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Vacation Rentals and Villas in Wailea, HI

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    All 214 Rentals in Wailea
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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $190
    / Night
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    1 / 16
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (5) Make Inquiry
    From
    $285
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    1 / 24
    4 of 5 stars (3) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Inquiry
    From
    $210
    / Night
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    1 / 16
    4 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (3) Make Inquiry
    From
    $1,288
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    1 / 45
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Mountain Views
    • Sauna
    • Satellite TV
    • Water Views
    • Children's Pool
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Modern Maui, our ocean view villa located in the heart of beautiful Wailea, combines all the best elements of a premium vacation home: Location, space, amenities and Grand Wailea Resort access. EXCLUSIVE GRAND WAILEA RESORT BENEFITS FOR OUR GUESTS: * On-demand, free transportation to and from... View all property information
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    Wailea, Maui 96753
    From
    $220
    / Night
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    1 / 16
    5 of 5 stars (1) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Gym
    • Grill
    • Satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Refrigerator
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Great Fall 2015 Rates - Please Ask! Wailea Ekahi 45B is a ground floor, 1 bedroom/2 bathroom garden view condo located in the upper village. The bedroom is furnished with a king size bed, air conditioning and new flat screen TV. Wailea Ekahi Village boasts 34 tropical landscaped acres bordering one... View all property information
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    Wailea, Maui 96753
    From
    $425
    / Night
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    1 / 27
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Gym
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Special Fall 2015 Rates ! Please ask. Wailea Ekahi Village 53C is a fully renovated, 2 bedroom/2.5 bath townhouse with ocean views from the upstairs bedrooms and private downstairs lanai. It has 1575 sq. feet of living space. The master bedroom suite offers a king bed, sitting area, TV, DVD, a/c... View all property information
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    Wailea, Maui 96753
    From
    $810
    / Night
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    1 / 19
    5 of 5 stars (7) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool...
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named with vaulted ceiling, HD TV, DVD, wireless internet and formal dining area. Tropical blue and turquoise colors convey a serene ambiance comparable to the pristine... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed December 28, 2014
    Definitely a great condo. Ho'oeli isn't a wonderful property. Pool is outstanding. Massage poolside-definitely get one! Mercedes is amazing. Condo has comfy beds, elevator if...
    5 of 5 stars Reviewed July 23, 2014
    Our vacation rental was clean, spacious, quiet and most importantly, had great views. If you are looking for a great family rental on your vacation, I highly recommend Ho'Olei!
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    From
    $375
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    1 / 21
    5 of 5 stars (3) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Gym
    • Shared Outdoor Pool...
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful ocean views, swimming and snorkeling from the property, and a fully refurbished condominium awaits you at our Elua Village 2011. This one bedroom two bath is tiled throughout, has central air conditioning along with ceiling fans. The living area offers flat screen TV, high speed wireless... View all property information
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    Wailea, Maui 96753
    From
    $710
    / Night
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    1 / 22
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Stereo System
    • Gym
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Special Fall 2015 Rates. Please ask ! Relax and spread out in more than 3300 interior feet of custom home with designer furnishings. The tropically furnished living area with vaulted ceiling offers HD TV, DVD, IPod dock, and wireless internet, all in an intimate yet spacious room. The gourmet... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed March 1, 2015
    We rented this Villa to vacation with our adult children, son, daughter and son in law for a week in February. It was exactly as I pictured it online and was lovely, very clean (I...
    4 of 5 stars Reviewed January 26, 2014
    Had a great stay at 24-6 Ho'olei and on Maui. The condo was very large, clean, and well appointed, everything we needed for a base of our stay. A 5 minute walk to the beach...
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    From
    $275
    / Night
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    1 / 22
    4.5 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Reviews (3) Make Inquiry
    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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    Location Information
    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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    From
    $210
    / Night
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    1 / 24
    4 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Linens Provided
    • Grill
    • Shared Outdoor Pool...
    • Parking
    • Washer
    • Refrigerator
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    (IMPORTANT CONSTRUCTION NOTICE: Wailea Community Association has approved a large scale project that is currently going on near Wailea Ekolu Village. The project includes road resurfacing and a new building that is expected to be near the Wailea Blue course clubhouse. Also - Across the 4 lane... View all property information
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    Location Information
    Wailea, Maui 96753
    4 of 5 stars Reviewed December 28, 2014
    I had some reservations when I booked this unit in May since the advertised photos showed what seemed like a “too-pretty-to-be-true” panoramic ocean view. I’ve heard so many...
