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Vacation Rentals and Villas in Wailea, HI

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    $199
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    1 / 25
    5 of 5 stars (11) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3
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    1 / 8
    5 of 5 stars (17) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5
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    1 / 19
    3.5 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 / 19
    2 of 5 stars (1) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Internet Access
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    • Pet-friendly
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    • Elder access
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    About this property
    Beautifully furnished two bedroom Condo overlooking the Golf Course. The kitchen has been recently renovated. This unit offers many upgrades throughout and has many new furnishings. The bedrooms have all new furniture and the master bedroom features a beautiful wooden canopy bed. The accommodations... View all property information
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    Wailea, Maui 96753
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    $190
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Water Views
    • DVD Player
    • Satellite TV
    • Washer
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Live luxuriously while on vacation! Beautiful Hawaiian art, travertine floors, granite countertops, tall bath vanities, and elegant new furniture make this condo a place of comfort and serenity. The two bedrooms are private, each with an en suite bathroom. The master bedroom offers a California... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed March 19, 2015
    We spent a week in Maui for our son's first birthday. This condo was perfect for us, our little one, and my parents. The condo was clean and comfortable, beautifully furnished...
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    $225
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Secure Parking
    • Hot Tub
    • Private Outdoor...
    • Ocean Views
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Look no further! This is the condo for you! The Wailea Grand Champions is one of the premier vacation rental properties on the south side of Maui in the town of Wailea. A few minutes from the property are high-end five star resorts like the Four Seasons and the Grand Wailea. Also within minutes... View all property information
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    Wailea, Maui 96753
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    1 / 19
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Satellite TV
    • Waterfront
    • Watersports Nearby
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    DIRECT PANORAMIC OCEAN VIEWS. IF OTHERS DON'T SHOW IT, CHANCES ARE THEY DON'T HAVE IT. THE PHOTO ABOVE TAKEN FROM THE DINING ROOM WINDOW. Stunning Ocean Views from recently renovated, lower village condominium. Two Master Suites, one with a King bed, the other with a King and twin brd, also a... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed August 17, 2015
    WOW! Our 4th visit to Maui and we have finally found our vacation spot. Our stay at Wailea Ekahi Village 2A from August 2-6 was absolutely Amazing! The condo was immaculate...
    5 of 5 stars Reviewed June 15, 2015
    An excellent unit: very clean, great layout, loads of space, well stocked kitchen amenities, and nice view. Its well situated close to one of the quiet pools and a short walk to...
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    1 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • There Are Tennis...
    • Watersports Nearby
    • Internet Access
    • Waterfront
    • Satellite TV
    • DVD Player
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed July 13, 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
    5 of 5 stars Reviewed March 2, 2015
    This is a spacious condo with all the amenities you'd want for your vacation -- including a washer and dryer inside the condo and a full patio with BBQ. The setting is beautiful...
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    $267
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    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5
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    • Wi-Fi
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wailea Ekolu Village is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low density village consists of eighteen two-story buildings spread out over 18 acres of tropical landscaping and is conveniently located across... View all property information
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    Wailea, Maui 96753
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    $225
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    1 / 23
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Shared Outdoor Pool...
    • Wi-Fi
    • Waterfront
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    We are pleased to offer our new 1 bedroom,1 bath upper level condo for rental. It has been redecorated throughout, is newly furnished and equipped to high standards, is very comfortable and located in well maintained lush Ekahi Village. The condo is close to the best of everything we enjoy, 3+... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed September 15, 2014
    I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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    $190
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    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi Internet connection. Three flat screen TVs have been installed. Personal touches for your enjoyment and convenience. This unit is a 2,000-square-foot townhouse, occupying both the... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed March 29, 2015
    We were very pleased with our stay. Condo fully stocked. Beautiful views. Convenient location. Comfortable and roomy. Would stay here again.
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    $183
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    1 Bedroom, 2 Bathrooms, Sleeps 2
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    Overview
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    • Watersports Nearby
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • TV
    • There Are Tennis...
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Grand Champions Villas in Wailea are one of the fan favorite condominium properties in Wailea. Located minutes from five star resorts like the Four Seasons and Grand Wailea, this property is right where you want to be when vacationing on Maui. The Shops at Wailea, complete with high-end... View all property information
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    Wailea, Maui 96753
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    $240
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    1 / 35
    5 of 5 stars (2) Excellent
    1 Bedroom, 3 Bathrooms, Sleeps 4
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    • Housekeeping...
