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Wailea House Rentals

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    Travellers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    20 Matching Rentals in WaileaView all 276 rentals
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    One-of-a-Kind Maui Getaway1 / 28
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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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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    Regal Mandalay M511 Wailea Beach Villas1 / 50
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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, 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...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Wailea Sunset Bungalow1 / 40
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    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
    State of Hawaii Transient Accommodations Tax License #TA-*******-2528-01 County of Maui Short-Term Rental License #Hotel-Zoned 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...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    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 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
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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, 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'...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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, 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...
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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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    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, 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...
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    Location Information
    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rainbow Deluxe1 / 20
    (43)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 April 30, 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 October 9, 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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    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 The Wailea Beach Villas is ranked No. 3 in the Top 30 Best Resorts in Hawaii by Conde Nast Traveler's 2016 Readers' Choice Awards. The Wailea Beach Villas has also received TripAdvisor's prestigious Certificate of Excellence...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Turquoise Cove G301 at Makena Surf1 / 50
    (5)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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 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
    State of Hawaii Transient Accommodations Tax License #TA-*******-1504-01 Turquoise Cove G301/G302 at Makena Surf Resort is a sophisticated executive-style 4 bedroom (King, King, King, 2 Twins or King), 5 full-size bathroom double-size resort residence that sleeps up to eight guests in a prime top...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 5 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, voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best island...
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    Wailea, Maui 96753
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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
    • 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 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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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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, voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 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, 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'...
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    Location Information
    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical paradise is made even more magical with this luxury apartment villa. With a third-story location that has views of the Pacific and ample entertaining space both indoors and out, we’re certain your Maui vacation will be unforgettable. The open floor plan features tile throughout to keep...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 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 The Coco Palms Pool Villa at Wailea Beach Villas, also known as Villa D101, is a three bedroom, three and a half bath luxurious upscale residence with more than 3,200 square feet of living space, a virtual direct oceanfront...
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    Location Information
    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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