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Villas in Wailea, HI

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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Mountain Views
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    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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 2 weeks ago
    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 / 15
    5 of 5 stars (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 stars Reviewed 29 March 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 / 22
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This ground floor corner villa at Grand Champions Resort features three bedrooms, two baths, a fully equipped gourmet kitchen, and two lanais. Surrounded by the manicured fairways of Wailea's famed Blue Golf Course and the spectacular grounds of the Wailea Tennis Club, this quiet, well-managed... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 21 April 2015
    The condo was spacious, clean and homely. They had everything we needed and the complex was well maintained. very close to Wailea town centre and 15 min walk to resort area. BBQ...
    4 of 5 stars Reviewed 22 December 2013
    We were a group of 6 adults and one toddler and we felt totally at home here and would definitely recommend this condo our friends. Set in an amazing area with world class...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • x
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    • 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 / 24
    5 of 5 stars (18) 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, 500 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
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 22 May 2016
    My other half and I decided to try this beautiful cottage for two weeks, once we found what we thought would fit our needs & wants, we booked it. Wow did we ever come across a...
    5 of 5 stars Reviewed 2 March 2016
    These photos don't do the cottage justice ! It's really special and highly recommended cottage for 2 to re-charge your batteries in. We spent 8 nights here unwinding, relaxing up...
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    1 / 74
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • 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
    5 of 5 stars Reviewed 16 September 2014
    I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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    1 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Satellite TV
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    • Shared Outdoor Pool...
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    • Balcony
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    • Pet-friendly
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    • x
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    About this property
    Please ask for our Spring 2016 Special Rates!! This beautiful condo has been upgraded throughout. It has a king bed, air conditioning in the living room, bedroom and ceiling fans throughout. The extended lanai runs the full length of the condo. Conveniently located, this condo is just a short walk... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 16 July 2014
    Very well appointed unit and beautifully maintained grounds. Went over for my niece's wedding. We had a pre-wedding function with 15 people and everything had we needed...
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    1 / 18
    5 of 5 stars (34) Excellent
    1 Bedroom, 3 Bathrooms, Sleeps 3 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    EXCELLENT LOCATION, BEAUTIFUL & PRIVATE OCEAN VIEW! Watch the surf, check out the beach and listen to the rhythm of the waves breaking onto black lava rock. Completely remodeled, refurnished & professionally decorated. Enjoy wonderful ocean, tropical gardens and Haleakala views. A true "Paradise... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 20 February 2016
    Every year we ask ourselves why staying in Ekahi 7G has become our favorite vacation spot? Could it be the beautiful decor we see every time we enter? Or perhaps it's because the...
    5 of 5 stars Reviewed 27 July 2014
    Just returned from Maui and Wailea Ekahi 7G delivers everything promised. The unit is beautifully decorated and has every imaginable amenity. The kitchen is extremely well...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • Ocean Views
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    • Housekeeping...
    • Satellite TV
    • DVD Player
    • Wi-Fi
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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
    1 / 17
    5 of 5 stars (4) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Satellite TV
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Total renovation with high end finishes. All amenities: AC, HDTVs, free phone calls to US & Canada, free WIFI, Stainless Steel appliances, granite counters. Located in the upper part of Ekahi Village, an Ocean-Front community located on Keawakapu Beach, Wailea, South Maui. Non-Smoking ground floor... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 15 November 2014
    This condo was clean, well-equipped, and a five minute walk from the beach. The grounds were magnificent and even had an orchid garden. There was great snorkeling right off the...
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    1 / 8
    5 of 5 stars (17) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Waterfront
    • Washer
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    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 stars Reviewed 28 February 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 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Mountain Views
    • Internet Access
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    WE MANAGE OTHER SIMILAR BEAUTIFUL CONDOS IN WAILEA. IF THIS IS NOT AVAILABLE PLEASE CALL OR EMAIL FOR AVAILABILITY! <BR><BR>If you are looking for a perfect get away in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi and all the amenities... View all property information
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    Wailea, Maui 96753
    1 / 23
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
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    • Hot Tub
    • Patio
    • Shared Outdoor Pool...
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
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    About this property
    Welcome to our home! Enjoy the fantastic ocean views and luxury of our home in Wailea Elua Village - a gated, 24 acre, oceanfront community. Our home is perfectly situated in the center of the Wailea Elua Village property (Unit #701). We are 150 yards from Ulua Beach -- just a 90 second walk to... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 12 October 2015
    My sister and I stayed at this condo for five nights in September. The condo is in the perfect location within Elua Village. The beach and pool pavilion are only a few minutes...
    5 of 5 stars Reviewed 7 August 2014
    We stayed for five days in July with 2 children and 2 adults. The unit was exactly as advertised and had everything and more that we needed during our stay. The view from lanai...
