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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 / 22
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 square foot villa with large... View all property information
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    Wailea, Maui 96753
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Mountain Views
    • Washer
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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
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    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 / 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 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • DVD Player
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    • Ocean Views
    • Mountain Views
    • Hot Tub
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ocean View, Spacious, Paradise! ~^~^~^~^~^~^~^~^~^~^~^~^~^ Luxurious LARGE two bedroom, two full bath condo in a private, secure beachfront village. This unit has a partial ocean view from the glass-paneled lanai, as well as from the master bedroom and living room, and is just five minutes' stroll... View all property information
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    Wailea, Maui 96753
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Hot Tub
    • Sauna
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Ocean Views
    • Mountain Views
    Suitability
    • 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 / 22
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Mountain Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    This ground floor corner villa at Grand Champions Resort features three bedrooms, two baths, a fully equipped gourmet kitchen, and two lanais. Surrounded by the manicured fairways of Wailea's famed Blue Golf Course and the spectacular grounds of the Wailea Tennis Club, this quiet, well-managed... View all property information
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    Wailea, Maui 96753
    5 of 5 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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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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    About this property
    Spend your vacation at Ho'olei luxury villas at Grand Wailea on Maui! Located just minutes from the world-class Grand Wailea Resort Hotel & Spa on Maui's southern shore, each two-story villa offers a luxurious home in paradise. Every villa has three bedrooms and 3.5 baths with finely appointed... View all property information
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    Wailea, Maui 96753
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    1 / 21
    5 of 5 stars (7) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • Grill
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    • Balcony
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    • Pet-friendly
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    About this property
    Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named with vaulted ceiling, HD TV, DVD, wireless internet and formal dining area. Tropical blue and turquoise colors convey a serene ambiance comparable to the pristine... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 24 July 2014
    Our vacation rental was clean, spacious, quiet and most importantly, had great views. If you are looking for a great family rental on your vacation, I highly recommend Ho'Olei!
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    1 / 16
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Waterfront
    • Shared Outdoor Pool...
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    • Grill
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    • x
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    About this property
    Spring 2016 Specials - please inquire! Wailea Ekahi 3C is a charming one bedroom, one bath, first floor garden view condo. It is a great choice for singles or couples wanting a reasonably priced condo close to the beach. The private garden setting is great for relaxing and enjoying the soft sands... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 5 November 2011
    We love staying at Ekahi Village condos. We have stayed here multiple times, this last time in 3C. What we love most is that there are no surprises, everything is exactly as...
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    1 / 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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    • Waterfront
    • Air Conditioning
    • Patio
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 and 1/2 baths, 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 / 24
    5 of 5 stars (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    Here's is your chance to experience this gorgeous condo at the Palms at Wailea. Newly renovated fully air conditioned, Charcoal grey bamboo floors, Whotel Pillow top Cal king mattress including the WHotel feather bed that makes you feel like your floating. There is also 2 flat screen TV's and the... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 27 May 2016
    We loved our stay at Lawrence's condo. The condo is beautifully remodeled and well-equipped. It is located perfectly between the beaches of Wailea and the cute town of Kihei...
    5 of 5 stars Reviewed 13 December 2015
    1st off I have to say... I can't wait to go back to this space!!! My partner and I stayed In Lawrence's beautiful condo! Tasteful and stylish with its decor, with its...
