Wailea Vacation Rentals

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Showing top 200 rentals. Use the Search Filters button to narrow the choices based on your preferences.
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Location: Elua Village, Wailea
Bedrooms: 2 - KQT (sleeps 4)
condo, 2 Bedrooms, 2 Bathrooms, Sleeps 5. In October 2019, we completed a 6-month, top-to-bottom, remodel of our condo! All the windows and sliding lanai doors were replaced, and we even added another sliding door in the living room to expand the ocean view!
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - K (sleeps 2)
1 Bedroom, 2 Bathrooms, Sleeps 2 Adults, Not Suitable For Children
from $150/nt
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
Condo, 1 Bedroom + Convertible bed, 1 Bath, (Sleeps 2-4)
from $995/nt
Location: Wailea Beach Villas, Wailea
Bedrooms: 3 - KTQT (sleeps 8)
Wailea Beach Villas condo, 3 Bedrooms, 3 Baths, Sleeps 6-8, Great Reviews.
from $125/nt
Location: Grand Champions, Wailea
Bedrooms: 0 - KX (sleeps 4)
Condo, Studio + Convertible bed, 1 Bath, (Sleeps 2-3)
from $231/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - KQ (sleeps 4)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KXX (sleeps 4)
Renovated 1 Bedroom Wailea Condo, Fantastic Location Very Close to Pool/Beach.
from $175/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - (sleeps 4)
Oceanview Condo, 2 Bedrooms, 2 Baths, (Sleeps 4)
from $220/nt
Location: Grand Champions, Wailea
Bedrooms: 2 - KF (sleeps 6)
The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort.
from $250/nt
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KK (sleeps 4)
This 1 bedroom 2 bath has mountain and ocean views and very secluded from others
from $299/nt
Location: Grand Champions, Wailea
Bedrooms: 2 - KTX (sleeps 5)
2 bed/2 bath renovated villa with treetop views of pool and tropical grounds
from $278/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 5)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 4-5)
Location: Ekahi Village, Wailea
Bedrooms: 2 - QKX (sleeps 6)
Fully-renovated 2 Bedroom Wailea Condo, Fantastic Location Close to Pools/Beach.
from $189/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KXQ (sleeps 4)
Wailea Ekolu, Wailea, South Maui, Maui, Hawaii
from $159/nt
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
1 Bedroom, 2 Baths, Sleeps 4
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KX (sleeps 4)
Luxury and Spacious Ground floor, 1B/ 2B, King bed, 1022 sq ft, 473 sq ft lanai
from $950/nt
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KKTQX (sleeps 6)
Condo, 2 Bedrooms + Den, 2 Baths, (Sleeps 6)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
Condo, 1 Bedroom, 1.5 Baths, (Sleeps 2)
from $225/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KX (sleeps 2)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)
from $525/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - QKX (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 5-7)
from $420/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - KTX (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)
from $450/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQFT (sleeps 8)
Condo, 2 Bedrooms + Other (See Description), 2 Baths, (Sleeps 8)
from $515/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - KKT (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)
from $320/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
Soooooo Close to the Beach & Completely Remodeled. Relax to the Sounds of Waves
Location: Grand Champions, Wailea
Bedrooms: 2 - KK (sleeps 6)
2 BD/2 BA Remodeled/Updated Wailea Condo w/Ocean, Golf Course & Mountain Views
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KQX (sleeps 6)
Condo, 2 Bedrooms + Den, 2 Baths, (Sleeps 6)
Location: Elua Village, Wailea
Bedrooms: 1 - K (sleeps 2)
1 Bedroom, 2 Bathrooms With Ocean Views. This top floor 1280 sq. ft. Beach House with wood accented vaulted ceilings and lanai in a 2-story building has ocean views from South of Lanai to the tip of West Maui with breathtaking sunsets.
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
Enjoy Sweeping Ocean Views from this High End Remodel Top Floor Condo.
Location: Location
Bedrooms: 3 - KQX (sleeps 10)
Villa, 3 Bedrooms + Convertible bed(s), 3.5 Baths, (Sleeps 8-10)
from $650/nt
Location: Elua Village, Wailea
Bedrooms: 2 - KTTX (sleeps 5)
Condo, 2 Bedrooms + Convertible Bed(s), 2 Baths (Sleeps 4-6). Totally remodeled (Fall, ’15). Custom teak cabinets, granite counter tops, open kitchen, spacious showers and top of the line appliances. The 180 degree view and quiet location make this the perfect vacation condo.
Location: Grand Champions, Wailea
Bedrooms: 2 - (sleeps 4)
Condo, 2 Bedrooms(s), 2 Baths, (Sleeps 4)
from $270/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
Condo, 1 Bedroom, 2 Baths (Sleeps 4)
from $300/nt
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
Newly Remodeled Gorgeous 1 Bed/2 Bath Villa Mountain and Partial Ocean Views
from $425/nt
Location: Mana Kai, Wailea
Bedrooms: 2 - (sleeps 6)
from $205/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KX (sleeps 2)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2)
from $239/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
Ekahi 53d is a 1-bedroom luxury condo with a stunning ocean view from the lanai.
from $330/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQX (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)
Location: The Palms at Wailea, Wailea
Bedrooms: 2 - (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 3 Baths, (Sleeps 5-6)
from $349/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - K (sleeps 4)
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - K (sleeps 4)
1 bedroom, 2 full bathrooms, sleeps 2-4
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