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Hot Tub
    • Sauna
    • Patio
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    • DVD Player
    • Waterfront
    • Ocean Views
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located across the street from the world renowned Wailea Beach, Ho'olei 81-1 is unequaled in splendor, elegance and convenience. Let this exceptional three bedroom, three and a half bath, two-level residence be your home away from home for your dream Hawaiian vacation. Every aspect of this... View all property information
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    Wailea, Maui 96753
    1 / 67
    4 of 5 stars (13) Very good
    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    About this property
    <b>Wailea Sunset Estate is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> Wailea Sunset Estate, one of our most popular vacation homes, was just lovingly refreshed with some upgraded amenities and decor. We installed brand new flat... View all property information
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    Wailea, Maui 96753
    1 / 42
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
    • DVD Player
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    • Mountain Views
    • Wi-Fi
    • Children's Pool
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Look no further!!!! Luxurious and exclusive 2 bedroom + den, penthouse unit, now offered at an AMAZING RATE!!!!!! Over 1900 sq. Ft + lanai! Panoramic ocean views, spectacular Hawaiian sunsets!!! Wailea Beach Villas VOTED #1 RESORT IN HAWAII BY CONDE NAST TRAVELER NOVEMBER 2014!!!!... View all property information
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    Wailea, Maui 96753
    1 / 12
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Balcony
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Reviews praise this "EXCEPTIONAL OCEANFRONT CONDO" that's just a few steps to its soft sand beach! "Sunsational" newly remodeled condo offers island living at its best in Maui's finest area. The penthouse is only available to ADULT NON SMOKERS... Enjoy Wailea-Makena and the resort's best... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 13 August 2013
    My husband and 2 sons stayed in this beautiful condo last week. It is quite a place! Every attention to detail is incredible from the beginning correspondence from the owner until...
    5 of 5 stars Reviewed 8 July 2013
    Since our last review, we have stayed there twice. The owner has not only maintained the condo in pristine condition but has updated the master bedroom and bath. The owner is...
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    1 / 20
    4.5 of 5 stars (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Special Rates Summer & Fall 2016 ! This condominium home has been beautifully upgraded throughout and boasts a newly remodeled kitchen, dining room and living room. Summer 2014 new carpet was added throughout and new living room furniture greets you. The comfortable bedroom has a king bed and... View all property information
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    Wailea, Maui 96753
    1 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • 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 stars Reviewed 13 July 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
    5 of 5 stars Reviewed 3 March 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 / 14
    5 of 5 stars (21) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
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    • Patio
    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    NEXT AVAILABLE SHORT OPENINGS AS LISTED BELOW: SPECIAL, UNIQUE STUDIO IN THE HEART OF WAILEA. YOU MIGHT PAY LESS, BUT YOU CAN'T GET MORE FOR YOUR MONEY! AUG 5 - 10 $88/NT + $80 CLNG + TAX 13.42% AUG 14-16 " " "... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 1 October 2013
    Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
    5 of 5 stars Reviewed 30 September 2012
    We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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    1 / 26
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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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!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 31 August 2015
    This spacious studio was perfect for my needs. it was super comfortable and very very clean and there were little touches of extras like the chips and Karens bread in the...
    5 of 5 stars Reviewed 4 May 2015
    I loved this studio. It was very nice space with a deck. It has a stackable washer/dryer. The bed was super comfortable and owners were responsive to my needs. At the time I was...
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    1 / 35
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
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    • DVD Player
    • Mountain Views
    • Ocean Views
    • Washer
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    • 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
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Satellite TV
    • Hot Tub
    • DVD Player
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    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This large 2 bedroom 2 bathroom villa has stunning views of the Old Blue Golf Course. Our spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. <BR><BR>Our condo has has a great layout for two couples. Each couple has there own... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 26 October 2015
    This is the second time I stay in this complex of apartments and I love it so much. It has everything; washing machine, dryer, dish washer, coffee maker and even boogie boards for...
    5 of 5 stars Reviewed 16 December 2013
    My wife and I stayed in unit 29 at the Grande Champions Golf Villas for two weeks in December, 2013. The property manager Kathleen was fantastic to deal with and responded...
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    1 / 20
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Air Conditioning
    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Special Spring 2016 Rates - Please inquire. This beautifully updated condominium offers ocean views and greenbelt views. It has a king bed, queen sofa sleeper, air conditioning in the living room and bedroom, ceiling fans throughout and an extended lanai that runs the length of the unit. Beautiful... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 13 September 2015
    My wife and I were married in Maui and have had family members who lived on Maui for many years, so we have stayed in condos,and hotels all over the island and I can honestly say...
