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: The Palms at Wailea, Wailea
Bedrooms: 1 - K (sleeps 2)
1 Bedroom, 2 Bathrooms, Sleeps 2 Adults, Not Suitable For Children
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!
from $160/nt
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
Condo, 1 Bedroom + Convertible bed, 1 Bath, (Sleeps 2-4)
from $1095/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 $135/nt
Location: Grand Champions, Wailea
Bedrooms: 0 - KX (sleeps 4)
Condo, Studio + Convertible bed, 1 Bath, (Sleeps 2-3)
from $249/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 $265/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - KQ (sleeps 4)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)
from $225/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - (sleeps 4)
Oceanview Condo, 2 Bedrooms, 2 Baths, (Sleeps 4)
from $300/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: 1 - KXX (sleeps 4)
Renovated 1 Bedroom Wailea Condo, Fantastic Location Very Close to Pool/Beach.
from $295/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 $218/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KXQ (sleeps 4)
Wailea Ekolu, Wailea, South Maui, Maui, Hawaii
Location: Ekahi Village, Wailea
Bedrooms: 2 - QKX (sleeps 6)
Fully-renovated 2 Bedroom Wailea Condo, Fantastic Location Close to Pools/Beach.
from $350/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 $225/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KX (sleeps 2)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)
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 $179/nt
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
1 Bedroom, 2 Baths, Sleeps 4
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
Condo, 1 Bedroom, 1.5 Baths, (Sleeps 2)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KKTQX (sleeps 6)
Condo, 2 Bedrooms + Den, 2 Baths, (Sleeps 6)
from $385/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQFT (sleeps 8)
Condo, 2 Bedrooms + Other (See Description), 2 Baths, (Sleeps 8)
from $600/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - QKX (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 5-7)
from $1035/nt
Location: Location
Bedrooms: 3 - KQX (sleeps 10)
Villa, 3 Bedrooms + Convertible bed(s), 3.5 Baths, (Sleeps 8-10)
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
from $430/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - KTX (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)
from $290/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
Condo, 1 Bedroom, 2 Baths (Sleeps 4)
from $450/nt
Location: Mana Kai, Wailea
Bedrooms: 2 - (sleeps 6)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KQX (sleeps 6)
Condo, 2 Bedrooms + Den, 2 Baths, (Sleeps 6)
from $247/nt
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
Newly Remodeled Gorgeous 1 Bed/2 Bath Villa Mountain and Partial Ocean Views
from $525/nt
Location: Ekahi Village, Wailea
Bedrooms: 2 - KKT (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)
from $725/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.
from $215/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KX (sleeps 2)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2)
Location: Grand Champions, Wailea
Bedrooms: 2 - KK (sleeps 6)
2 BD/2 BA Remodeled/Updated Wailea Condo w/Ocean, Golf Course & Mountain Views
from $350/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQX (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)
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: Grand Champions, Wailea
Bedrooms: 2 - (sleeps 4)
Condo, 2 Bedrooms(s), 2 Baths, (Sleeps 4)
Location: The Palms at Wailea, Wailea
Bedrooms: 2 - (sleeps 6)
Condo, 2 Bedrooms + Convertible bed(s), 3 Baths, (Sleeps 5-6)
from $250/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - QQ (sleeps 6)
Best Located Ekolu Unit In Complex With Vaulted Ceilings, 2br/2ba And 3 Lanais
from $425/nt
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
1 Bedroom, 2 Bathroom, 4 Sleeps
from $499/nt
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - K (sleeps 4)
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