    • Ocean Views
    • Watersports Nearby
    • Wi-Fi
    • Mountain Views
    • Staffed Property
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    We recently remodeled our condo with all new upgraded tumbled travertine-style flooring, new window shades and new furniture. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3 of the cost and not have to purchase every meal in a resort hotel? You'll have a... View all property information
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    Wailea, Maui 96753
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    $1,200
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    1 / 14
    4.5 of 5 stars (6) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 3
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Ocean Views
    • DVD Player
    • Waterfront
    • Mountain Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    THIS IS OUR PERSONAL HOUSE AVAILABLE AUGUST 25 FOR 26 NIGHTS 1/2 PRICE! You can see & hear the ocean only 200 yards away. It's on this site as well with the heading Experience Old Hawaii.We are offering our personal house while away this Autumn. We will consider other dates as well. EXPERIENCE... View all property information
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    Wailea, Maui 96753
    From
    $1,400
    / Night
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    5 Bedrooms, 6 Bathrooms, Sleeps 12
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    • Dryer
    • Air Conditioning
    • Stereo System
    • Washer
    • Housekeeping...
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is a great opportunity to rent a private estate in Makena just a short stroll to some of the world's finest beaches. This villa is situated on a secluded estate on over two and one third acres of tropical landscapes, offers maximum privacy, security with breathtaking mountain, ocean and island... View all property information
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    Wailea, Maui 96753
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    $2,093
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    1 / 35
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5
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    Amenities & Details
    • Hot Tub
    • Water Views
    • Ocean Views
    • Mountain Views
    • Watersports Nearby
    • DVD Player
    • TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Experience the REAL 'Old Hawaii' in our private unattached HOUSE, NOT a noisy condo, ohana or part of a house. You will feel the ocean breeze, see it and clearly HEAR the ocean on this culdesac. From deck to ocean is about 200 yards in which you can walk to the beautiful Maluaka beach in about 1... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed May 15, 2014
    For me as an artist, staying at Sam and Rebecca's cottage, inspired a number of drawings, photographs and watercolors. My husband was able to disconnect from electronic media and...
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    $225
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
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    • Air Conditioning
    • Ocean Views
    • TV
    • Water Views
    • Watersports Nearby
    • Mountain Views
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Tastefully remodeled, this two bedroom, two bath condominium has many upgrades including a new contemporary kitchen with granite counter tops and stainless steel appliances. The master bathroom and guest bathroom were beautifully remodeled in 2015. Vaulted ceilings in the living room add to the... View all property information
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    Wailea, Maui 96753
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    $200
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    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Deck
    • Shared Outdoor Pool...
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This large 2 bedroom 2 bathroom villa has stunning views of the Old Blue Golf Course. Our spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. Our condo has has a great layout for two couples. Each couple has there own private... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed December 16, 2013
    My wife and I stayed in unit 29 at the Grande Champions Golf Villas for two weeks in December, 2013. The property manager Kathleen was fantastic to deal with and responded...
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    $140
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    1 / 27
    5 of 5 stars (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Tennis Court
    • Shared Outdoor Pool...
    • Hot Tub
    • Satellite TV
    • Water Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! Experience island life in our luxury, spacious, one bedroom. This rental is offered to you directly from a local couple intent on providing you with the ultimate vacation rental... View all property information
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    Wailea, Maui 96753
    From
    $440
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 2
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    • Hot Tub
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a... View all property information
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    Wailea, Maui 96753
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    $185
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    1 / 21
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Air Conditioning
    • Deck
    • Wi-Fi
    • Shared Outdoor Pool...
    • Hot Tub
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. This spacious 1148 square foot condo has a great layout for privacy. The large bedrooms are on opposite sides of the condo with their own private... View all property information
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    Wailea, Maui 96753
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    $275
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    1 / 22
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveler has booked this property
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Watersports Nearby
    • Hot Tub
    • Water Views
    • Mountain Views
    • TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This ground floor corner villa at Grand Champions Resort features three bedrooms, two baths, a fully equipped gourmet kitchen, and two lanais. Surrounded by the manicured fairways of Wailea's famed Blue Golf Course and the spectacular grounds of the Wailea Tennis Club, this quiet, well-managed... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed April 20, 2015
    The condo was spacious, clean and homely. They had everything we needed and the complex was well maintained. very close to Wailea town centre and 15 min walk to resort area. BBQ...
