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Wailea House Rentals

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    Wailea is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    29 Matching Rentals in WaileaView all 334 rentals
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    One-of-a-Kind Maui Getaway!1 / 28
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Wailea Sunset Bungalow1 / 42
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    • 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 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
    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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • 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 Pool1 / 62
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Ocean Views
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Washer
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful two level residential home located in South Kihei, Maui. The 3 larger bedrooms have their own private bathrooms. The 2 smaller bedrooms share the 4th guest bathroom. 2 living rooms. 2 car garage. This is South Kihei's newest vacation rental offering. Fully furnished with all the...
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    Wailea, Maui 96753
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    • 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Coral Gardens at Makena Bay1 / 50
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    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
    State of Hawaii Transient Accommodations Tax License #TA-*******-0368-01 County of Maui Short-Term Rental License #STKM 2013/0011 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:...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wailea Sunset Estate1 / 50
    (13)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-4976-01 County of Maui Short-Term Rental License #Hotel-Zoned Wailea Sunset Estate 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,...
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    Wailea, Maui 96753
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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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    • 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Washer
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-2464-04 Wailea Seashore Suite K507 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Several beautiful white sand...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-8592-01 County of Maui Short-Term Rental License #Hotel-Zoned Resort SeaGlass Villa 810 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...
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    Wailea, Maui 96753
    Holiday Rental House - 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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    • 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 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
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    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
    State of Hawaii Transient Accommodations Tax License #TA-*******-6208-01 Regal Mandalay M511 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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    Rainbow Deluxe1 / 20
    (43)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Internet Access
    • Hot Tub
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2018
    For anyone needing a secluded place with AMAZING owners, please PLEASE check this place out. Joe and MaryAnne are so accommodating, welcoming, and their home is spectacular...
    Reviewed 10 October 2017
    My husband and I found the Rainbow Deluxe cottage after another booking we had made (with someone else) fell through. It really was a blessing in disguise though, because we...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Turquoise Cove G301 at Makena Surf1 / 46
    (5)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Hot Tub
    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
    State of Hawaii Transient Accommodations Tax License #TA-*******-1504-01 Turquoise Cove G301/G302 at Makena Surf Resort 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...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 5 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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    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • 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-*******-6368-02 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Located on the ground, second and third floors are our one-bedroom two-bathroom partial ocean view condos. It’s easy to relax with views of beautifully landscaped gardens and the ocean channels between Maui, Molokini, Kahoolawe, and Lanai. Enjoy a private furnished lanai, air conditioning, a full...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Island décor and tropical tones say aloha in this 884sf suite with furnished lanai flowing onto beautiful lawns. Homey touches include ceiling fans, air conditioning, WiFi, upgraded full kitchen with dishwasher, dining area, flat screens, tile flooring and washer/dryer. Sleeps 4 in 1 Queen & 1 Sofa...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy views of the West Maui Mountains and majestic Haleakala from your standard one bedroom condo. These comfortable accommodations include spacious rooms with air conditioning and a private furnished lanai to help you unwind on your vacation. Each unit is individually and uniquely furnished with...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the ground, second and third floors are our one-bedroom two-bathroom partial ocean view condos. It’s easy to relax with views of beautifully landscaped gardens and the ocean channels between Maui, Molokini, Kahoolawe, and Lanai. Enjoy a private furnished lanai, air conditioning, a full...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy views of the West Maui Mountains and majestic Haleakala from your standard one bedroom condo. These comfortable accommodations include spacious rooms with air conditioning and a private furnished lanai to help you unwind on your vacation. Each unit is individually and uniquely furnished with...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Each unique two-bedroom two-bathroom partial ocean view condo is uniquely designed and located on the fourth floor. Enjoy views of landscaped gardens and the channels between Maui, Molokini, Kahoolawe, and Lanai from your private furnished lanai. Amenities include air conditioning, a full kitchen,...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    PRIMO OCEAN VIEW / SOUND JUST STEPS TO MALUAKA BEACH MAKENA HOUSE South Maui HI1 / 28
    (6)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
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    • Mountain Views
    • Grill
    • Ocean Views
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At our house you can see and HEAR the beach/ocean, in a few steps be in the ocean, shower privately outdoors, enjoy fruit trees and grill with wood or charcoal. You have free use of bicycles, SUP boards, kayaks, snorkel gear, fishing gear, boogie boards, yoga mats and even DVR shows/sports :) We...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the ground, second and third floors are our one-bedroom two-bathroom partial ocean view condos. It’s easy to relax with views of beautifully landscaped gardens and the ocean channels between Maui, Molokini, Kahoolawe, and Lanai. Enjoy a private furnished lanai, air conditioning, a full...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Internet Access
    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the ground, second and third floors are our one-bedroom two-bathroom partial ocean view condos. It’s easy to relax with views of beautifully landscaped gardens and the ocean channels between Maui, Molokini, Kahoolawe, and Lanai. Enjoy a private furnished lanai, air conditioning, a full...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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