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Wailea Villas

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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    43 Matching Rentals in WaileaView all 340 rentals
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    LUXURY FOR LESS! Best value in Hoolei Wailea!1 / 24
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Maui Ocean View, Ground Floor, Beach House Chic1 / 23
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Air Conditioning
    • Secure Parking
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean view villa cottage 100% privacy quite isolated place . Driving to the shops of Wailea around 5 mins. Formosa Makamae Villa is a solo, quiet 700 sqft and 250 sqft deck property. An open deck facing the seaside boasts a 360 degree panoramic view from the foot of Haleakala to Molokai island....
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    Wailea, Maui 96753
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    • 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
    Rental Home - 2 Bedrooms, 2 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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    • Air Conditioning
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Washer
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Trip Advisor Guests Describe L409 as "Perfect & Well Worth the Money". Visit our website for additional pictures to see why this villa is the most popular unit there based on travelers reviews. Luxurious 3000' Panoramic Oceanview Villa Available at Owner Direct Low Prices. This breath taking...
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    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Blue Horizons K308 Wailea Beach Villas1 / 75
    (11)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 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
    <b>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 Awards published on October 18, 2016.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 8
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    Island Oasis M111 Wailea Beach Villas1 / 61
    (14)Excellent
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2012
    Spending our 35th anniversary here, in the beautiful Island Oasis Villa, could not have been more perfect.The owners of this villa know what they’re doing. Heavenly beds...
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    About this property
    <b>Island Oasis M111 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.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 2 Bathrooms, Sleeps 6
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    Aqua Lani J305 Wailea Beach Villas1 / 78
    (8)Excellent
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Children's Pool
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 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
    <b>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 published on October 18, 2016.</b> The Wailea Beach Villas is ranked...
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    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 6
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    Hoku at Ho'olei -  Grand Wailea Resort Privileges1 / 37
    (7)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Housekeeping Included
    • Hot Tub
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Sauna
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 9, 2016
    This is hands down our favorite place to stay when we come to Maui. We have stayed in Hoku at Ho'Olei four years in a row and I am already planning on our next trip! Owners...
    Reviewed November 26, 2015
    Aloha! We have stayed at Hoku Ho'Olei for the past 4 years and I have already booked my trip for July, 2016! Love this villa and the owners. Very beautiful, comfortable and all...
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    About this property
    GRAND WAILEA RENTAL PROGRAM BENEFITS FOR OUR GUESTS: * Complimentary on-demand transportation to and from The Grand Wailea Resort * Enjoy the use of all the pools, water slides, spa and restaurants at The Grand Wailea Resort * Exclusive charging privileges at The Grand Wailea Resort *...
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wailea Orchid Villa - Panoramic Views!  3 Bd/3 Ba1 / 22
    (5)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
    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Golden Mandarin D102 Wailea Beach Villas1 / 78
    (3)Very good
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 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
    <b>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 Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    Azure Azul M212 at Wailea Beach Villas1 / 77
    (2)Excellent
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 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
    <b>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 published on October 18, 2016.</b> The Wailea Beach Villas is ranked...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 6
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    Aloha Kai Suite at Wailea Beach Villas PH 2051 / 42
    (96)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Balcony
    • DVD Player
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2017
    My stayed for 5 nights in this beautiful condo. 5 stars all the way around. Everything was absolutely perfect! Great location. Easy access to beach, restaurants, shopping, and...
    Reviewed April 20, 2017
    We had a wonderful stay in the Aloha Kai Suite over spring break. The rooms were just beautiful and so nicely decorated. The location was fantastic - right by the family pool...
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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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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sandy Surf K508 Wailea Beach Villas1 / 82
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    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! 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.</b> The Wailea Beach Villas is ranked...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 6
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    Grand Seascape K407 Wailea Beach Villas1 / 66
    (10)Excellent
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>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 Awards published on October 18, 2016.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 2 Bathrooms, Sleeps 6
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    Floral Gardens Villa G102 Wailea Beach Villas1 / 76
    (9)Excellent
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Patio
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 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 October 30, 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
    <b>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 Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • DVD Player
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Bella Luna D302 Wailea Beach Villas1 / 86
    (6)Excellent
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 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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    <b>Bella Luna D302 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.</b> The Wailea Beach Villas is ranked...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Internet Access
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
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    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Sauna
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    • Washer
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Hot Tub
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    • Patio
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Air Conditioning
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Hot Tub
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    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
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    Kid friendly
    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Sauna
    • Air Conditioning
    • Parking
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Show Prices
    Amenities & Details
    • Patio
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Hot Tub
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Wailea Flight and Weather Info
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    Kahului Airport
    14.3 miles from Wailea
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