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Wailea House Rentals

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    $1,744 Average
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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    24 Matching Rentals in WaileaView all 241 rentals
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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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    Rainbow Deluxe1 / 20
    (41)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Wailea Sunset Bungalow1 / 46
    (13)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Sunny Surf E301 at Makena Surf1 / 58
    (7)Excellent
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    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
    <b>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.</b> Recently introduced to our...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Hot Tub
    • Sauna
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Ocean Views
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located across the street from the world renowned Wailea Beach, Ho'olei 81-1 is unequaled in splendor, elegance and convenience. Let this exceptional three bedroom, three and a half bath, two-level residence be your home away from home for your dream Hawaiian vacation. Every aspect of this...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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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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    Amenities & Details
    • Ocean Views
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2017
    We stayed here last week and had a wonderful week away. Its a newly renovated house and all of the bedrooms were a good size so suitable for a family or couples. The location...
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    About this property
    Welcome to our Cloud 9 Beach House. Local Maui couple Tamara and Steve Farwig invite you to stay with us in our lovely new home just a short walk to the beach. Keawakapu, a beautiful long white sand beach is a few minutes walk away or if you prefer, lounge poolside in the backyard or read a book...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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
    JULY 14th - 21st and 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...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Hot Tub
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>Orient Pacific Suite J505 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! 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...
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    Wailea, Maui 96753
    Holiday Rental House - 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
    <b>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.</b> Wailea Sunset Estate, one of...
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    Wailea, Maui 96753
    Holiday Rental House - 6 Bathrooms, Sleeps 10
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    Wailea Paradise H501 Wailea Beach Villas1 / 79
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>Wailea Paradise H501 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
    Holiday Rental House - 3 Bathrooms, Sleeps 4
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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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    Amenities & Details
    • 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 28 March 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 29 January 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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 18 April 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
    <b>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.</b> Recently introduced to our...
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    Wailea, Maui 96753
    Holiday Rental House - 5 Bathrooms, Sleeps 8
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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 17 January 2016
    Really cannot think of any negatives. The location of the villa was terrrfic; it was well appointed and staff was superb.
    Reviewed 15 August 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
    <b>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.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bathrooms, Sleeps 6
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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 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
    <b>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.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bathrooms, Sleeps 6
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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 25 April 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
    <b>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.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Holiday Rental House - 2 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 24 July 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. <b>Coral Gardens Estate at Makena Bay is located on Maui island, voted #1 best island in the WORLD by...
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    Wailea, Maui 96753
    Holiday Rental House - 4 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
    <b>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.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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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
    <b>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.</b> The Wailea Beach...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    Sandcastles Suite L509 Wailea Beach Villas1 / 88
    (6)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 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
    <b>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.</b> The Wailea Beach Villas is...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    Studio, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>Royal Ilima A201 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! 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
    Holiday Rental House - 4 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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    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>Sun Splash C301 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! 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
    Holiday Rental House - 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
    <b>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.</b> The Andaz Maui at Wailea...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bathrooms, Sleeps 6
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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
    <b>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.</b> The Wailea Beach Villas...
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    Wailea, Maui 96753
    Holiday Rental House - 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
    <b>Coco Palms Pool Villa D101 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! 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
    Holiday Rental House - 4 Bathrooms, Sleeps 6
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