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    1 / 14
    4 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
    • DVD Player
    • Internet Access
    • Terrace
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Special Spring 2016 Rates. Please Ask ! A spacious two bedroom two bath condominium in beautiful Wailea. A partial ocean view, barbeque grill and comfortable lanai furniture to enjoy while relaxing in tropical breezes. The kitchen is well equipped, has granite counters and modern appliances.The... View all property information
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    Wailea, Maui 96753
    1 / 17
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Special Spring 2016 Rates - Please ask ! Grand Champions #35 is an inviting third floor, two bedroom, two bath, Ocean View condo. The living room has sofa and love seat, A/C, Large Flat Screen TV, Blu-Ray player and a Wireless Bluetooth Speaker. The newly updated kitchen has granite counters, new... View all property information
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    Wailea, Maui 96753
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • DVD Player
    • Patio
    • Air Conditioning
    • Hot Tub
    • Grill
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Features of our four bedroom three bath villa include: Over 3000 sq ft of living space, sleep up to 8 guests Two separate master suites with large walk in closets Two bedrooms can have either two twins or king bed Dramatic Great Room with oversized sofa with surround sound system Waterworks... View all property information
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    Wailea, Maui 96753
    1 / 19
    5 of 5 stars (7) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Relax in this spectacular three bedroom deluxe accommodation. Beautifully decorated, many exquisite art pieces and special touches create a warm inviting atmosphere. The living room features state of the art entertainment center with 50" HD TV, DVD, Ipod dock, high speed and wireless internet. The... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 9 August 2015
    I cannot express enough how wonderful our two week vacation was in Maui. Our family of six (with four teens) built memories that will last a lifetime. Ho'olei was the PERFECT...
    5 of 5 stars Reviewed 12 August 2011
    We stayed for a week as a young family of four. The location in the complex was ideal as we could easily walk to *and* see the pool--many units offer one but not the other. This...
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Balcony
    • Grill
    • Ocean Views
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ekolu #1108. Two-bedroom, two bath Ekolu condo with breathtaking ocean view! 180 degrees spanning from West Maui, to Lanai, across Maalaea Bay, above the Wailea Resorts, past Molokini, and even beyond the island of Kahoolawe. Some condos provide fantastic sunsets part of the year, this one... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 12 November 2011
    We booked this condo for 8 days. It was everything that had been described to us and more. The view was fantastic. Everything we needed was there, all we had to bring was our food...
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    1 / 27
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Balcony
    • DVD Player
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    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. Our condo has a terrific layout with the bedrooms being on opposite sides of the condo. Each has its own private washroom, flat screen TV and... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 18 September 2013
    Once again, I loved everything about this condo. Beautiful first class furnishings, close to wonderful beaches in Wailea & Makena, & great shopping. The extra touches like the...
    5 of 5 stars Reviewed 21 November 2012
    The condo was beautifully furnished. We appreciated all the extras that made this stay so relaxing like the Tommy Bahama beach chairs, boogie boards, beach towels, & beach...
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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
    • Wi-Fi
    • Air Conditioning
    • 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 / 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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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • 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 / 23
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Patio
    • Shared Outdoor Pool...
    • Washer
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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
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    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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    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
    • Washer
    • 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 1 September 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 24 July 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 / 22
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Wi-Fi
    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Special Spring 2016 Rates. Please ask ! Relax and spread out in more than 3300 interior feet of custom home with designer furnishings. The tropically furnished living area with vaulted ceiling offers HD TV, DVD, IPod dock, and wireless internet, all in an intimate yet spacious room. The gourmet... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 9 January 2016
    Our family of seven thoroughly enjoyed our vacation here! The place was spacious, comfortable, clean and exactly as pictured online. The wireless internet worked great (which I...
    5 of 5 stars Reviewed 2 March 2015
    We rented this Villa to vacation with our adult children, son, daughter and son in law for a week in February. It was exactly as I pictured it online and was lovely, very clean (I...
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    1 / 20
    5 of 5 stars (24) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Balcony
    • Mountain Views
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our second story 3 bedroom villa with 1383 feet, is located in the beautiful Grand Champion Complex, located in the resort area of Wailea. Our corner villa offers a panoramic view of the West Maui Mountains as well as the ocean. The villa also overlooks the seventh farway of the Wailea Blue... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 4 weeks ago
    We had a fabulous time! Tony and Bev have taken well care of the home. Great advice on places to go and places to eat if you don't want to cook. Short walking distance to beach...
    5 of 5 stars Reviewed 16 June 2014
    This is one of the best condos we have ever had the pleasure to stay in while visiting Maui. I read numerous reviews which had stated how well stocked the condo was. I would...
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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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    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wow ! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui Wailea, Ekahi Village condo (28D). Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than four minutes.When you... View all property information
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    Wailea, Maui 96753 9532
    5 of 5 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 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool...