    4 of 5 stars Reviewed November 11, 2014
    I was a little worried to about renting this condo as it had no reviews, but it was better than I expected. The condo is clean, very nicely decorated and has a great covered...
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    From
    $225
    / Night
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    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • 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
    $338
    / Night
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • 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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    Location Information
    Wailea, Maui 96753
    From
    $285
    / Night
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    1 / 16
    5 of 5 stars (1) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Grill
    • Stereo System
    • Wi-Fi
    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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    Location Information
    Wailea, Maui 96753
    From
    $440
    / Night
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Grill
    • Hot Tub
    • Wi-Fi
    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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    Location Information
    Wailea, Maui 96753
    From
    $342
    / Night
    View Details
    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • DVD Player
    • Stereo System
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    NEW TO OUR PROGRAM! UPDATES & IMPROVEMENTS ... Wailea Elua Village #2010 is located on one of the buildings corners, giving you ocean views and property from the master lanai and the main lanai which may also be accessed via the guest bedroom. Recently added to the condo area large new flat screen... View all property information
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    Wailea, Maui 96753
    From
    $115
    / Night
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    1 / 26
    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (10) Make Inquiry
    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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    Location Information
    Wailea, Maui 96753
    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...
    5 of 5 stars Reviewed June 13, 2013
    My boyfriend and I stayed at Wailea Grand Champions for a couple of nights and we loved it. The property is beautifully maintained and it is located very close to several great...
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    From
    $810
    / Night
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    1 / 19
    5 of 5 stars (6) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (6) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    • Stereo System
    • Deck
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Relax in this spectacular three bedroom deluxe accommodation. Beautifully decorated, many exquisite art pieces and special touches create a warm inviting atmosphere. The living room features state of the art entertainment center with 50' HD TV, DVD, Ipod dock, high speed and wireless internet. The... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed August 12, 2011
    We stayed for a week as a young family of four. The location in the complex was ideal as we could easily walk to *and* see the pool--many units offer one but not the other. This...
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    From
    $355
    / Night
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    1 / 19
    3 of 5 stars (1) Average
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Waterfront
    • Refrigerator
    • Air Conditioning
    • Internet Access
    • Gym
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Wailea Ekahi 14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home ! You will feel like you are on top of the world as you look out from the second floor onto the Greenbelt and over the blue Pacific Ocean. The... View all property information
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    Wailea, Maui 96753
    From
    $220
    / Night
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    1 / 18
    4.5 of 5 stars (3) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    • Gym
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This ground floor, Wailea Ekahi condominium has an ocean view. There is a king bed in the master bedroom and queen sofa sleeper in the living room. Air conditioning in both the bedroom and living room, ceiling fans throughout, portable stereo with CD player, 2 TV’s and DVD player. There are linens,... View all property information
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    Location Information
    Wailea, Maui 96753
    4 of 5 stars Reviewed May 7, 2014
    This was our first trip to Maui so we weren't quite sure what to expect. All I can say is that we loved it! The condo worked out brilliantly with lots of space; very well equipped...
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    From
    $750
    / Night
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    1 / 25
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Wailea, Maui 96753
    From
    $315
    / Night
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    1 / 20
    4.5 of 5 stars (2) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Grill
    • Wi-Fi
    • Gym
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This condominium home has been beautifully upgraded throughout and boasts a newly remodeled kitchen, dining room and living room. Summer 2014 new carpet was added throughout and new living room furniture greets you. The comfortable bedroom has a king bed and en-suite bathroom. There is free... View all property information
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    Wailea, Maui 96753
    From
    $315
    / Night
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    1 / 16
    5 of 5 stars (4) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Grill
    • Shared Outdoor Pool...
    • Wi-Fi
    • Gym
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Please ask for our Fall 2015 Specials! Come enjoy condominium living at its finest at Wailea Ekahi 17D. Located in the heart of Wailea, Maui - Wailea Ekahi 17D is a one bedroom, two bath deluxe condominium on the 2nd floor with panoramic ocean views. Enjoy fabulous ocean and outer island views from... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed October 25, 2014
    Stayed at Wailea Ekahi 17D.Everything about this condo was PERFECT. It was well kept; pristine....the view was breathtaking. This whole community was WONDERFUL. Pool area and...
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    $250
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    1 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool...
    • Internet Access
    • Grill
    • Gym
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Please ask for our Fall 2015 Special Rates!! This beautiful condo has been upgraded throughout. It has a king bed, air conditioning in the living room, bedroom and ceiling fans throughout. The extended lanai runs the full length of the condo. Conveniently located, this condo is just a short walk to... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed July 16, 2014
    Very well appointed unit and beautifully maintained grounds. Went over for my niece's wedding. We had a pre-wedding function with 15 people and everything had we needed...
