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Condos and Vacation Rentals in Wailea, HI

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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 25
    5 of 5 bubbles (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 17
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    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
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 4 weeks ago
    This condo was great for location and proximity to good walking in Wailea. The pool and beach area was amazing. The Barbecue facilities were at the opposite side of the complex...
    5 of 5 bubbles Reviewed October 25, 2016
    This place is truly a paradise of sorts. Close to the beach and the condo itself is very clean, well kept and has everything you need to enjoy your stay. The Condo is stocked...
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    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    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 bubbles 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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    1 / 23
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • x
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    About this property
    Aloha Maui vacation planners, Welcome to beautiful Wailea, a Master Planned Community which ensures good community planning and utilizes design guidelines to help preserve Maui's sophisticated island environment. Grand Champions Villas is located in the heart of Wailea and nestled between The... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed October 6, 2016
    This was a wonderful vacation for myself, husband and daughter. We were delighted with our stay and all the tips left by Paul and Jessica. So close to beaches and excellent food...
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    1 / 28
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Bring the most special person in your life to our beautiful condo. Our condo has one of the best ocean views in ekolu. Experience the pleasure of tropical living in a quiet and relaxing environment. Enjoy a tranquil retreat overlooking the ocean with breathtaking views of Molokini. Completely... View all property information
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    Wailea, Maui 96753
    1 / 35
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
    • Wi-Fi
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    • Mountain Views
    • Ocean Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 bubbles Reviewed December 11, 2016
    The owner, Cara, was great to deal with by email, everything that was represented of the property was true. It was a lovely home away from home, very comfortable and great...
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    1 / 14
    5 of 5 bubbles (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Ocean Views
    • Hot Tub
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    SUMMER SPECIAL: Stay 2 weeks in June/July for only $175/night. Simply request the special rate when you inquire. If you love to swim in the ocean, if you have kids who like to play in the sand and go wading, if you want to stroll on a beach holding hands as the sun sets, then our well-equipped,... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed November 10, 2016
    There were 7 adults why stayed in this place. It was dated, but clean and lovely! Would stay again!!
    4 of 5 bubbles Reviewed October 30, 2016
    A lovely comfortable condo with plenty of space for two couples, equal standard rooms and bathrooms for each. A couple of minutes walk to an uncrowded extremely clean beach, and...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Ocean Views
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    • Hot Tub
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    QUIET PRIVACY IN PARADISE This is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations in the property. Often the only sound you will hear is the waves crashing on the nearby beaches. The Palms at Wailea is one of the upscale... View all property information
    Location Information
    Wailea, Maui 96753
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    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 square foot villa with large... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed November 29, 2016
    Well stocked kitchen, very nice bathrooms, ample sized bedrooms except the smaller one downstairs. Good location.
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    1 / 24
    5 of 5 bubbles (23) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Washer
    • Mountain Views
    • DVD Player
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    • Patio
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 and 1/2 baths, 550 sq. ft. completely furnished cottage with full kitchen. This cottage has it all. Spectacular furnishings and ocean views! Completely remodeled 1 bedroom cottage in Maui Meadows... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 4 weeks ago
    Such a beautiful cottage!! Pictures do not do it justice. Dennis was amazing and very helpful upon arrival, even brought us fresh fruit from his trees. Very clean well cared for...
    5 of 5 bubbles Reviewed 4 weeks ago
    So... I can't believe our Maui dream vacation has already come to an end. It went by so fast, but I am left with some amazingly wonderful memories of our stay at Dennis' Maui...
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    1 / 14
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool...
    • Ocean Views
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Our beautiful ocean view unit is situated in upper Wailea Ekahi Village. It is a 952 square foot unit on the second floor with one bedroom and two full bathrooms. It comfortably sleeps 4 guests. Two in the bedroom and two on the memory foam sofa sleeper. It is conveniently located near one of the... View all property information
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    Wailea, Maui 96753
    1 / 8
    4.5 of 5 bubbles (19) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Waterfront
    • Washer
    • Patio
    • Internet Access
    • Grill
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Located on world famous Keawakapu Beach in Wailea, Ekahi Village is one of the most sought after locations. Our totally renovated condo offers complete privacy, but is only steps to the beach. Unwind after a day at the beach or pool by watching our 46" Sony Bravia flat screen with surround sound... View all property information
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed September 12, 2016
    A wonderful, spacious one bedroom condo. No view of water, just lush greenery since its a ground floor unit. Very close to pool and beach access. Wailea shopping just a short...
    4 of 5 bubbles Reviewed February 27, 2013
    My husband and I stayed in this unit for 3 weeks another couple joined us for 2 weeks. The owner was easy to work with and provided all the needed information to make our stay...
