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Vacation Rentals in Wailea, HI

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    Travellers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 16
    4.5 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 16
    4 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    1 / 16
    4.5 of 5 stars (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    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... View all property information
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    Wailea, Maui 96753
    1 / 19
    4 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    About this property
    Please ask about our Spring 2016 Discounted Rates!! Wailea Ekahi Village 4E second floor condominium is adjacent to a landscaped ravine and has beautiful tropical garden views. This location provides a quiet location, away from any road noise and a couple minutes' walk to the main swimming pool,... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second floor. Sitting on the lanai at sunset, we feel the... View all property information
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    Wailea, Maui 96753
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Wailea Elua Village #2010 is located on one of the buildings corners, giving you ocean views and property from the master lanai and the main lanai which may also be accessed via the guest bedroom. Recently added to the condo area large new flat screen TV, iPod docking station, new couch and living... View all property information
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    Wailea, Maui 96753
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wailea, Maui 96753
    1 / 23
    4 of 5 stars (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • x
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    About this property
    Great Spring 2016 Rates - Please Inquire ! Wailea Ekahi 38B is a charming condominium furnished with a King bed in the master bedroom, queen sofa sleeper in the living room, is fully air conditioned and has free high speed wireless internet access. There are ceiling fans throughout, Flat screen TV... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 stars (21) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • x
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    • x
    About this property
    About this condo: Wailea Elua Village #1402 is a 2nd story, one bedroom, one bath oceanfront condo complete with a fully remodeled kitchen, new carpet and a sofa sleeper. Enjoy the complimentary wireless internet service on your lanai as you enjoy the beautiful view of the sun-kissed Ulua Beach.... View all property information
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    Wailea, Maui 96753
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    1 / 46
    5 of 5 stars (13) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    <b>Wailea Sunset Bungalow is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> Visit The NEW Wailea Sunset Bungalow! Extensively renovated, updated, and re-decorated from top to bottom, inside and out! Please read the effusive guest... View all property information
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    Wailea, Maui 96753
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Washer
    • Ocean Views
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    QUIET PRIVACY IN PARADISE This is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations in the property. Often the only sound you will hear is the waves crashing on the nearby beaches. The Palms at Wailea is one of the upscale... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    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
    1 / 19
    3 of 5 stars (1) Average
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
    • Satellite TV
    • Waterfront
    • Terrace
    • Air Conditioning
    • Internet Access
    • Balcony
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Wailea Ekahi 14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home ! You will feel like you are on top of the world as you look out from the second floor onto the Greenbelt and over the blue Pacific Ocean. The... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    About this condo: Wailea Elua Village #1510 is a spacious two-bedroom, two-bath ocean view condo in located just a short walk away from the property's central pool, Jacuzzi and paddle tennis courts. Newly replaced carpet, living room furniture, granite counter tops and refrigerator help make this... View all property information
    Location Information
    Wailea, Maui 96753
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Satellite TV
    • Balcony
    • Grill
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Surround yourself with the lush, natural beauty of Hawaii, starting with your choice in accommodations. Maui Breeze Retreat is a luxurious, privately-owned townhome nestled in Ho’olei, located near the Grand Wailea Hotel & Spa and Four Seasons Resorts on the beautiful island of Maui. Your... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you need for your Maui vacation. We've stocked our... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • DVD Player
    • Hot Tub
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Notes from the Owner: Wailea Elua Village #801 is located in the center of the Elua Village just across from the small pool and Jacuzzi area and just steps to the paddle court. Enjoy ocean views as well as secluded garden views from this quiet ground floor, two bedroom, two bath unit. The lanai... View all property information
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    Wailea, Maui 96753
    1 / 83
    4 of 5 stars (2) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Internet Access
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    <b>Coco Palms Pool Villa D101 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October... View all property information
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    Wailea, Maui 96753
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    1 / 16
    3.5 of 5 stars (11) Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Wailea, Maui 96753
    1 / 94
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    • x
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    • ?
    About this property
    <b>Royal Ilima A201 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October 20, 2015.... View all property information
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    Wailea, Maui 96753
    1 / 82
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    <b>Sandy Surf K508 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October 20, 2015. In... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (21) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Outdoor...
    • Wi-Fi
    • DVD Player
    • Grill
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Notes from the Owner: Come relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles of pristine beaches, magnificent sunsets and renowned cuisine, Wailea will surely be your ultimate vacation experience! The active vacationer can tee it up on one of five... View all property information
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    Wailea, Maui 96753
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Wailea Grand Champions is minutes away from some of the nicest five-star resorts on Maui. The Four Seasons, Grand Wailea, and Fairmont Kea Lani are all within a five minute drive. That should give you a perspective on what kind of beaches, restaurants, golf courses, and shopping you are nearby!... View all property information
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    Wailea, Maui 96753
    1 / 84
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
    • x
    • Smoking allowed
    • ?