    4 of 5 stars Reviewed December 21, 2013
    We were a group of 6 adults and one toddler and we felt totally at home here and would definitely recommend this condo our friends. Set in an amazing area with world class...
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    $115
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    1 / 26
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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    Amenities & Details
    • Washer
    • Hot Tub
    • Stereo System
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed August 30, 2015
    This spacious studio was perfect for my needs. it was super comfortable and very very clean and there were little touches of extras like the chips and Karens bread in the...
    5 of 5 stars Reviewed May 3, 2015
    I loved this studio. It was very nice space with a deck. It has a stackable washer/dryer. The bed was super comfortable and owners were responsive to my needs. At the time I was...
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    $143
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    1 / 31
    5 of 5 stars (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Stereo System
    • TV
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool...
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a recently renovated luxury first floor condo in Wailea's premier Grand Champions Villas. Our home is unit #103 on the east side of the complex. Spend your vacation enjoying this 1 bedroom, 2 bath unit that provides ample space to spread out,... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed April 23, 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 stars Reviewed September 10, 2013
    I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
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    $250
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    1 / 16
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Notes from the Owner: Wailea Elua Village #801 is located in the center of the Elua Village just across from the small pool and Jacuzzi area and just steps to the paddle court. Enjoy ocean views as well as secluded garden views from this quiet ground floor, two bedroom, two bath unit. The lanai... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed August 29, 2014
    This was a fantastic stay. The accommodation was booked through mauivacationadvisors.com. The agency represents many properties. They were a huge help, offering suggestions...
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    $400
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    1 / 19
    5 of 5 stars (40) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Shared Outdoor Pool...
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Water Views
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wow ! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui Wailea, Ekahi Village condo (28D). Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than four minutes.When you... View all property information
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    Wailea, Maui 96753 9532
    5 of 5 stars Reviewed May 30, 2015
    This is a beautiful condo in Wailea. The location is a perfect point to easily access the convenience of Keihi and the beauty and elegance of Wailea. The condo is great for two...
    5 of 5 stars Reviewed April 10, 2015
    My family stayed at Sharon and Lynn's condo for 3 weeks in January. The place and the owners were fabulous. The condo was very clean and organized--with everything you could...
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    $290
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    1 / 10
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    Overview Reviews (1)
    Amenities & Details
    • Washer
    • Dryer
    • Shared Outdoor Pool...
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Please visit our personal website listed below to view comments from many of our previous guests!!!! We have photographed our guestbook so you can see for yourself how much our past guests have loved our condo. Click on the Guestbook tab of our personal website.Aloha!! Welcome to our home away from... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed January 15, 2015
    Three of us (2 adults and 16 yo) stayed in this condo for 2 weeks (Dec 2014) and had a relaxing and comfortable stay on our adventure filled vacation. The location of the condo is...
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    $250
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    1 / 10
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (6) Make Inquiry
    Overview Reviews (6)
    Amenities & Details
    • Washer
    • Stereo System
    • Air Conditioning
    • Water Views
    • Internet Access
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Please visit our personal website listed below to view our guestbook with comments from many of our previous happy guests!!!! We have photographed our guestbook so you can see for yourself how much our past guests have loved our condo. Click on the Guestbook tab of our personal website .Welcome to... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed May 26, 2015
    We really enjoyed our stay in Wailea! Great location, with a 10 minute walk to the beach. The condo was very comfortable, with all of the amenities of home. The bedrooms were...
    5 of 5 stars Reviewed February 17, 2015
    Great Condo. Location was terrific. Jan was fantastic to work with, even transferred our deposit to the following year,due to us having to cancel!
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    $750
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    1 / 30
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (18)
    Amenities & Details
    • DVD Player
    • Washer
    • Water Views
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Wailea, Maui 96753
    From
    $338
    / Night
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    About this condo: Wailea Elua Village #106 is a second floor, two bedroom-two bath, oceanview condo with a large lanai complete with a sun shade screen. It has a king bed in the master bedroom and a queen bed in the guest bedroom. This unit can be rented as a one bedroom during non peak periods.... View all property information
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    Wailea, Maui 96753
    From
    $495
    / Night
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    1 / 46
    5 of 5 stars (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (9) Make Inquiry
    Overview Reviews (9)
    Amenities & Details
    • Waterfront
    • Water Views
    • DVD Player
    • Hot Tub
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    2-5 Bedroom, on the sand in front of the Fairmont Kea Lani in Wailea / Makena Maui, Hawaii. Features: Beach Front - On the Sand! Snorkeling. Central Air conditioning We have correct HOTEL ZONING for Maui vacation rentals Sleeps 6 Two elevators By Owner Beachfront Pool and Spa On the Wailea... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed November 30, 2014
    The highlight of the stay for me was the back lanai. It was large enough for me to do my yoga in the morning and it had a wonderful breeze and an incredible view! The four of...
