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Wailea Villas

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    ₹ 83,199 Average
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    Wailea is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    24 Matching Rentals in WaileaView all 334 rentals
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    Spectacular 3rd Row at Ho'olei with Ocean Views1 / 33
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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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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    Amenities & Details
    • 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 17 June 2018
    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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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Due to ongoing changes to the General Exercise Tax percentage in Hawaii, bookings may be subject to an adjustment or higher tax percentage. 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...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    *Cancellation Discount* To fill, rate reduced to just $200/night Dec. 13-22/18*1 / 39
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2018
    Our family had an amazing time at Chris and Kristin's villa. The kids loved the pool, we loved the golf course. The kids loved exploring the complex's gardens and we loved...
    Reviewed 20 October 2018
    This is an incredibly well-stocked condo with attractive furnishings, comfortable beds, unique decor (many of which are owner-created), and in optimal location within the Grand...
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    About this property
    This is Wailea Living! Nestled in a private and secluded enclave between the Wailea Blue Course and the Wailea Tennis Club, the Wailea Grand Champions Villas are where travelers can golf, play tennis, be pampered at the Wailea Grand Spa, whale watch or turtle spot, or soak up the sun, snorkel,...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    LUXURY FOR LESS! Best value in Hoolei Wailea!1 / 24
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
    • DVD Player
    • Sauna
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Highly recommend . Beautiful house , it's a good place for a few family to stay , if you like to save money,and cook is the one you should rent
    Reviewed 22 June 2017
    This villa in Ho'olei was beautiful--wonderful location with easy access to restaurants, shopping, and of course, the beach! The pool was relaxing, not crowded at all. Some of...
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    About this property
    TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 square foot villa with large...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the U.S....
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    Wailea, Maui 96753
    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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 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 located on Maui island, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the U.S....
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    Location Information
    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mer Et Soleil K408 Wailea Beach Villas1 / 50
    (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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the...
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    Wailea, Maui 96753
    Holiday Rental House - 4 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018!...
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    Wailea, Maui 96753
    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 1 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 30 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 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 20 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the U.S....
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 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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    • 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in...
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    Wailea, Maui 96753
    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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    • 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the...
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    Wailea, Maui 96753
    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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    • 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the U.S....
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 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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    Beachfront Estate on Kamaole I / Charley Young Beach1 / 15
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • 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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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    • 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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Blue Horizons K308 Wailea Beach Villas1 / 50
    (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, ranked #1 Best Luxury Destination in the USA and #2 Best Beaches in the USA by U.S News & World Report published April 19, 2018! Maui island was also voted #2 Best Island in the...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Aloha Kai Suite at Wailea Beach Villas PH 2051 / 42
    (101)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Mountain Views
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    This was a fantastic unit for a family of 4. Very clean and comfortable, well appointed within the resort. Would definitely book again and recommend to friends. Owners were...
    Reviewed 20 July 2018
    We stayed for 6 nights in Aloha Kai Suite-3 berdroom in the Penthouse in July 2018 with our 3 teenagers. The condo had a nice view of the ocean and was decorated really nicely...
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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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    Location Information
    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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