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Wailea House Rentals

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    $1,243 Average
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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    24 Matching Rentals in WaileaView all 334 rentals
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    Amazing OCEAN & CINDER CONE view MAKENA South Maui. Experience old Hawaii home1 / 11
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Cloud 9 Beach House with Pool  JULY 25th - AUG 1st open1 / 21
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Royal Ilima A201 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is ranked No. 3...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    One-of-a-Kind Maui Getaway1 / 28
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Mountain Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 27, 2017
    Our family booked this home after much time searching various websites for something that would fit our needs. We were a group of 4 adult couples and one toddler looking for...
    Reviewed January 28, 2017
    The house is beautiful, located in the best are of Maui, with killer views!!! Every thing in the house is spotless. Its better than a 5 star hotel!!!
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    About this property
    This One-of-a-Kind Maui Getaway is just the vacation destination you have been dreaming of! Owner and architect Kyron Brimmer, designed this unique and modern 4 bedroom, 4 bath Hawaiian style home with the guest in mind. From pencil sketch to sustainable masterpiece, it captures Maui’s tropical...
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    Wailea, Maui 96753
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Castaway Cove C201 at Wailea Beach Villas1 / 86
    (2)Excellent
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2016
    Really cannot think of any negatives. The location of the villa was terrrfic; it was well appointed and staff was superb.
    Reviewed August 14, 2014
    We rented Castaway Cove, Unit C201 at the Wailea Beach Villas on Maui in July 2014. This unit is managed by Tropical Villas Vacations. Our first visit to Maui and...
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    About this property
    Castaway Cove C201 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is ranked No....
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    Maui Ocean Palms-Luxury  Wailea  Home wPool, Views1 / 29
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 11, 2017
    Our family of four arrived at Maui Ocean Palms for a nine night stay starting on May 26th 2017. As we drove up we were met with the sound of waterfalls as the landscape around...
    Reviewed July 27, 2014
    We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
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    About this property
    Note: *** Our calendar is always up to date. Low Season Rate (Apr 16 - Dec 15) $395.00 per night High Season Rate (Dec 16 - Apr 15) $450.00 per night Are you looking for a quiet peaceful alternative vacation experience away from the hotel zone but minutes away from South Maui's best beaches,...
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    Wailea, Maui 96753
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Regal Mandalay M511 Wailea Beach Villas1 / 77
    (7)Excellent
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 2013
    We had a wonderful time staying here. Tropical Villa Vacations does such a great job of taking care of the details. We loved the condo. So much so we had a hard time getting...
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    About this property
    Regal Mandalay M511 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is ranked No....
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    Wailea, Maui 96753
    Rental Home - 2 Bathrooms, Sleeps 6
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    Wailea Sunset Bungalow1 / 46
    (13)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 3, 2014
    We stayed here 7 nights. It was as advertised: gorgeous sunsets, well-stocked, great outdoors with lawn, chairs, hammock, dining table. We did not try getting into the water...
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    About this property
    Wailea Sunset Bungalow 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. Visit The NEW Wailea Sunset...
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    Wailea, Maui 96753
    Rental Home - 1 Bathroom, Sleeps 4
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    Bali Hai Pool Villa F102 at Wailea Beach Villas1 / 91
    (4)Very good
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Patio
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bali Hai Pool Villa F102 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    Coral Gardens at Makena Bay1 / 60
    (1)Excellent
    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2015
    This was our fourth trip to Maui and it was the best. Thanks to Coral Gardens in Makena. The luxury home is perched on Makena Bay ('turtle town') and did not disappoint. We were...
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    About this property
    Coral Gardens Estate at Makena Bay is a legal permitted short-term vacation rental home. The permit license number is: STKM 2013/0011. The transient tax ID number is: TA-*******-0368-01. Coral Gardens Estate at Makena Bay is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 8
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    Sea Breeze Suite J405 at Wailea Beach Villas1 / 80
    (2)Excellent
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 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
    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 Awards published on October 18, 2016. The Wailea Beach Villas is ranked...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AUGUST 26th - 31st still open Come stay with us here in sunny south Maui at our beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around covered deck is perfect for indoor/outdoor style island living....
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Rainbow Deluxe1 / 20
    (41)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Internet Access
    • Hot Tub
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 1, 2017
    You won't need to look any further; stay here. The owner has gone through great lengths to ensure a perfect stay. Anything you can think you may need is provided. This...
    Reviewed February 18, 2017
    Upon arriving at Rainbow Deluxe we were exhausted. We were so delighted to open the fridge and see essentials already for us! This condo is clean and centrally located. From the...
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    About this property
    Visit www.rainbowdeluxe.com for more info! Rainbow Deluxe is a standout 2 bedroom / 2 bath vacation home conveniently located in Maui Meadows, along the south shore of Maui, Hawaii. This 700 square foot luxury Polynesian pole cottage sits on its own quarter acre, private driveway entrance, ideally...
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    Wailea, Maui 96753
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Turquoise Cove G301 at Makena Surf1 / 62
    (5)Excellent
    Studio, 5 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2017
    If you want a gorgeous oceanfront (3rd floor of a 3 story building) rental with absolutely top snorkeling just a few steps away at a secluded beach and lava reefs, this is the...
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    About this property
    Turquoise Cove G301 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. Recently introduced to our exquisite...
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    Wailea, Maui 96753
    Rental Home - 5 Bathrooms, Sleeps 8
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    Sunny Surf E301 at Makena Surf1 / 58
    (7)Excellent
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 25, 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 May 23, 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
    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 the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. Recently introduced to our exquisite...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 6
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    Sun Splash C301 Wailea Beach Villas1 / 84
    (1)Excellent
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun Splash C301 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is ranked No. 3...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SeaGlass Villa 810 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Andaz Maui at Wailea Resort was...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    Coco Palms Pool Villa D101 at Wailea Beach Villas1 / 83
    (2)Very good
    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coco Palms Pool Villa D101 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 4 Bathrooms, Sleeps 6
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    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Air Conditioning
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Seashore Suite K507 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 2 Bathrooms, Sleeps 6
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    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Parking
    • Hot Tub
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 6
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    Wailea Sunset Estate1 / 67
    (13)Very good
    Studio, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Sunset Estate is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. Wailea Sunset Estate, one of our...
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    Wailea, Maui 96753
    Rental Home - 6 Bathrooms, Sleeps 10
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    Sandcastles Suite L509 Wailea Beach Villas1 / 88
    (6)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2016
    We booked through Tropical Villas Vacations. Yvonne was so great fielding all of our questions beforehand and providing us with an amazing about of information on the property...
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    About this property
    Sandcastles Suite L509 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016. The Wailea Beach Villas is ranked...
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 8
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    Mer Et Soleil K408 Wailea Beach Villas1 / 85
    (9)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Awards published on October 18, 2016. The Wailea Beach Villas is ranked No....
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    Wailea, Maui 96753
    Rental Home - 3 Bathrooms, Sleeps 8
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    Wailea Flight and Weather Info
    Airports nearby (1)
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    Kahului Airport
    14.3 miles from Wailea
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