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Holiday Rentals in Wailea

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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 211 Rentals in Wailea
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    WAILEA GRAND CHAMPION, #180^1 / 16
    (13)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cloud 9 Beach House with Pool1 / 21
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 1 Bedroom 2 Bathroom remodeled unit in Quiet Building 5 at Kamaole Sands in Kihei, Maui. Sleeps 2. We are a 2-3 minute walk to beautiful Kamaole Beach III. Our building is located in quiet building 5 on the 2nd floor. Our unit is close to the elevator but far enough away to not hear it....
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Washer
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious two bedroom condo at the Wailea Grand Champions in the heart of Wailea in South Maui. Two spacious bedrooms and a large living area make this condo the perfect Maui getaway. The master bedroom has a king bed and a full bath en-suite. The second bedroom has two twin beds. The living area...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Sometimes I feel like our guests say it best. Here is one of my recent guest book entries: 'We just enjoyed two weeks of complete relaxation at this wonderful condo unit in the best complex we have stayed at in Maui. The view from the living room and lanai is outstanding, and allowed us to...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Wailea Luxurious Beachfront  2br,2ba on Polo Beach1 / 24
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Polo Beach Club sits on quiet Polo Beach. It is a unique building located within feet of the beach. Our home is a completely remodeled 2 bedroom 2 bath unit. We always provide daily maid service and upon arrival you will receive a complimentary fruit basket. When you first enter our home look...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Washer
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful two level residential home located in South Kihei, Maui. The 3 larger bedrooms have their own in suite bathrooms. The 2 smaller bedrooms share the 4th bathroom. 2 living rooms. 2 car garage Interior Square Footage: 2600 SF Exterior Space: Covered Upper Deck: 500 SF Covered Lower Patio:...
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    Wailea, Maui 96753
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the property is exceptional...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Coco Palms Pool Villa D101 at Wailea Beach Villas1 / 83
    (2)Very good
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coco Palms Pool Villa D101 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bathrooms, Sleeps 6
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    Wailea Orchid Villa - Panoramic Views!  3 Bd/3 Ba1 / 21
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Internet Access
    • Cable/satellite TV
    • Children's Pool
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Wailea Beach Villas is the #1 Specialty Lodging in Wailea' - Trip Advisor 'Wailea Beach Villas is one of the top 100 hotels in the USA' - Conde Nast Readers Choice Award The Wailea Orchid is an amazing 3 bedroom / 3 full baths penthouse villa located in the prestigious Wailea Beach Villas....
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    A bright and spacious floor plan greets you as you enter this third floor property. With glass walls that vanish to reveal a beautiful covered lanai, the lovely outdoor space merges with the homes interior to create more room for you and your guests to take advantage of. The open floor plan...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Amazing Wailea Surf Villa at Wailea Beach Villas1 / 24
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unbelievable 2 bedroom plus den / 2 bath penthouse villa located in the prestigous Wailea Beach Villas. Second floor location with 2000 interior square feet and 375 square foot covered lanai. Formal entry hall with artwork. Spacious living room with Tommy Bahama furniture. Dining room with table...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two bedrooms and two baths in this garden view condo. The Master bedroom has a king bed and the second bedroom has a queen bed, allowing this unit to sleep up to four people. This ground floor unit is tiled in all of the common areas and carpeted in the bedrooms. The living area is a great place to...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    WAILEA EKAHI, #22D1 / 16
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Ekahi Village is a beautifully terraced property located at the entrance to the resort community of Wailea. This relaxing low-density property consists of 54 two-story buildings spread out over thirty-four acres of immaculate tropical landscaping. Keawakapu Beach fronting the property is...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the property is exceptional...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book with confidence, this stunning, 2 bedroom, 2 bathroom (1200 sq. ft) condo that has been completely remodeled. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7. This condo offers...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About this condo: Wailea Elua Village #106 is a second floor, two bedroom-two bath, ocean view condo with a large lanai complete with a sun shade screen. It has a king bed in the master bedroom and a queen bed in the guest bedroom. This unit can be rented as a one bedroom during non peak periods....
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the property is exceptional...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Wailea Sunset Estate1 / 67
    (13)Very good
    Studio, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Sunset Estate is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. Wailea Sunset Estate, one of our...
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    Wailea, Maui 96753
    Holiday Rental House - 6 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Mountain Views
    • Patio
    • Hot Tub
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Palms at Wailea condo complex is one of the most elegant developments in the exclusive and breathtaking resort community of Wailea, Maui. Our condo (Unit #1603) was custom remodeled, designed, and decorated as our personal home, hence it is exquisitely upgraded and superior to typical rentals....
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated one-bedroom oceanfront unit in Elua Village with all the amenities including free wi-fi, flat screen TVs, fully appointed kitchen, and more... Elua Village direct oceanfront, #1402 - Come and experience the magic of Wailea, Maui! Our one-bedroom condominium has been renovated with all...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A note from the owner: This rare 3 bedroom ocean view, golf course view condo has been completely remodeled in 2011. It the absolute best location in the Grand Champions Villas boasting granite countertops and stainless steel appliances. Relax on the grand lanai and watch water sunsets year round....
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    Wailea, Maui 96753
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the property is exceptional...
    View all property information
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Balcony
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Intimate couples retreat on one of the best beaches on Maui. This is a one-of-a-kind condo. Tropical elegance and luxury highlight this unit at the Ekahi Village community. Stunning ocean and up-country views combine with a quiet privacy to make this the ideal destination for couples seeking a...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please come visit our 'Little Slice of Heaven' on Maui's Makena Coast! Relax and enjoy the great beaches, sunshine, and surf you can comfortably snorkel or boogie board in almost every day. Two large fresh water pools, two hot tubs, four tennis courts, plus a tropical setting with beautiful foliage...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    EPIC OCEAN VIEW - LUXURY AT IT'S BEST1 / 75
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our luxury, two bedroom, two bath, Non-Smoking, Maui condo is an owner direct rental located in Maui Kamaole. Maui Kamaole is a luxury AAA, three-diamond condo resort in sunny, south Maui, Hawaii. This low-rise, townhouse-style complex is directly across from the beach and ocean and overlooks the...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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