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    $200
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    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Inquiry
    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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    From
    $405
    / Night
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    1 / 19
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Refrigerator
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Gym
    • Waterfront
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Please ask for our Fall 2015 rates! Wailea Ekahi 27B offers Ocean views from the upstairs master bedroom Living area and Lanai. The master bedroom has a king bed, ocean view and en-suite bath. The guest bedroom has a new Queen bed and beautiful garden view. Both bedrooms have air conditioning and... View all property information
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    Wailea, Maui 96753
    From
    $365
    / Night
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Satellite TV
    • Grill
    • Gym
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Special Fall 2015 Pricing - Please Ask. Wailea Ekahi Village 35B is where you want to be. It is the paradise you have been looking for. Walking through the landscaped grounds, you are surrounded by beautiful orchids, ginger, bougainvillea and hibiscus flowers. Both bedrooms are furnished with king... View all property information
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    Wailea, Maui 96753
    From
    $495
    / Night
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    1 / 34
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Water Views
    • Hot Tub
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Wailea, Maui 96753
    From
    $265
    / Night
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    1 / 16
    5 of 5 stars (1) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool...
    • Gym
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Special Fall 2015 Rates - Please inquire. This beautifully renovated condominium offers ocean views and greenbelt views. It has a king bed, queen sofa sleeper, air conditioning in the living room and bedroom, ceiling fans throughout and an extended lanai that runs the length of the unit. Wailea... View all property information
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    Wailea, Maui 96753
    From
    $1,850
    / Night
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    1 / 78
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Stereo System
    • Grill
    • Refrigerator
    • Internet Access
    • Dishwasher
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
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    Wailea, Maui 96753
    From
    $306
    / Night
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    1 / 18
    5 of 5 stars (32) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 3
    Overview Reviews (32) Make Inquiry
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Watersports Nearby
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Staffed Property
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    GREAT LOCATION AND VIEW! Completely remodelled, refurnished & professionally decorated. A true 'Paradise in Maui' awaits you in our beautiful, ocean view, upper floor, 1 bedroom, 2 bath condo (1160 sf) in the Lower Village of Wailea's spectacular ocean front Ekahi Village. The condo can... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed June 28, 2015
    You will not be disappointed if you rent this condo! It has close proximity to the beach and pool, a great view and privacy. Maps of Ekahi can be deceptive as some of the...
    5 of 5 stars Reviewed June 15, 2015
    This past September I stayed for my third time in this lovely condo. This time I came alone which was just lovely as I knew what to expect and could just relax. This condo is a...
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    $225
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    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • DVD Player
    • Gym
    • Wi-Fi
    • Satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Please ask us about our Summer and Fall 2015 Specials. Grand Champions 186 is located on the second floor and overlooks one of the 2 pools on property. Featuring a modern Hawaiian theme throughout. The living room has a large High Definition TV with DVD, high speed and wireless internet, comfy... View all property information
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    Wailea, Maui 96753
    From
    $35,000
    / Week
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    1 / 9
    7 Bedrooms / 6 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Refrigerator
    • Water Views
    • DVD Player
    • Grill
    • Stove
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Sea Pearl Estate is a regal Hawaiian vacation rental located near Wailea in Maui. Set upon approximately 6,500 square feet of island refinement, all guests are sure to enjoy Maui at her best. This Maui vacation estate in Wailea has the ability to comfortably accommodate up to 14 happy guests... View all property information
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    Location Information
    Wailea, Maui 96761
    From
    $1,095
    / Night
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    1 / 80
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Parking
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    an glass cooking range, juicer, two coffee makers with timers, integrated sub-zero wine/refrigerator with dual-climate wine storage and two sub-zero refrigerator/freezers with ice maker, various condiments and cooking supplies including sugar packets, answering machine, wool berber carpets, full... View all property information
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    Wailea, Maui 96753
    From
    $150
    / Night
    Payment Protection
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    1 / 20
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • 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
    From
    $140
    / Night
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    1 / 23
    5 of 5 stars (19) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (19) Make Inquiry
    Amenities & Details
    • Washer
    • Hot Tub
    • Stereo System
    • DVD Player
    • Dryer
    • TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Great Deal for a luxury rental in wailea. Contact us soon BOOK 5 OR MORE NIGHTS, $140/NT + $90 CLEANING FEE + TAX NEXT AVAILABLE - : JUL 24-29, 5 NTS, $120/NT + $90 CLNG FEE + 13.42% TAX AUG 13-16, 3 NTS, $120/NT. + 13.42% Hi. Tax + $90 cleaning fee AUG 25-SEP 05, 11 NTS, $140/NT '... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed June 23, 2014
    Condo was very clean and with chocolates upon arrival. Beautiful island décor and kitchen was well stocked with basics to prepare meals. Plenty of furniture to store your...
