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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$295/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - K (sleeps 2)
4.99 (113 reviews)
1 Bedroom, 2 Bathrooms, Sleeps 2 Adults, Not Suitable For Children
$684/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - (sleeps 8)
4.86 (123 reviews)
$440/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.93 (111 reviews)
Soooooo Close to the Beach & Completely Remodeled. Relax to the Sounds of Waves
$447/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.84 (113 reviews)
Luxury and Spacious Ground floor, 1B/ 2B, King bed, 1022 sq ft, 473 sq ft lanai
$520/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KXX (sleeps 4)
4.94 (101 reviews)
Fully-renovated 1 Bedroom Wailea Condo, Fantastic Location Close to Pools/Beach.
$340/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KXQ (sleeps 4)
4.85 (103 reviews)
Wailea Ekolu, Wailea, South Maui, Maui, Hawaii
$450/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 5)
4.8 (107 reviews)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 4-5)
$335/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
4.99 (88 reviews)
Newly Remodeled Gorgeous 1 Bed/2 Bath Villa Mountain and Partial Ocean Views
$901/nt (avg.)
Location: Polo Beach Club, Wailea
Bedrooms: 2 - KQX (sleeps 6)
4.96 (92 reviews)
2 Bedrooms, 2 Bathrooms, Sleeps 6, ground floor unit. The living room of this special spot is one of blue sky, blue ocean and palm trees swaying in the Maui breeze.
$400/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - (sleeps 4)
4.83 (100 reviews)
Oceanview Condo, 2 Bedrooms, 2 Baths, (Sleeps 4)
$400/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
4.96 (85 reviews)
Condo, 1 Bedroom, 2 Baths (Sleeps 4)
$395/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KK (sleeps 4)
4.84 (97 reviews)
This 1 bedroom 2 bath has mountain and ocean views and very secluded from others
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 4)
4.94 (87 reviews)
The magic of Maui has been waiting for You. Come and Enjoy in luxury.
$535/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - (sleeps 4)
4.89 (91 reviews)
Our condo features 2 master suites that sleep a family of 6 or 2 couples. You can enjoy the most magnificent and expansive ocean views in the complex on our 2 private lanais and experience Maui's famous spectacular sunsets every evening.
$1455/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KKTQX (sleeps 6)
4.99 (80 reviews)
Condo, 2 Bedrooms + Den, 2 Baths, (Sleeps 6)
$415/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
4.95 (83 reviews)
Ground Floor Renovated Ekahi Greenbelt 1Br/2Ba - Peaceful garden view.
$425/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - QQ (sleeps 5)
4.97 (79 reviews)
Best Located Ekolu Unit In Complex With Vaulted Ceilings, 2br/2ba And 3 Lanais
$350/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
4.91 (86 reviews)
1 Bedroom, 2 Bathroom With Ocean Views Next To The Beach
$529/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KK (sleeps 5)
4.91 (85 reviews)
Ocean & Golf Views. Fully Upgraded, Spacious & High-End, 2 Bed, 2 Bath
$369/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
4.96 (79 reviews)
Our beautiful ocean view unit is situated in upper Wailea Ekahi Village. It is a 952 square foot unit on the second floor with one bedroom and two full bathrooms.
$295/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
4.97 (78 reviews)
Enjoy Sweeping Ocean Views from this High End Remodel Top Floor Condo.
$450/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQFT (sleeps 8)
4.78 (94 reviews)
Condo, 2 Bedrooms + Other (See Description), 2 Baths, (Sleeps 8)
$668/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQX (sleeps 6)
4.9 (81 reviews)
Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)
$993/nt (avg.)
Location: Elua Village, Wailea
Bedrooms: 2 - KTTX (sleeps 4)
5 (70 reviews)
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.
$395/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 2 - (sleeps 6)
4.9 (81 reviews)
Quiet, 2 bedroom, 2 bathroom condo. Pool and AC.
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - XK (sleeps 4)
4.74 (95 reviews)
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)
$794/nt (avg.)
Location: Wailea
Bedrooms: 3 - KKQ (sleeps 6)
4.89 (76 reviews)
3 bedroom, 3 bathrooms
$450/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
4.99 (68 reviews)
Condo, 1 Bedroom, 1.5 Baths, (Sleeps 2)
$525/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 2 - (sleeps 6)
4.91 (76 reviews)
Condo, 2 Bedrooms + Convertible bed(s), 3 Baths, (Sleeps 5-6)
$1358/nt (avg.)
Location: Hoolei, Wailea
Bedrooms: 3 - KQX (sleeps 10)
4.93 (71 reviews)
Villa, 3 Bedrooms + Convertible bed(s), 3.5 Baths, (Sleeps 8-10)
$1333/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KQX (sleeps 6)
4.97 (68 reviews)
Condo, 2 Bedrooms + Den, 2 Baths, (Sleeps 6)
$475/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.89 (75 reviews)
1 Bedroom, 2 Bathroom, 4 Sleeps
$495/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - TTQXK (sleeps 5)
4.93 (68 reviews)
Condo, 1 Bedroom + Convertible Bed(s), 2 Baths, (Sleeps 4-5)
$330/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
4.94 (67 reviews)
Beautiful Condo - 945 Sq Ft located in Wailea, Maui
$218/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.79 (81 reviews)
Condo, 1 Bedroom + Convertible bed, 1 Bath, (Sleeps 2-4)
$645/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 2)
4.98 (62 reviews)
1 Bedroom, 2 Baths with Sunset Ocean Views
$565/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQ (sleeps 6)
4.98 (62 reviews)
Townhome, 2 Bedrooms, 2.5 Baths, (Sleeps 6-8)
$604/nt (avg.)
Location: Elua Village, Wailea
Bedrooms: 2 - KT (sleeps 6)
4.88 (73 reviews)
Beautiful 1,500 sf ft townhouse, 2bd/2bth, 4 minute walk to beach, pool, gym
Location: Wailea Beach Villas, Wailea
Bedrooms: 4 - KKQK (sleeps 8)
4.98 (62 reviews)
Completely Upgraded, In Pristine Condition, Comfortably Accommodates 8 Adults or
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 5)
4.98 (63 reviews)
Great Lower Village location - Spacious - Fully updated.- Aircon - Large lanai
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