
Cottage holiday rentals in Wailea
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Top-rated cottage rentals in Wailea
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Wailea cottage rentals
Cottage rentals with a hot tub

Privacy, Luxury, Ocean View Cottage, HotTub, K-Bed

Romantic and Private Cottage and Gazebo for two!

Leilani's "Leimomi" Cottage - County Licensed

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

Romantic Suite | Tropical Escape | BBQ & Hot Tub

Rustic Upcountry retreat with breathtaking views!

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS
Pet-friendly cottage rentals

3B/2B FamilyVacationComfort HawaiianaCharm Central

Grateful Casita

Maui Meadows Ocean View Cottage

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS
Private cottage rentals

Walk to small beach, charming cottage

Cute Plantation Cottage; Walk into Wailuku Town!

OCEAN VIEW Kaanapali Cottage ICC 24

Beautiful Cottage 5 Minutes From Beach

Renovated Plantation Home; Walk into Wailuku Town!

Maui -Kaanapali - International Colony Club

Remodeled 2BR | Deck | Washer/Dryer

Haiku Hideaway - Stand-alone 2 bedroom farm house
Destinations to explore
- Rentals with a sauna Wailea
- Rentals with pools Wailea
- Luxury rentals Wailea
- Rentals with a washing machine and dryer Wailea
- Condo rentals Wailea
- Hotel rentals Wailea
- House rentals Wailea
- Rentals with a kayak Wailea
- Beach condo rentals Wailea
- Villa rentals Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- Rentals with an EV charger Wailea
- Serviced apartment rentals Wailea
- Waterfront rentals Wailea
- Apartment rentals Wailea
- Fitness-friendly rentals Wailea
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- Pet-friendly rentals Wailea
- Family-friendly rentals Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Cottage rentals Maui County
- Cottage rentals Hawaii
- Cottage rentals United States
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
- Hāmoa Beach
- Maui Ocean Center
- Kaipukaihina
- Wailea Beach
- Oneloa Beach
- Puu Olai Beach
- Changs Beach
- Palauea Beach
- Old Lahaina Luau
- Maui Golf & Sports Park
- Wailau Valley
- Wailea Golf Club
- Ka'anapali Golf Courses