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Wailea Villas

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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in WaileaView all 218 rentals
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    LUXURY FOR LESS! Best value in Hoolei Wailea!1 / 48
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Ho'olei at Grand Wailea - Deluxe Ocean View1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    We stayed in this condo directly over the private pool. We had three couples and a 14 month old and the space was perfect! The location is great, 10 min walking distance to...
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    About this property
    Spend your vacation at Ho'olei luxury villas at Grand Wailea on Maui! Located just minutes from the world-class Grand Wailea Resort Hotel & Spa on Maui's southern shore, each two-story villa offers a luxurious home in paradise. Every villa has three bedrooms and 3.5 baths with finely appointed...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Hot Tub
    • Sauna
    • Ocean Views
    • Mountain Views
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax and enjoy your stay at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui. Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean views from both upper and lower...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2BR/2BA Condo in Wailea located in the amazing Grand Champions Villas complex. Only a 5 minute walk to the beach, Grand Champions provides a luxurious, relaxed vibe in the beautiful town of Wailea. Close to numerous restaurants, shops and beaches. Relax in the two pools on property or...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wailea Orchid Villa - Panoramic Views!  3 Bd/3 Ba1 / 21
    (6)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
    Reviewed 4 weeks ago
    We've just returned from our trip. We had an amazing stay at this property in Wailea. It is so spacious, the kitchen was stocked with EVERYTHING we needed for daily meal prep...
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    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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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sunny Surf E301 at Makena Surf1 / 50
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Internet Access
    • Washer
    • Grill
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 October 2015
    Once entering the property which is quite secure, and meeting the friendly and helpful owner, you are taken through a wonderful tropical and well maintained garden around a...
    Reviewed 23 May 2015
    When I was planning our family vacation for my wife and 2 adult sons, I spent countless hours researching, talking to friends, etc. As I am a supporter of Tripadvisor, I also...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-2464-02 County of Maui Short-Term Rental License #Hotel-Zoned Sunny Surf E301 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Floral Gardens Villa G102 Wailea Beach Villas1 / 50
    (9)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2015
    My husband and I, along with our baby stayed in this luxury unit in November. The unit has fabulous access to outside lanai's and grass areas. The kitchen was equipped as if it...
    Reviewed 31 October 2013
    Very spacious, perfect for a family. This villa is finished with high quality furniture/appliances etc. it had everything you need and more! the property is secure, quiet and...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-1168-01 Floral Gardens Pool Villa G102 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Bella Luna D302 Wailea Beach Villas1 / 50
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2013
    One of the best vacation rentals we've ever had the pleasure of enjoying. When you calculate the price of nearby hotels, this 3 bedroom/3.5 bath condo was well worth the price...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-6368-01 Bella Luna D302 is the ultimate premiere top-tier villa panoramic ocean view residence within the beachfront Wailea Beach Villas Resort. D302 Bella Luna is scheduled to have new ownership as of fall 2018. Once the purchase is...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Hale Makena Maui1 / 24
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Hot Tub
    • Internet Access
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With its stunning Pacific views and sought-after location, Hale Makena Maui is one of the most impressive 4-bedroom Maui villas available. This resplendent villa is found beachside in Makena, just south of the ultra-luxurious enclave of Wailea; escape the crowds in favor of a more tranquil, yet...
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    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Golden Mandarin D102 Wailea Beach Villas1 / 50
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 January 2015
    We have been coming to Wailea for the past 15 years and the Golden Mandarin was by far the best place we have ever stayed. The Villa was exquisite and was stocked with every...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-0880-02 Golden Mandarin Pool Villa D102 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Aqua Lani J305 Wailea Beach Villas1 / 50
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2014
    We booked Aqua Lani J305 through Cary Ritt at Maui Vacation Advisers, and the villa management is provided throught Tropical Villa Vacations. From beginning to end, top to...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-9680-01 Aqua Lani J305 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Azure Azul M212 at Wailea Beach Villas1 / 50
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2017
    Everything about this condo and resort is 1st class. The location of the unit itself (450) is perfect. The huge lanai overlooks the pool if you are trying to keep your eye on...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-1360-02 Azure Azul M212 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sandy Surf K508 at Wailea Beach Villas1 / 50
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-4016-01 Sandy Surf K508 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Grand Seascape K407 Wailea Beach Villas1 / 50
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-9024-01 Grand Seascape K407 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...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orient Pacific Suite J505 at Wailea Beach Villas1 / 50
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 October 2017
    It was my family's second time staying at the Wailea Beach Villas in J505 and it was perfect as usual! There were 3 spacious, luxurious bedrooms, each with their own bathroom...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-9936-01 Orient Pacific Suite J505 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'...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sea Breeze Suite J405 at Wailea Beach Villas1 / 50
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2017
    My wife and I along with our 2 sons and their wives, just returned from a week at Wailea Beach Villas J405. From the moment I first contacted Tropical Villa Vacations all the...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-7632-01 Sea Breeze Suite J405 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...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Aloha Kai Suite at Wailea Beach Villas PH 2051 / 42
    (99)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This is a fabulous place for a family gathering: three big bedrooms, each with its own bath so each one can be closed off as a private suite. The kitchen is equipped with...
    Reviewed 21 January 2018
    This condo is simply amazing! From the fabulous kitchen, to the beautifully decorated living space and on into the bedrooms everything is classy and comfortable. Having three...
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    About this property
    Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. The Aloha Kai Suite is elegant and refined to the last detail--sophisticated furnishings and spectacular art. Formal entry hall. Spacious living room. Formal dining with...
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mer Et Soleil K408 Wailea Beach Villas1 / 100
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-7504-01 Mer Et Soleil K408 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...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    96753, Wailea, Maui
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blue Horizons K308 Wailea Beach Villas1 / 100
    (11)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Private Outdoor Pool (Heated)
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2015
    Our family had such a wonderful vacation here, been going to Maui for over 20 years this was definitely our favorite place, everyone was comfortable with their accommodations...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-3120-01 Blue Horizons K308 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...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beachfront Estate on Kamaole I / Charley Young Beach1 / 15
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 December 2017
    The accommodation is ideally located 20 metres from the beach. This is the second time in three years a group of family and friends has booked the entire suite of apartments...
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    About this property
    Dolphins Point Maui is the perfect beach house for your family or group vacation, with 4 bedrooms & 4 bathrooms split into three private suites. The property is ideally situated directly on a beautiful white sand beach - literally the lawn ends and the sand begins! You can be settled at the beach...
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    Location Information
    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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