    5 of 5 stars Reviewed July 25, 2014
    Beautiful ocean view from balcony, living room and kitchen. My family loved unit # 306. Condo was better than photos. Very comfortable for a family of 5. Beds were comfortable...
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    $3,500
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    1 / 35
    5 of 5 stars (2) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8
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    • Satellite TV
    • Stereo System
    • Dishwasher
    • Hairdryer
    • Dryer
    • Grill
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Designed by world-renowned architect Tan Hock Beng, Hale Kumulani is a magnificent home built around a grass courtyard. Boundaries between indoors and out are blurred, with walkways connecting bedroom suites to the main living areas. Located directly across the street from the exquisite white sand... View all property information
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    Wailea, Maui
    From
    $995
    / Night
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    1 / 32
    5 of 5 stars (5) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (5) Make Inquiry
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Water Views
    • Mountain Views
    • Internet Access
    • Satellite TV
    • Children's Pool
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    'Wailea Beach Villas is the #1 Specialty Lodging in Wailea' - Trip Advisor 'Wailea Beach Villas is one of the top 100 hotels in the USA' - Conde Nast Readers Choice Award The Wailea Orchid is an amazing 3 bedroom / 3 full baths penthouse villa located in the prestigious Wailea Beach Villas.... View all property information
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    Wailea, Maui 96753
    From
    $395
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    1 / 23
    5 of 5 stars (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Reviews (17) Make Inquiry
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    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Stereo System
    • DVD Player
    • Shared Outdoor Pool...
    • Water Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to our home! Enjoy the fantastic ocean views and luxury of our home in Wailea Elua Village - a gated, 24 acre, oceanfront community. Our home is perfectly situated in the center of the Wailea Elua Village property (Unit #701). We are 150 yards from Ulua Beach -- just a 90 second walk to... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed August 6, 2014
    We stayed for five days in July with 2 children and 2 adults. The unit was exactly as advertised and had everything and more that we needed during our stay. The view from lanai...
    5 of 5 stars Reviewed April 27, 2014
    Stayed her with our 18 yr old daughter for a week -- everything was perfect. Kitchen couldn't have been better equipped, lanai as advertised was huge. Complex was quiet, well...
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    $159
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    1 / 16
    4 of 5 stars (9) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Grill
    • DVD Player
    • Stereo System
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wailea Ekahi Village is a beautifully terraced property located at the entrance to the resort community of Wailea. This relaxing low-density property consists of 54 two-story buildings spread out over thirty-four acres of immaculate tropical landscaping. Keawakapu Beach fronting the property is... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed February 15, 2013
    We stayed at 24B in Ekahi in October and had a great stay. It is about a 200 yard walk from the condo down to what I would have to say is one of the best beaches on Maui. We...
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    $225
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
    Overview Make Inquiry
    Overview
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    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Staffed Property
    • Water Views
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Beautiful Wailea - 1 Block from The Shops At Wailea, Several Restaurants, Beaches, Four Seasons Hotel, Tennis Across the Street, Golf right below Condo Bus Stop and close proximity to many places. Unique Condo fully remodeled with African Mahogany wood throughout, Granite counters in kitchen, Water... View all property information
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    Wailea, Maui 96753
    From
    $1,795
    / Night
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    1 / 34
    3 Bedrooms, 4 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Dishwasher
    • DVD Player
    • Dryer
    • Stereo System
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ocean Bliss is a stunning beachfront estate that provides the best of all worlds...Privacy and ocean access as the house borders South Maui's Polo Beach with it's golden sands and shallow swimming area on one side of the villa and a dramatic lava rock beach on the other side. The vistas of the sea... View all property information
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    Wailea, Maui
    From
    $115
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    1 / 24
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Stereo System
    • Satellite TV
    • Washer
    • Shared Outdoor Pool...