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    1 / 37
    5 of 5 stars (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Housekeeping...
    • Mountain Views
    • Children's Pool
    • Sauna
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    GRAND WAILEA RENTAL PROGRAM BENEFITS FOR OUR GUESTS: * Complimentary on-demand transportation to and from The Grand Wailea Resort * Enjoy the use of all the pools, water slides, spa and restaurants at The Grand Wailea Resort * Exclusive charging privileges at The Grand Wailea Resort *... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 27 November 2015
    Aloha! We have stayed at Hoku Ho'Olei for the past 4 years and I have already booked my trip for July, 2016! Love this villa and the owners. Very beautiful, comfortable and all...
    5 of 5 stars Reviewed 12 August 2014
    I must say that this was one of the best vacation rentals I've stayed at. The house, staff and property was simply amazing. Everyone there was extremely courteous, friendly and...
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
    • Balcony
    • DVD Player
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    • Pet-friendly
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    • x
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    About this property
    • Spacious living room and bedroom with ocean view and vaulted ceiling • Brand new BeautyRest air-cool pillow-top king size mattress • Very quiet split ACs in living room and bedroom with separate controllers. • TV/DVD/Cable in living room and bedroom, queen-size sofa sleeper • Free Wi-Fi access,... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • 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 stars Reviewed 27 October 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 / 24
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Unit 181 is located in the heart of the beautiful and serene Grand Champions Villas. On the edge of the Wailea Blue Golf course, this condo is great for the golfing couple looking for a tropical getaway. Large green belts, manicured grounds and wide golf course fairways abound. Nearby shopping,... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 26 May 2015
    This is a great condo. We were little unsure because it had no reviews but we are very happy that we booked it. It is renovated, with 2 bathrooms (each has a toilette as well...
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    1 / 21
    5 of 5 stars (14) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
    other traveller has booked this property
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    • Ocean Views
    • Wi-Fi
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Maui Rendezvous, Wailea Ekahi 33A, is a luxury (beautiful, romantic, and family friendly) 1,100 square-foot 1 bedroom 2 bath condo that sleeps 5. It is in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 14 September 2014
    We loved the condo and the owners are great. We also loved it as a base camp for exploring the island. Very convenient to other resorts and highways. They provide everything you...
    5 of 5 stars Reviewed 10 September 2013
    Our family of 3 stayed at Maui Rendezvous for 4 nights in August. We had a great time! The condo was clean and spacious. It was well equipped and everything was in good...
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    1 / 24
    4 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Hot Tub
    • DVD Player
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    • Shared Outdoor Pool...
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Welcome to your home away from home! This beautifully remodeled 2-bedroom condo is a guest favorite. You'll enjoy the open layout, as well as the many upgrades that this condo has to offer. Entering the condo, you'll find yourself in the spacious and bright living room, which has been newly... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 26 October 2014
    We cannot seem to branch out from the Palms at Wailea having stayed here a dozen or more times in the last decade. We have used many units for many purposes bring anywhere from 2...
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    1 / 20
    5 of 5 stars (37) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
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    • Washer
    • Satellite TV
    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 stars Reviewed 28 February 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 stars Reviewed 26 February 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 / 16
    4 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    A Note from The Owners: Our dream-come-true was to have a unit directly overlooking the beach at Makena. We can literally talk to each other from the lanai to the beach! We did a remodel which, among other features, allows us to push all the glass doors back into the wall and open the entire living... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 25 August 2014
    After hours spent on the net to search for THE place to stay, I found Alii's resort website, offering several condos in this residence. Prices are upscale but it is worth the...
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Satellite TV
    • Balcony
    • Grill
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Surround yourself with the lush, natural beauty of Hawaii, starting with your choice in accommodations. Maui Breeze Retreat is a luxurious, privately-owned townhome nestled in Ho’olei, located near the Grand Wailea Hotel & Spa and Four Seasons Resorts on the beautiful island of Maui. Your... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Special Spring 2016 Pricing - Please Ask. Wailea Ekahi Village 35B is where you want to be. It is the paradise you have been looking for. Walking through the landscaped grounds, you are surrounded by beautiful orchids, ginger, bougainvillea and hibiscus flowers. Both bedrooms are furnished with... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 16 September 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 / 58
    5 of 5 stars (7) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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!</b> Recently introduced to our exquisite villa collection is "Sunny Surf" E301 at Makena Surf, a sophisticated executive-style 3 bedroom (King, California King, and Two... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 25 October 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 stars Reviewed 23 May 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 stars (43) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    Wow ! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui Wailea, Ekahi Village condo (28D). Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than four minutes.When you... View all property information
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    Wailea, Maui 96753 9532
    5 of 5 stars Reviewed 15 May 2016
    We just got back from staying in 28D and we found ourselves several times saying the condo was better than the website. The owners have done a great job outfitting the condo and...