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    1 / 14
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Balcony
    • Satellite TV
    • Hot Tub
    • Wi-Fi
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    • Shared Outdoor Pool...
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Spring Saver Rates 2017 Super Specials - Book Early !! All New Upgraded Kitchen and Baths. Grand Champions 54 offers a large 54" flat screen TV, DVD player, CD player, Ipod dock, high speed and wireless internet. The living room has air conditioning, ceiling fan and vaulted ceiling with a separate... View all property information
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed November 23, 2011
    We had stayed at Grand Champions last year so we were familiar with the complex and the location.....both reasons why we chose to come back here. This upstairs unit is pretty much...
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    1 / 23
    4.5 of 5 bubbles (12) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Waterfront
    • Satellite TV
    • DVD Player
    • Washer
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed yesterday
    This the second time we have rented this unit in the last 2 years. We have been very satisfied with our experience. Well maintained and good prices. Easy walk or drive to beach...
    5 of 5 bubbles 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...
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    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Wi-Fi
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our home is set up for up to 8 guests to sleep comfortably. Two of the bedrooms have private full bathrooms. It's within a 4-6 minute walk to Charley Young and Kamaole One beach park. It is centrally located close to many shops and restaurants so walking is a real treat! We have an elevator and... View all property information
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    Wailea, Maui 96753
    1 / 22
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Mountain Views
    • Wi-Fi
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    • DVD Player
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed September 6, 2016
    Travelled with my wife and two teenage sons. Condo was very roomy and was located on the fairway #2 of the Blue course. Was a quiet unit with very nice views towards the ocean...
    5 of 5 bubbles 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...
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    1 / 13
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Satellite TV
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Spring Saver Rates 2017 ! Grand Champions 122 offers a large flat screen TV, DVD Player and CD Player. The living room has air conditioning, ceiling fan and vaulted ceiling. There is a separate dining area. The lanai also has a table and chairs to enjoy the outside view. The kitchen is remodeled... View all property information
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    Wailea, Maui 96753
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • x
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    • x
    About this property
    A note from the owner. Welcome to our Maui ohana. Our unit is special because of the extra space and privacy, including the cool, shady side lanai we call our grotto - the perfect place to curl up with a good book, and a lovely respite from the afternoon heat! From our ocean lanai, we like to watch... View all property information
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    Wailea, Maui 96753
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    1 / 14
    4 of 5 bubbles (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
    • DVD Player
    • Internet Access
    • Terrace
    • Shared Outdoor Pool...
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Special Spring Saver Rates 2017 - Book Early! Promo Code SPRINGSAVER. A spacious two bedroom two bath condominium in beautiful Wailea. A partial ocean view, BBQ grill and comfortable lanai furniture to enjoy while relaxing in tropical breezes. The kitchen is well equipped, has granite counters and... View all property information
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    Wailea, Maui 96753
    1 / 23
    4 of 5 bubbles (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Waterfront
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    • x
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    • ?
    About this property
    Great Spring 2017 Promo - Coupon Code: SPRINGSAVER!! Wailea Ekahi #38B is a charming condominium furnished with a King bed in the master bedroom, Queen pull out sofa sleeper in the living room, is fully air conditioned and has Free parking and wireless internet access. There are ceiling fans... View all property information
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    Wailea, Maui 96753
    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautifully furnished and well appointed, with gorgeous views and 3 large Lanais. This is a very comfortable "home away from home" with many special amenities, full kitchen and BBQ. Newly remodeled and next to the Quiet Upper Pool, it is private, quiet and very spacious 1550 sq ft. Surrounded by... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed July 24, 2016
    This is the perfect place to stay while exploring Maui. The Condo is in a superb landscaped setting and is fully equiped with everything that you are likely to need. If you read...
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    1 / 12
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 bubbles Reviewed August 24, 2016
    Loved the location and amenities. Very nice kitchen and master bathroom. We would stay there again. Hope the TV gets fixed. Disappointed we were unable to watch the Olympics...
    5 of 5 bubbles Reviewed July 13, 2016
    Beautiful place, great view, great location. Spacious condo with a great floor plan and within walking distance to the Wailea Mall. The beach is a short drive away. I would love...
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    1 / 20
    5 of 5 bubbles (37) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 has been completed resulting in a home away from home with only highest quality finishes.... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed February 27, 2016
    Welcome basket with tasty local treats greeted us! Makena Surf is a super location on Maui - front row seats to see whales in February (bring binoculars), steps from the beach...
    5 of 5 bubbles 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...
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    1 / 20
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Spring Saver Rates 2017 - Book Early ! Beautifully decorated and fully renovated two bedroom condominium with garden, some ocean and mountain views. Beautiful new tile floors throughout, designer painted, granite counters, new furniture and beautiful art all for you to enjoy. The living room has... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Special Spring 2017 Promo - Book Early Use Promo Code SPRINGSAVER! 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... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed September 15, 2015
    We stayed at Wailea Ekahi in unit 35B in October and really really enjoyed it. . A favourite happy hour spot was the upper balcony. We loved the ground floor patio and ate our...
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    1 / 24
    5 of 5 bubbles (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Housekeeping...
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Polo Beach Club sits on quiet Polo Beach. It is a unique building located within feet of the beach. Our home is a completely remodeled 2 bedroom 2 bath unit. We always provide daily maid service and upon arrival you will receive a complimentary fruit basket. When you first enter our home look... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 4 weeks ago
    Entering this condo takes your breath away. The palm trees, waves, beach, and whales! Yes, whales were waving welcome to us. Perfectly appointed from art to kitchen accoutrements...
    5 of 5 bubbles Reviewed December 10, 2014
    My wife and I have stayed in many locations in Hawaii in general and Maui in particular, but, overall, none can compare to the Polo Beach Club and in particular THIS unit. While...
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    1 / 23
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Parking
    • Balcony
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    • Washer
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Tropical paradise is made even more magical with this luxury vacation rental. With a third story location that has views of the Pacific and ample entertaining space both indoors and out, we're certain your Maui vacation will be unforgettable. The open floor plan features tile throughout to keep the... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 bubbles (30) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Grill
    • Patio
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Ekahi 1BD/2BA 20B is a beautiful, 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 with all your beach gear... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed July 24, 2016
    Great. Would return. Close to beach. Comfortable beds. Beautiful community. Nice pools. Shopped at costico close by. Great value. Great patio.
    5 of 5 bubbles Reviewed March 15, 2016
    This rental is fantastic, my wife and my 2 year old went in February. Not only was the rental a great space, with nice appliances (and the sharpest chef knife I've ever had in a...
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    1 / 16
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second floor. Sitting on the lanai at sunset, we feel the... View all property information
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    Wailea, Maui 96753
    1 / 29
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Satellite TV
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    • Washer
    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Ask us about our other Ekahi Village condos for rent Aloha ! Condo # 50-C - Luxury at an affordable price - perfect for a getaway or honeymoon. (4maximum) Low Season rate (Apr 16 - Dec 15) $175.00 per night High Season rate (Dec 16 - Apr 15) $275.00 per night This is a romantic 1bed/1bath,... View all property information
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    Wailea, Maui 96753 9533
    3 of 5 bubbles Reviewed February 2, 2012
    This one-bedroom condo (with hide-a-bed couch in living room) was obviously recently updated - the kitchen, bathroom and bedroom all had nice, tasteful, simple furniture...
    5 of 5 bubbles Reviewed May 4, 2011
    I don't know about you, but if I wanted to stay in a resort with a million it other people and had a 3 mile treck to the beach or pool....I could stay anywhere! Valley Isle #302...
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    1 / 34
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
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    • Children's Pool
    • Air Conditioning
    • Satellite TV
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    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wailea Ekahi 20F is a 2 bedroom unit featuring panoramic ocean views, a great, quiet location with a short, 2 minute walk to Keawakapu Beach. As new owners, we welcome you to enjoy our condo and all that it has to offer! Wailea Ekahi Village is a premier ocean front condominium community located... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed August 17, 2016
    Me and my family had a wonderful visit at Ekahi 20F! The view was beautiful and th beach was so close! The condo was amazing and we had so much fun hanging out and using all of...
    5 of 5 bubbles Reviewed August 17, 2016
    This condo worked out great for our family of four. I do a lot of research when booking a rental, and I know what I want. So, the best outcome is when the place turns out to be...
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    1 / 28
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Mountain Views
    • Children's Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This One-of-a-Kind Maui Getaway is just the vacation destination you have been dreaming of! Owner and architect Kyron Brimmer, designed this unique and modern 4 bedroom, 4 bath Hawaiian style home with the guest in mind. From pencil sketch to sustainable masterpiece, it captures Maui’s tropical... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 3 weeks ago
    The house is beautiful, located in the best are of Maui, with killer views!!! Every thing in the house is spotless. Its better than a 5 star hotel!!!
    5 of 5 bubbles Reviewed November 30, 2016
    We rented this wonderful home for our 40th wedding anniversary. Our daughter, son-in-law, son and daughter-in -law were with us for our week long celebration. This is the most...