    5 of 5 stars Reviewed June 21, 2014
    We loved very minute of our stay in the "Secret Garden" apartment. The property is spotlessly clean, well-equipped and beautifully furnished. We enjoyed breakfasts on the lanai...
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    $250
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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
    • Dryer
    • Mountain Views
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    WE MANAGE OTHER SIMILAR BEAUTIFUL CONDOS IN WAILEA. IF THIS IS NOT AVAILABLE PLEASE CALL OR EMAIL FOR AVAILABILITY! If you are looking for a perfect get away in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi and all the amenities this... View all property information
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    Location Information
    Wailea, Maui 96753
    From
    $216
    / Night
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    1 / 16
    4.5 of 5 stars (2) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Stereo System
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wailea Ekahi 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 well-known... View all property information
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    Wailea, Maui 96753
    From
    $250
    / Night
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    1 / 16
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Grill
    • Satellite TV
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Special Fall 2015 Rates! Please inquire. Grand Champions 163 is a delightful ground floor two bedroom tiled throughout with the exception of the bedrooms. Beautiful, Kitchen and Vanity Cabinets with Granite Counter tops. The Living room has a cozy sectional sofa, flat screen TV, DVD, wireless... View all property information
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    Wailea, Maui 96753
    From
    $750
    / Night
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    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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    $1,595
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    1 / 82
    4 of 5 stars (2) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Grill
    • Dishwasher
    • Air Conditioning
    • Stereo System
    • Internet Access
    • Hot Tub
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
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    Location Information
    Wailea, Maui 96753
    From
    $140
    / Night
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    1 / 27
    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (10) Make Inquiry
    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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    Location Information
    Wailea, Maui 96753
    From
    $995
    / Night
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    1 / 83
    5 of 5 stars (1) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    • Hot Tub
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars 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 "wow" what a...
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    $139
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    1 / 24
    5 of 5 stars (1) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    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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    $540
    / Night
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    1 / 16
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • DVD Player
    • Hot Tub
    • Stereo System
    • Wi-Fi
    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
    From
    $177
    / Night
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    1 / 20
    5 of 5 stars (11) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Stereo System
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Grand Champions #162 is a spacious, one-bedroom, two-bath, ocean view condo. Great 2nd floor, end-unit location for quiet and privacy. Vacation in sunny South Maui in a beautifully furnished, ocean-view condominium at Grand Champions Villas in exclusive Wailea, Maui's premier vacation destination.... View all property information
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    Location Information
    Wailea, Maui 96753
    From
    $209
    / Night
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    1 / 30
    5 of 5 stars (5) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Dryer
    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is a large pool and hot tub that is perfect for... View all property information
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    Wailea, Maui 96753
    From
    $495
    / Night
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    1 / 20
    5 of 5 stars (36) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (36) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Water Views
    • Waterfront
    • Internet Access
    • DVD Player
    • Shared Tennis Court
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade was completed June 2008 resulting in a home away from home with only highest quality finishes.... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed February 25, 2015
    I was told about this condo in Australia and could not believe what I was told...then I arrived there and it was beyond what I could have imagined! The condo is fitted out...
    5 of 5 stars Reviewed February 25, 2015
    Jim’s condo at Makena Surf F304 is outstanding! We’ve stayed at a number of Maui condos over the past 25 years, and spent our annual trip over the last decade in condos in Wailea...
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    From
    $105
    / Night
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    1 / 14
    5 of 5 stars (21) Excellent
    Studio / 1 Bathroom / Sleeps 2
    Overview Reviews (21) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Dryer
    • Wi-Fi
    • DVD Player
    • TV
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    NEXT AVAILABLE SHORT OPENINGS AS LISTED BELOW: SPECIAL, UNIQUE STUDIO IN THE HEART OF WAILEA. YOU MIGHT PAY LESS, BUT YOU CAN'T GET MORE FOR YOUR MONEY! LATE SUMMER RATES $105/NT + $75 CLEANING FEE + HI. TAX 13.42% AUG 1-18, 4 NIGHTS... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed October 1, 2013
    Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
    5 of 5 stars Reviewed September 29, 2012
    We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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    From
    $1,195
    / Night
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    1 / 71
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Dishwasher
    • Stereo System
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
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    Location Information
    Wailea, Maui 96753
    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.