    About this property
    <b>Sun Splash C301 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October 20, 2015. In... View all property information
    Location Information
    Wailea, Maui 96753
    1 / 24
    5 of 5 stars (21) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Mountain Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located "down in front" on the water at Wailea Elua Village, this Second Floor AIR CONDITIONED Condominium has received a complete Custom-Designed Interior Renovation. Everything has been updated - flooring, furniture, artwork, lighting, and fixtures - including a fully upgraded kitchen with... View all property information
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    Wailea, Maui 96753
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wailea, Maui 96753
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    • Housekeeping...
    • Ocean Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    <p>Wailea Ekahi 20F is a 2 bedroom unit featuring panoramic ocean views, a great, quiet location with a short, 2 minute walk to Keawakapu Beach. As new owners, we welcome you to enjoy our condo and all that it has to offer!</p> <p>Wailea Ekahi Village is a premier ocean front condominium... View all property information
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    Wailea, Maui 96753
    1 / 74
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    • x
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    • ?
    About this property
    <b>Orient Pacific Suite J505 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Satellite TV
    • Waterfront
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    With your best interest in mind, your dream vacation, we have the biggest inventory of units to offer at Makena Surf than any other listing on Flipkey. Call or email with your ideal travel dates and you'll quickly be able to know 1) which units are available for your dates, 2) prices in different... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Quiet condos located in the heart of Wailea w/ golf and tennis “out the door”. Wailea Grand Champions is an 11 acre condo property amid the Wailea Blue Gold Course and next to the Wailea Tennis Club. Please be sure to tell us how many are your party, how many adults and how many children w/ their... View all property information
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    Wailea, Maui 96753
    1 / 39
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Terrace
    • Balcony
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Ocean Bliss is a stunning beachfront estate that provides the best of all worlds...Privacy and ocean access as the house borders South Maui's Polo Beach with it's golden sands and shallow swimming area on one side of the villa and a dramatic lava rock beach on the other side. The vistas of the sea... View all property information
    Location Information
    Wailea, Maui
    1 / 37
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Children's Pool
    • Waterfront
    • Housekeeping...
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    If you prefer spaciousness and the utmost in comfort for your family, then instead of getting two or three hotel rooms, this property offers an ideal alternative. Every superlative applies to this property but let's just say it's the ultimate residence resort in all of Hawaii. Wailea Beach Villas... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Waterfront
    • Ocean Views
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    There's no doubt this is the best beachfront choice on Maui if you have 6-8 persons, This long-time favorite condo resort on Maui, Makena Surf, is now better than ever with recently renovated units and wonderful "semi-private" kid-friendly beaches. Please be sure to tell us how many are in your... View all property information
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    Wailea, Maui 96753
    1 / 31
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    DETAILS - POLO BEACH CLUB: - 2-bedroom/2-bath condos that are offered as 1-bedroom units during parts of the year. - "Oceanfront" and "prime oceanfront" categories offered, the latter being in the "front row", but all units offer oceanviews from both the living area and the master suite of each... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 stars (5) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • DVD Player
    • Hot Tub
    • Internet Access
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    HO'OLEI VILLAS: 3-bedroom 3.5-bath luxury vacation villas Gated residential condo resort w/ maximum privacy and security in the Wailea area, Wailea Beach walking distance away Fully equipped gourmet kitchens Spacious living area with sliding doors that lead out to a large lanai Large deck area... View all property information
    Location Information
    Wailea, Maui 96753
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Ocean Views
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located on 33 acres of beautiful terraced property with breathtaking landscaped grounds in the heart of world renowned Wailea, Maui. Our 1 bedroom, 2 bath, fully-equipped Condo has a lovely ocean view and is located just a short stroll to the beachfront pool & pavilion that is situated on the... View all property information
    Location Information
    Wailea, Maui 96753
    1 / 25
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Mountain Views
    • Children's Pool
    • Hot Tub
    • DVD Player
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This spacious, professionally decorated villa has all the comforts you expect from a five star experience. The world renowned Grand Wailea and Four Seasons Resorts are located across the street, offers a world class spa, shopping and beach. Whether you group has many children, adults or seniors,... View all property information
    Location Information
    Wailea, Maui 96753
    1 / 17
    5 of 5 stars (2) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Washer
    • DVD Player
    • Children's Pool
    • Air Conditioning
    • Sauna
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    PLEASE NOTE: OUR CALENDAR APPEARS OPEN BECAUSE WE OWN 5 HOMES AT THE HO'OLEI RESORT. IN MOST CASES, I DO HAVE A HOME AVAILABLE! Come enjoy our Luxury Residence in what we call our Executive Model! This home is the Hibiscus Model, which is the largest home at Ho'olei (3,301 sq. ft. and a 686 sq.... View all property information
    Location Information
    Wailea, Maui 96753