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Wailea Vacation Rentals

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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    19 Matching Rentals in WaileaView all 321 rentals
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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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    Regal Mandalay M511 Wailea Beach Villas1 / 50
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Sandy Surf K508 at Wailea Beach Villas1 / 50
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-4016-01 Sandy Surf K508 is located on Maui island, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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 6 days ago
    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 4 weeks ago
    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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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-2464-01 Royal Ilima A201 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
    Rental Home - 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 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
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sun Splash C301 Wailea Beach Villas1 / 50
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-8688-01 Sun Splash C301 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
    Rental Home - 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 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
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Location Information
    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Castaway Cove C201 at Wailea Beach Villas1 / 50
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • 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
    State of Hawaii Transient Accommodations Tax License #TA-*******-0848-01 Castaway Cove C201 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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Sandcastles Suite L509 Wailea Beach Villas1 / 50
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    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
    State of Hawaii Transient Accommodations Tax License #TA-*******-2464-03 Sandcastles Suite L509 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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 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
    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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Golden Mandarin D102 Wailea Beach Villas1 / 50
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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
    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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Aqua Lani J305 Wailea Beach Villas1 / 50
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bali Hai Pool Villa F102 at Wailea Beach Villas1 / 50
    (4)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-1360-01 Bali Hai Pool Villa F102 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
    Rental Home - 3 Bedrooms, 4 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coco Palms Pool Villa D101 at Wailea Beach Villas1 / 50
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    • Hot Tub
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-1360-05 Coco Palms Pool Villa D101 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...
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    Wailea, Maui 96753
    Rental Home - 3 Bedrooms, 4 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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    Amenities & Details
    • 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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    Location Information
    Wailea, Maui 96753
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wailea Flight and Weather Info
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    Kahului Airport
    14.3 miles from Wailea
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