    • Gym
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Unit 181 is located in the heart of the beautiful and serene Grand Champions Villas. On the edge of the Wailea Blue Golf course, this condo is great for the golfing couple looking for a tropical getaway. Large green belts, manicured grounds and wide golf course fairways abound. Nearby shopping,... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed May 26, 2015
    This is a great condo. We were little unsure because it had no reviews but we are very happy that we booked it. It is renovated, with 2 bathrooms (each has a toilette as well...
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    $255
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    4.5 of 5 stars (27) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Stereo System
    • DVD Player
    • Watersports Nearby
    • Air Conditioning
    • Water Views
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    20B is a delightful, spacious condo in the Lower Village of Ekahi, at the bottom of the hill and closest to the beach. In fact it's only a 2 minute walk to world renowned Keawakapu Beach! And because the walk path is nearly level, you avoid hiking up the hill after being at the beach all day --... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed January 24, 2015
    We have stayed at Wailea Ekahi many times over the past 20 years and consider it the best value on the island. We usually have stayed along the large common green that slopes...
    5 of 5 stars Reviewed December 29, 2014
    We stayed for two weeks in this lovely unit in the Wailea Ekahi complex. The complex is set in the midst of a well tended and spectacular garden setting. We have stayed in the...
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    $325
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    1 / 10
    4 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Amenities & Details
    • Ceiling Fans
    • Shared Outdoor Pool...
    • Grill
    • Air Conditioning
    • Dishwasher
    • Microwave
    • TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    A rare find! This 3 bedroom 3 bath multi level condominium apartment is like a private home! From the entry you can step up to the open living area with a ocean view lanai. The spacious living area can easily accommodate a family get together with the entertainment area and comfortable dining... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed July 8, 2015
    We got married in Maui and rented this condo for my husband, his 2 grown kids and my 3 grown kids. The place is 3 levels. You walk in the front door. There are 2 bedrooms...
    3 of 5 stars Reviewed February 13, 2015
    Spacious condo located close to one of the smaller beaches. Pleasant but somewhat dated. The upkeep of smaller details could be improved/made to function.Could do with a solid...
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    $150
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    1 / 24
    4 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (6)
    Amenities & Details
    • Gym
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    • Water Views
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious living room opens to the Lanai, where there is ample space for stretching out and relaxing in the sun, barbecuing on your own private grill, or admiring the tropical grounds of The Palms at Wailea.... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed February 15, 2015
    This is a terrific location for a visit to South Maui. We used the whale watch rafts from the Kehei ramp. Close to Safeway, beaches with full service and beach parking. Loved...
    4 of 5 stars Reviewed August 2, 2014
    We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
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    $750
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • DVD Player
    • Water Views
    • Children's Pool
    • Air Conditioning
    • Sauna
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    PLEASE NOTE: OUR CALENDAR APPEARS OPEN BECAUSE WE OWN 5 HOMES AT THE HO'OLEI RESORT. IN MOST CASES, I DO HAVE A HOME AVAILABLE! Come enjoy our Luxury Residence in what we call our Executive Model! This home is the Hibiscus Model, which is the largest home at Ho'olei (3,301 sq. ft. and a 686 sq.... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed August 12, 2013
    We stayed in unit 24-1. The accommodations were first class. There aren't enough words to describe the luxury. We took our adult kids and their children. There was lots of...
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    $450
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    1 / 41
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (19) Make Inquiry
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    Amenities & Details
    • TV
    • Ocean Views
    • Water Views
    • Mountain Views
    • Wi-Fi
    • Ping Pong Table
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled in a quiet lower village setting right on the green belt, our Maui home has recently undergone a complete professional remodel. The ceiling has a real Hawaiian feel with beams and matting, we've opened the kitchen to the living room and created two master suites with private bathrooms. The... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed June 4, 2015
    Fabulous location, quiet, short walk to beach, and too close to the best ice cream ever, Lapperts. Extremely well equipped unit even down to stored water and full emergency...
    5 of 5 stars Reviewed November 22, 2014
    The Ekahi Village 11f has been beautifully updated; with lovely finishings, an extraordinarily well stocked kitchen and views from the shady Lani to enchant you, it is hard to...