    5 of 5 stars Reviewed 24 March 2016
    My stay at the Peabody's Condo was a visit to Paradise. The view from every room was stunning. The unit has been recently remodeled and you think you are walking into a brand...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Relax on your lanai, enjoying the radiant blue waters to your west, and the stunning sights of Haleakala to your east. Overlooking the pristine fairway, beyond which the ocean shimmers, you'll find your stay in Grand Champions 75 to be a welcome tropical retreat from all of your worries and cares.... View all property information
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    Wailea, Maui 96753
    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Balcony
    • Ocean Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Relax and Enjoy this spacious and modern one bedroom two bathroom condo with high end remodel. This condo is on the second floor in a two story building so you have amazing vaulted ceilings and no one above you. This is a completely private one bedroom condo with your own private lanai. There are... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 6 August 2015
    We thoroughly enjoyed Kathleen's condo and her hospitality. The beds were comfortable. The condo had just been remodeled and was gorgeous. We could tell a lot of thought and...
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    1 / 13
    4.5 of 5 stars (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • 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 stars Reviewed 21 August 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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    1 / 16
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Wi-Fi
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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
    4 of 5 stars Reviewed 27 May 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 / 41
    5 of 5 stars (23) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Mountain Views
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled in a quiet lower village setting right on the green belt, our Maui home has recently undergone a complete professional remodel. The ceiling has a real Hawaiian feel with beams and matting, we've opened the kitchen to the living room and created two master suites with private bathrooms. The... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 21 May 2016
    We have stayed at Ekahi more than a dozen times and 11F is by far the most thoughtfully designed, equipped, and well-maintained condo we have rented. The rental process was easy...
    5 of 5 stars Reviewed 17 May 2016
    The first impression upon entering this condo was the cleanliness. Everything was sparkling in the Maui sunshine. At the midpoint of our stay we understood why. We were treated to...
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    1 / 18
    4.5 of 5 stars (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    • Grill
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This ground floor, Wailea Ekahi condominium has an ocean view. There is a king bed in the master bedroom and queen sofa sleeper in the living room. Air conditioning in both the bedroom and living room, ceiling fans throughout, portable stereo with CD player, 2 TV’s and DVD player. There are linens,... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 7 May 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 / 20
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Special Spring 2016 Rates - Please ask ! 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 stars (30) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    • 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
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 6 days ago
    Great. Would return. Close to beach. Comfortable beds. Beautiful community. Nice pools. Shopped at costico close by. Great value. Great patio.
    5 of 5 stars Reviewed 16 March 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 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you need for your Maui vacation. We've stocked our... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (21) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Notes from the Owner: Come relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles of pristine beaches, magnificent sunsets and renowned cuisine, Wailea will surely be your ultimate vacation experience! The active vacationer can tee it up on one of five... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 7 August 2012
    With the sunset over the golf course every night, this was a magic place to stay in Maui. We stayed at a resort the week before, but we just wanted some time to ourselves to...
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    1 / 31
    5 of 5 stars (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
    • Air Conditioning
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    • 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 stars Reviewed 23 April 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 stars Reviewed 11 September 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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    Wailea Holiday Rentals

    If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.

    Things to do in Wailea

    Obviously you will be wanting to hit the beach in Hawaii, and there are many from which you can choose, such as Keawakapu Beach, surrounded by golf courses. If you don't want to spend all your time lying on one of the many south-facing beaches but aren't quite brave enough to go and climb a volcano, Wailea has many things to do for all ages, from playing golf and tennis to the inevitable shops and restaurants, all in an incredible Pacific climate. Wailea is fairly sparsely populated, with around 6,000 inhabitants, so you can also have a great time exploring the countryside nearby.

    Renting villas and condos in Wailea

    Wailea Resort is a wonderful place to visit and stay, but its planning is a bit contrived - the Wailea Community Association issue guidelines for new buildings aiming to preserve the island feel of Maui. With the additional aim of low population density, this does mean that prices even for holiday rentals may be higher than in other parts of the Hawaii island chain. But with the scary prices charged by hotels, and the extra flexibility associated with renting your own villa or condo for your family, Wailea holiday rentals still represent fantastic value for money. With air conditioning thankfully coming as virtually standard, and difficult choices of whether you'd prefer views of a volcano, a golf course, or perhaps a beach, it's an idyllic place to enjoy a great family holiday. And if you are looking for a low cost Pacific break, nothing beats buying local produce and cooking it up in your very own kitchen for the week, rather than relying on a hotel's expensive restaurants.