep 21 – 28
Cottage in Kihei
4.82 out of 5 average rating, 68 reviewsTropical Getaway: Maui's Best - Honeymoon Suite
Sep 23 – 30
Cottage in Haiku-Pauwela
4.79 out of 5 average rating, 174 reviewsHawaiian DreamTemple- Tropical Oasis BBPH20120004
Jan 14 – 21
Private cottage rentals
Cottage in Haiku-Pauwela
5.0 out of 5 average rating, 68 reviewsHaiku Hideaway - Stand-alone 2 bedroom farm house
Jul 15 – 22
Cottage in Lahaina
4.94 out of 5 average rating, 66 reviewsCharming Kaanapali cottage with ocean view
Oct 12 – 19
Cottage in Paia
4.72 out of 5 average rating, 18 reviewsWalk to small beach, charming cottage
Nov 18 – 25
Cottage in Lahaina
4.8 out of 5 average rating, 40 reviewsKaanapali Cottage ICC24 ocean view- House for rent
Sep 30 – Oct 7
Cottage in Paia
4.84 out of 5 average rating, 80 reviewsCharming Plantation Style Cottage in Kuau
Apr 3 – 10
Cottage in Kihei
5.0 out of 5 average rating, 44 reviewsBeautiful Beach Cottage: lush garden paradise
Jul 1 – 8
Cottage in Maui County
4.94 out of 5 average rating, 67 reviewsOcean View Cottage. Island Retreat.
Sep 25 – Oct 2
Cottage in Kihei
4.91 out of 5 average rating, 22 reviewsRemodeled 2BR | Deck | Washer/Dryer
Feb 12 – 19
Luxury cottage rentals
Cottage in Lahaina
4.58 out of 5 average rating, 76 reviewsPrivate Hawaiian Cottage Gem 3/2 🌺 Stellar Lanai
Sep 10 – 17
Cottage in Paia
4.72 out of 5 average rating, 205 reviewsLani Paradise Oceanfront Cottage
Jul 14 – 21
Cottage in Lahaina
4.71 out of 5 average rating, 56 reviewsPono Plantation Maui-'Summer In Paradise-3 Bedroom
Mar 1 – 8
Cottage in Haiku-Pauwela
4.79 out of 5 average rating, 174 reviewsHawaiian DreamTemple- Tropical Oasis BBPH20120004
Jan 14 – 21
Destinations to explore
- Cottage rentals Hawaii
- Cottage rentals Hawaii
- Cottage rentals Maui
- Cottage rentals Maui County
- Family-friendly rentals Wailea
- House rentals Wailea
- Rentals with a washer and dryer Wailea
- Pet-friendly rentals Wailea
- Rentals with beach access Wailea
- Rentals with pools Wailea
- Rentals with an EV charger Wailea
- Rentals with outdoor seating Wailea
- Beach house rentals Wailea
- Rentals with a hot tub Wailea
- Kid-friendly rentals Wailea
- Apartment rentals Wailea
- Beachfront rentals Wailea
- Fitness-friendly rentals Wailea
- Rentals with a patio Wailea
- Beach condo rentals Wailea
- Serviced apartment rentals Wailea
- Waterfront rentals Wailea
- Townhouse rentals Wailea
- Monthly Rentals Wailea
- Villa rentals Wailea
- Hotel rentals Wailea
- Wheelchair accessible rentals Wailea
- Condo rentals Wailea
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom