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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 / 17
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 23
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 35
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 22
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Live luxuriously while on vacation! Beautiful Hawaiian art, travertine floors, granite countertops, tall bath vanities, and elegant new furniture make this condo a place of comfort and serenity. The two bedrooms are private, each with an en suite bathroom. The master bedroom offers a California... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed November 9, 2016
    Between the location (walking distance to shopping, great restaurants, grocery stores, coffee and of course THE BEACH) and how nice the condo was made our vacation something our...
    5 of 5 bubbles Reviewed November 1, 2015
    Stayed in this really nice 2 bedroom/2 bath (upstairs) condo that was in a great location in Wailea, Maui. It is located near the Shops of Wailea, beaches, and restaurants (such...
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    1 / 74
    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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    • x
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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 / 25
    5 of 5 bubbles (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Satellite TV
    • Grill
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    About this property
    Here's is your chance to experience this gorgeous condo at the Palms at Wailea. Newly renovated fully air conditioned, Charcoal grey bamboo floors, Whotel Pillow top Cal king mattress including the WHotel feather bed that makes you feel like your floating. There is also 2 flat screen TV's and the... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed May 26, 2016
    We loved our stay at Lawrence's condo. The condo is beautifully remodeled and well-equipped. It is located perfectly between the beaches of Wailea and the cute town of Kihei...
    5 of 5 bubbles Reviewed December 12, 2015
    1st off I have to say... I can't wait to go back to this space!!! My partner and I stayed In Lawrence's beautiful condo! Tasteful and stylish with its decor, with its...
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    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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 / 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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    • Wi-Fi
    • Patio
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
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    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 / 28
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    • x
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    • 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
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    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
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    • Sauna
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    • Pet-friendly
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    • x
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    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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    • Waterfront
    • Air Conditioning
    • 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 3 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
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    • Ocean Views
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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 / 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
    • Air Conditioning
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    • Children's Pool
    • Wi-Fi
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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
    Location Information
    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 / 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
    • Air Conditioning
    • Housekeeping...
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • 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 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
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    • 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 / 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
    • Patio
    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool...
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    • 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 / 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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    • Satellite TV
    • Internet Access
    • Grill
    • 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 / 8
    4.5 of 5 bubbles (19) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • 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 / 23
    5 of 5 bubbles (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • ?
    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 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Terrace
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    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful two bedroom (with queen beds), two bath condo is in a 150-unit complex, unit #704. Our second (top) floor location allows for privacy and the ability to leave the doors wide open to welcome the tropical breezes. A short walk to fabulous Wailea beaches and an even shorter walk to the... 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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    • x
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    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 / 82
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • ?
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    • ?
    About this property
    <b>Sandy Surf K508 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> The Wailea Beach Villas is ranked... 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
    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
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    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 / 19
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Spring Saver Rates 2017! Book Early ! 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
    1 / 24
    4 of 5 bubbles (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious living room opens to the Lanai, where there is ample space for stretching out and relaxing in the sun, barbecuing on your own private grill, or admiring the tropical grounds of The Palms at Wailea.... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed February 15, 2015
    This is a terrific location for a visit to South Maui. We used the whale watch rafts from the Kehei ramp. Close to Safeway, beaches with full service and beach parking. Loved...
    4 of 5 bubbles Reviewed August 2, 2014
    We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
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    1 / 16
    4.5 of 5 bubbles (21) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • x
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    • x
    About this property
    About this condo: Wailea Elua Village #1402 is a 2nd story, one bedroom, one bath oceanfront condo complete with a fully remodeled kitchen, new carpet and a sofa sleeper. Enjoy the complimentary wireless internet service on your lanai as you enjoy the beautiful view of the sun-kissed Ulua Beach.... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed June 19, 2014
    My wife & I stayed at Elua #1402 from 5/31-6/7/14. This was our second stay in 1402 and we will undoubtedly be back. The unit is very well located within the complex as it has...
    5 of 5 bubbles Reviewed June 10, 2012
    My wife and I stayed at Wailea Elua 1402 from 5/27/12 to 6/4/12. We have stayed in Wailea during nearly 10 vacation trips over the past 20+ years, at the former Stouffers Resort...
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    1 / 18
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Air Conditioning
    • Balcony
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    • Shared Outdoor Pool...
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    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 / 60
    5 of 5 bubbles (1) Excellent
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
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    About this property
    Coral Gardens Estate at Makena Bay is a legal permitted short-term vacation rental home. The permit license number is: STKM 2013/0011. The transient tax ID number is: TA-191-865-0368-01. <b>Coral Gardens Estate at Makena Bay is located on Maui island, voted #1 best island in the WORLD by... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed July 23, 2015
    This was our fourth trip to Maui and it was the best. Thanks to Coral Gardens in Makena. The luxury home is perched on Makena Bay ('turtle town') and did not disappoint. We were a...
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    1 / 31
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool...
    • Air Conditioning
    • Washer
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a recently renovated luxury first floor condo in Wailea's premier Grand Champions Villas. Our home is unit #103 on the east side of the complex. Spend your vacation enjoying this 1 bedroom, 2 bath unit that provides ample space to spread out,... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed April 23, 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 bubbles Reviewed September 10, 2013
    I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
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    1 / 16
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 22
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
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    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool...
    • DVD Player
    • Washer
    • Grill
    Suitability
    • 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
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    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 / 23
    4.5 of 5 bubbles (12) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
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    • Grill
    • Air Conditioning
    • 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
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    Wailea, Maui 96753
    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...
    5 of 5 bubbles Reviewed March 2, 2015
    This is a spacious condo with all the amenities you'd want for your vacation -- including a washer and dryer inside the condo and a full patio with BBQ. The setting is beautiful...
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    1 / 86
    5 of 5 bubbles (2) Excellent
    Studio, 4 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Patio
    • Satellite TV
    • Washer
    • Shared Outdoor Pool...
    • Wi-Fi
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
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    About this property
    <b>Castaway Cove C201 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> The Wailea Beach Villas is... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed January 17, 2016
    Really cannot think of any negatives. The location of the villa was terrrfic; it was well appointed and staff was superb.
    5 of 5 bubbles 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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    1 / 16
    5 of 5 bubbles (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    About this condo: Wailea Elua Village #2306 is a two bedroom, two bath second floor unit with beautiful ocean and mountain views that has been completely remodeled and upgraded with marble floors and granite counter tops, all new appliances, all new furniture, all new fixtures, top of the line Sony... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed January 30, 2015
    The condo was extremely comfortable and very well equipped. The views of the ocean and the grounds were fantastic and the sounds of the waves crashing and the birds singing were...
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    1 / 19
    4.5 of 5 bubbles (17) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax in the luxury and convenience of being in a world class resort, but enjoy the privacy and beauty of our fabulous 2 bd/2ba ground floor "home away from home" that fronts the 7th Fairway of the famed Wailea Blue Course. Our spacious 1100 sq ft. unit has a tropical decor with world-class art... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed May 3, 2015
    Stayed here with my husband, toddler and my parents - and it was perfect. The location is right by beaches, shops and restaurants. Also, there are boogie boards, snorkeling...
    5 of 5 bubbles Reviewed November 7, 2011
    The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea, the...
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    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 3 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 / 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
    Suitability
    • 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 / 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
    • ?
    • 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 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • DVD Player
    • Grill
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 TV, iPod docking station, new couch and living... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 bubbles (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Notes from the Owners: Wailea Elua Village #1204 is a beautiful two bedroom, two bath oceanfront condo that has been fully remodeled with top of the line appliances and the latest in furnishings. The large travertine flooring in the kitchen, dining, living and baths provide a cool walking surface... View all property information
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    Wailea, Maui 96753
    1 / 74
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Parking
    • Hot Tub
    • Air Conditioning
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
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    About this property
    <b>Orient Pacific Suite J505 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> The Wailea Beach Villas... View all property information
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    Wailea, Maui 96753
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Spring Saver Rates 2017 - Book Early! Use Promo Code: SPRINGSAVER!! Wailea Ekolu 1606 is a top floor two bedroom two bath condo with a wonderful ocean view. Beautiful wood flooring throughout, vaulted ceilings, spectacular kitchen and classy island decor. The living area is Air Conditioned, has a... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A Note From the Owner: You will love the extra space in this remodeled supersized two-bedroom, two-bath Elua condo. With nearly 300 square feet more than the typical Elua two-bedroom unit, you can spread out, relax and truly enjoy your stay in paradise. Our large lanai, living room and master... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed October 26, 2014
    We stayed at Wailea Elua 2107 for a week in October. The view from the front lanai is outstanding and the rear lanai is very private. We used the barbecue once and it worked fine...
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    1 / 16
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Private Outdoor...
    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
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    Wailea, Maui HI
    1 / 24
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Newly remodeled, Two bedroom / Two bathroom, second floor condominium right on the Beach! It is perfect for two couples or a family of four. You are literally steps from the beach! This condominium is at the front of the building closest to the ocean making for spectacular views! Upgraded... View all property information
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    Wailea, Maui 96753
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Wailea Ekolu Village is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low density village consists of eighteen two-story buildings spread out over 18 acres of tropical landscaping and is conveniently located across... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Grill
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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 / 20
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Waterfront
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Spring 2017 Discounted Rates ! Promo code: SPRINGSAVER! This condominium home has been beautifully upgraded throughout and boasts a wonderful kitchen, dining room and living room. Summer 2014 new carpet was added throughout and new living room furniture greets you as you walk in the front door. The... View all property information
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    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.