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    1 / 16
    4.5 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the property is exceptional... View all property information
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    Wailea, Maui 96753
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful 2BR/2BA Condo in Wailea located in the amazing Grand Champions Villas complex. Only a 5 minute walk to the beach, Grand Champions provides a luxurious, relaxed vibe in the beautiful town of Wailea. Close to numerous restaurants, shops and beaches. Relax in the two pools on property or... View all property information
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    Wailea, Maui 96753
    1 / 18
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    About this property
    Spring 2017 Deals Available! Book Early! Promo Code: SPRINGSAVER! Wailea Ekahi #41B is a lovely ground floor condominium furnished with a King bed in the master bedroom as well as air conditioning in both the living room and bedroom. There are ceiling fans throughout, Flat screen TV in living room... View all property information
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    Wailea, Maui 96753
    1 / 19
    5 of 5 bubbles (7) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Shared Outdoor Pool...
    • Grill
    • Balcony
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Special Spring Promo 2017 Code: SPRINGSAVER !! 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,... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed August 8, 2015
    I cannot express enough how wonderful our two week vacation was in Maui. Our family of six (with four teens) built memories that will last a lifetime. Ho'olei was the PERFECT...
    5 of 5 bubbles 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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    1 / 26
    4.5 of 5 bubbles (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveler has booked this property
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    • Grill
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    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed December 7, 2016
    Steve and Tamara's studio was just what I was looking for. A gated community central to everything in Wailea area. Nicely appointed studio, includes washer/dryer on lanai. Large...
    4 of 5 bubbles 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...
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    1 / 27
    5 of 5 bubbles (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Satellite TV
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    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 16
    5 of 5 bubbles (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • 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 bubbles Reviewed May 11, 2016
    We stayed in the #801 condo in April 2016. In general, the Wailea Elua Village is a unique site. It is extremely well maintained, the surrounding park is beautiful, we had the...
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    1 / 16
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • DVD Player
    • Hot Tub
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    • Shared Outdoor Pool...
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Spring Saver Rates 2017 Book Early Code: SPRINGSAVER !! Grand Champions 118 is an inviting and cozy two bedroom two bath condominium. The kitchen and both baths have been remodeled spring 2013!! The condo has air conditioning, ceiling fans, a 54' flat screen TV, DVD player, iPod docks and free high... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Waterfront
    • Shared Outdoor Pool...
    • Satellite TV
    • Grill
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Spring 2017 Specials - Book Early Promo Code: SPRINGSAVER ! Wailea Ekahi #3C is a charming one bedroom, one bath, first floor garden view condo. It is a great choice for singles or couples wanting a reasonably priced condo close to the beach. The private garden setting is great for relaxing and... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed November 4, 2011
    We love staying at Ekahi Village condos. We have stayed here multiple times, this last time in 3C. What we love most is that there are no surprises, everything is exactly as...
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    1 / 23
    5 of 5 bubbles (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Grill
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    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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    Wailea, Maui 96753
    5 of 5 bubbles 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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    1 / 16
    5 of 5 bubbles (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • DVD Player
    • Hot Tub
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the property is exceptional... View all property information
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed May 26, 2012
    We stayed in this corner condo unit with views of Chang's beach and the southern coast of Maui. The expansive view from the balcony (glass all around) was the best part....we've...
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    1 / 58
    5 of 5 bubbles (7) Excellent
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • ?
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    About this property
    <b>Sunny Surf E301 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016.</b> Recently introduced to our... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed October 25, 2015
    Once entering the property which is quite secure, and meeting the friendly and helpful owner, you are taken through a wonderful tropical and well maintained garden around a...
    5 of 5 bubbles Reviewed May 23, 2015
    When I was planning our family vacation for my wife and 2 adult sons, I spent countless hours researching, talking to friends, etc. As I am a supporter of Tripadvisor, I also...
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    1 / 19
    5 of 5 bubbles (46) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 4 weeks ago
    This condo was perfect! We had ocean views from two lanais and it was less than 5 min. stroll to pool and amazing beach. The condo was extremely clean and well-appointed with...
    5 of 5 bubbles Reviewed November 27, 2016
    My wife and I along with another couple just returned to the mainland after spending three fabulous weeks at Lynn & Sharon's condo. Their unit, 28-D, is located in the Wailea...
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Grill
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 18
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    • Grill
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Special Rates Available for the Spring of 2017 - Promo Code: SPRINGSAVER! This ground floor, Wailea Ekahi condominium has a garden and partial ocean view. There is a King bed in the master bedroom and Queen pull out sofa sleeper in the living room. Air conditioning in both the bedroom and living... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles 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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    1 / 13
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Grand Champions 86 is perfect for two people. The living area is air conditioned and has ceiling fans, vaulted ceiling, comfortable sectional sofa, separate dining area, flat screen TV, DVD player, high speed and wireless internet. The oversize lanai offers beautiful ocean view while overlooking... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed August 21, 2014
    A very well equipped condo with starter pack of coffee (essential) and other pantry basics. The condo also included new beach towels, decent beach chairs, umbrella, beach mats...
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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.