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    $100
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    1 / 7
    5 of 5 stars (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Stereo System
    • Air Conditioning
    • Hot Tub
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SEPTEMBER AVAILABILITY: Arrive Aug. 30th depart Sept. 8th, OR Arrive Sept. 13th depart Sept. 23rd OR Arrive Sept. 27th depart Oct. 3rd. $100/night plus tax (13.416%) and cleaning $75. FREE TELEPHONE TO THE MAINLAND AND CANADA. This great one bedroom condo is offered as your home during your... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed January 25, 2014
    My partner and I came to Maui to run the Maui Oceanfront Marathon. We had booked a room at the Marriott for which the marathon had a room block. However, because we wanted to...
    5 of 5 stars Reviewed February 3, 2013
    Three of us (wife, toddler girl and myself) rented this place in early January. The condo is just the right size for us. We love the location. It's in an upscale area of Maui...
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    $199
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    1 / 19
    4.5 of 5 stars (17) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Stereo System
    • Hot Tub
    • Watersports Nearby
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Relax in the luxury and convenience of being in a world class resort, but enjoy the privacy and beauty of our fabulous 2 bd/2ba ground floor 'home away from home' that fronts the 7th Fairway of the famed Wailea Blue Course. Our spacious 1100 sq ft. unit has a tropical decor with world-class art... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed May 3, 2015
    Stayed here with my husband, toddler and my parents - and it was perfect. The location is right by beaches, shops and restaurants. Also, there are boogie boards, snorkeling...
    5 of 5 stars Reviewed November 7, 2011
    The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea, the...
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    $595
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    1 / 24
    5 of 5 stars (21) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Waterfront
    • Shared Tennis Court
    • Air Conditioning
    • Watersports Nearby
    • Hot Tub
    • Staffed Property
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located 'down in front' on the water at Wailea Elua Village, this Second Floor AIR CONDITIONED Condominium has received a complete Custom-Designed Interior Renovation. Everything has been updated - flooring, furniture, artwork, lighting, and fixtures - including a fully upgraded kitchen with... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed September 24, 2013
    This is the condo to rent! I spent a long time looking at condos on various websites and I feel so fortunate to have found this condo! The owners are easy to work with and...
    5 of 5 stars Reviewed August 4, 2011
    This was a very beautiful, upscale condo with a wonderful, well-stocked kitchen; there was a grill so we had 3 meals in and enjoyed dining on the lanai -- gorgeous view. It was...
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    $400
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    1 / 18
    5 of 5 stars (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3
    Overview Reviews (6) Make Inquiry
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    Amenities & Details
    • Satellite TV
    • Deck
    • Water Views
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Aloha! 29F is located in the lower village and has arguably the best view in Ekahi Village. This professionally remodeled unit comes with all the amenities of a five star hotel, yet all the comforts of home. Ocean front gourmet kitchen, lanai and living room. Pool and beach are just steps away.... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed October 10, 2013
    My husband and I stayed at Unit 29F Oct. 1 - Oct. 6, 2013. It was our first trip to Maui and our first experience renting a condo vs. staying at a resort. We definitely made the...
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    $395
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    1 / 29
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Amenities & Details
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Private Outdoor...
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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,... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars 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...
    5 of 5 stars Reviewed July 8, 2014
    The wife and I and are 3 children (9, 9 and 3) stayed here for 8 nights! Looked at many homes in Maui and man did I nail it with this one! Perfect location, perfect owners...
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    From
    $750
    / Night
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    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Overview
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Mountain Views
    • Children's Pool
    • Hot Tub
    • Water Views
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    This spacious, professionally decorated town home has all the comforts you expect from a five star experience. The world renowned Grand Wailea resort located across the street, offers a world class spa, shopping and beach. Whether you group has many children, adults or seniors, this home is... View all property information
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    Location Information
    Wailea, Maui 96753
    From
    $355
    / Night
    View Details
    1 / 23
    5 of 5 stars (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (10) Make Inquiry
    Overview Reviews (10)
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Gym
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful three bedrooms, two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated in the fall of 2010 with granite throughout, stainless steel appliances, new carpet, paint and furniture. The living area is a large open floor plan with ceiling fans and... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed October 9, 2014
    My friends an i find the Grand Champions condos to be quiet an peaceful. It's close to three great golf courses and several good restaurants. We live in Honolulu, where we have...
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    Wailea Vacation Rentals

    Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

    A Wailea Vacation

    No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

    Family-Friendly Wailea

    From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.