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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 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 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 April 20, 2015
    The condo was spacious, clean and homely. They had everything we needed and the complex was well maintained. very close to Wailea town centre and 15 min walk to resort area. BBQ...
    4 of 5 stars Reviewed December 21, 2013
    We were a group of 6 adults and one toddler and we felt totally at home here and would definitely recommend this condo our friends. Set in an amazing area with world class...
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    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 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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    5 of 5 stars (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    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 May 21, 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 March 1, 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 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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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 July 16, 2014
    Very well appointed unit and beautifully maintained grounds. Went over for my niece's wedding. We had a pre-wedding function with 15 people and everything had we needed...
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    1 / 18
    5 of 5 stars (34) Excellent
    1 Bedroom, 3 Bathrooms, Sleeps 3 | Quick View
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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 February 19, 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 July 26, 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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    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
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    1 / 17
    5 of 5 stars (4) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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 November 14, 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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    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
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    Wailea, Maui 96753
    4 of 5 stars 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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 October 11, 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 August 6, 2014
    We stayed for five days in July with 2 children and 2 adults. The unit was exactly as advertised and had everything and more that we needed during our stay. The view from lanai...
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    1 / 67
    4 of 5 stars (13) Very good
    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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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 / 74
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
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    Wailea, Maui 96753
    5 of 5 stars Reviewed September 15, 2014
    I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    • Children's Pool
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    • Pet-friendly
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    • x
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    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
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    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 August 12, 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 July 7, 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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    • x
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    About this property
    This condominium home has been beautifully upgraded throughout and boasts a newly remodeled kitchen, dining room and living room. Summer 2014 new carpet was added throughout and new living room furniture greets you. The comfortable bedroom has a king bed and en-suite bathroom. There is free... View all property information
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    Wailea, Maui 96753
    1 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    About this property
    Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed July 13, 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
    5 of 5 stars Reviewed March 2, 2015
    This is a spacious condo with all the amenities you'd want for your vacation -- including a washer and dryer inside the condo and a full patio with BBQ. The setting is beautiful...
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    1 / 14
    5 of 5 stars (21) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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 October 1, 2013
    Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
    5 of 5 stars Reviewed September 29, 2012
    We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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    1 / 26
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed August 30, 2015
    This spacious studio was perfect for my needs. it was super comfortable and very very clean and there were little touches of extras like the chips and Karens bread in the...
    5 of 5 stars Reviewed May 3, 2015
    I loved this studio. It was very nice space with a deck. It has a stackable washer/dryer. The bed was super comfortable and owners were responsive to my needs. At the time I was...
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    1 / 35
    5 of 5 stars (2) 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
    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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    • x
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    • 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 October 26, 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 December 16, 2013
    My wife and I stayed in unit 29 at the Grande Champions Golf Villas for two weeks in December, 2013. The property manager Kathleen was fantastic to deal with and responded...
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    1 / 20
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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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 September 12, 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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    • x
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    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 November 26, 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 August 11, 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 / 16
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 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 / 24
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed May 26, 2015
    This is a great condo. We were little unsure because it had no reviews but we are very happy that we booked it. It is renovated, with 2 bathrooms (each has a toilette as well...
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    1 / 21
    5 of 5 stars (14) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
    • Wi-Fi
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    • Mountain Views
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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 September 13, 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 September 10, 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
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    • Shared Yard
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 October 26, 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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    • Hot Tub
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    • Waterfront
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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 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 stars Reviewed February 25, 2015
    I was told about this condo in Australia and could not believe what I was told...then I arrived there and it was beyond what I could have imagined! The condo is fitted out...
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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
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    • x
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    • 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 August 24, 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
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    • Balcony
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    • 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
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    • 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 September 15, 2015
    We stayed at Wailea Ekahi in unit 35B in October and really really enjoyed it. . A favourite happy hour spot was the upper balcony. We loved the ground floor patio and ate our...
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    1 / 58
    5 of 5 stars (7) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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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 October 25, 2015
    Once entering the property which is quite secure, and meeting the friendly and helpful owner, you are taken through a wonderful tropical and well maintained garden around a...
    5 of 5 stars Reviewed May 23, 2015
    When I was planning our family vacation for my wife and 2 adult sons, I spent countless hours researching, talking to friends, etc. As I am a supporter of Tripadvisor, I also...
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    1 / 19
    5 of 5 stars (43) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Satellite TV
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    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 stars Reviewed May 15, 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 March 23, 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
    • ?
    • Smoking allowed
    • 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
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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 August 5, 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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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    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 August 21, 2014
    A very well equipped condo with starter pack of coffee (essential) and other pantry basics. The condo also included new beach towels, decent beach chairs, umbrella, beach mats...
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    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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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 May 26, 2012
    We stayed in this corner condo unit with views of Chang's beach and the southern coast of Maui. The expansive view from the balcony (glass all around) was the best part....we've...
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    • Grill
    • Mountain Views
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    • 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 May 20, 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 May 16, 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
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    • Air Conditioning
    • Balcony
    • Waterfront
    • Grill
    • Shared Outdoor Pool...
    • 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 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • Ocean Views
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    • 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
    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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    • Satellite TV
    • Balcony
    Suitability
    • 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
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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 stars Reviewed 5 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 March 15, 2016
    This rental is fantastic, my wife and my 2 year old went in February. Not only was the rental a great space, with nice appliances (and the sharpest chef knife I've ever had in a...
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    1 / 16
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • 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
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    • x
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    • 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 August 6, 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
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool...
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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 April 23, 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 stars Reviewed September 10, 2013
    I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
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    1 / 28
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Hot Tub
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    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our beautifully renovated spacious 2 bedroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. The large air conditioned Master Bedroom features a king-size bed with high end linens and a large flat screen HDTV. There is also an iPod/iPhone charger and... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed August 31, 2015
    This 2 bedroom condominium has great updates with modern kitchen and bathroom facilities.Master shower is large 2 head walk in room. Washer and dryer on the lanai is a great...
    5 of 5 stars Reviewed July 23, 2014
    This home is absolutely everything you are looking for when staying in Maui. It has it all, location, privacy, amenities, comfort, security stay at what is considered an upscale...
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    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    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 large flat screen TV, DVD player, comfortable sofas, high speed and... View all property information
    Location Information
    Wailea, Maui 96753
    Wailea Vacation Rentals

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

    A Wailea Vacation

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

    Family-Friendly Wailea

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