    • Internet Access
    • Balcony
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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 / 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 / 14
    5 of 5 stars (21) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Parking
    • Wi-Fi
    • Washer
    • DVD Player
    • Patio
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • DVD Player
    • Washer
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
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    Wailea, Maui 96753
    5 of 5 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 / 23
    5 of 5 stars (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Grill
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful three bedrooms, two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated in the fall of 2010 with granite throughout, stainless steel appliances, new carpet, paint and furniture. The living area is a large open floor plan with ceiling fans and... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 10 October 2014
    My friends an i find the Grand Champions condos to be quiet an peaceful. It's close to three great golf courses and several good restaurants. We live in Honolulu, where we have...
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    1 / 19
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Special Spring 2016 Rates! Please inquire. Grand Champions 163 is a delightful ground floor two bedroom tiled throughout with the exception of the bedrooms. Beautiful, Kitchen and Vanity Cabinets with Granite Counter tops. The Living room has a cozy sectional sofa, flat screen TV, DVD, wireless... View all property information
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    Wailea, Maui 96753
    1 / 21
    5 of 5 stars (14) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
    • Wi-Fi
    • Waterfront
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 29
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Outdoor...
    • Washer
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Note: *** Our calendar is always up to date. Low Season Rate (Apr 16 - Dec 15) $395.00 per night High Season Rate (Dec 16 - Apr 15) $450.00 per night Are you looking for a quiet peaceful alternative vacation experience away from the hotel zone but minutes away from South Maui's best beaches,... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 27 July 2014
    We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
    5 of 5 stars Reviewed 9 July 2014
    The wife and I and are 3 children (9, 9 and 3) stayed here for 8 nights! Looked at many homes in Maui and man did I nail it with this one! Perfect location, perfect owners...
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    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Satellite TV
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Please ask us about our Spring 2016 Specials. Grand Champions 186 is located on the second floor and overlooks one of the 2 pools on property. Featuring a modern Hawaiian theme throughout. The living room has a large High Definition TV with DVD, high speed and wireless internet, comfy sectional... View all property information
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    Wailea, Maui 96753
    1 / 35
    5 of 5 stars (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Mountain Views
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Porch
    • Grill
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Experience the REAL 'Old Hawaii' in our private unattached HOUSE, NOT a noisy condo, ohana or part of a house. LEASE JUNE 1 - NOV 30 at $3,999/mo. You will feel the ocean breeze, see it and clearly HEAR the ocean on this culdesac. From deck to ocean is about 200 yards in which you can walk to the... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 5 April 2016
    My wife and I spent 10 days here and had a blast. It's located very close to the beach where you can hear the waves. The landscapping is beautiful and is grown up to keep you...
    5 of 5 stars Reviewed 15 May 2014
    For me as an artist, staying at Sam and Rebecca's cottage, inspired a number of drawings, photographs and watercolors. My husband was able to disconnect from electronic media and...
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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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    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool...
    • Parking
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    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious living room opens to the Lanai, where there is ample space for stretching out and relaxing in the sun, barbecuing on your own private grill, or admiring the tropical grounds of The Palms at Wailea.... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 16 February 2015
    This is a terrific location for a visit to South Maui. We used the whale watch rafts from the Kehei ramp. Close to Safeway, beaches with full service and beach parking. Loved...
    4 of 5 stars Reviewed 3 August 2014
    We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
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    1 / 20
    5 of 5 stars (37) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade has been completed resulting in a home away from home with only highest quality finishes.... View all property information
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    Wailea, Maui 96753
    4 of 5 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 / 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...
    • Air Conditioning
    • Washer
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a recently renovated luxury first floor condo in Wailea's premier Grand Champions Villas. Our home is unit #103 on the east side of the complex. Spend your vacation enjoying this 1 bedroom, 2 bath unit that provides ample space to spread out,... View all property information
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    Wailea, Maui 96753
    4 of 5 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Children's Pool
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Satellite TV
    • Hot Tub
    • Parking
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    • DVD Player
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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 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Please ask for our Spring 2016 rates ! Wailea Ekahi 27B offers Ocean views from the upstairs master bedroom Living area and Lanai. The master bedroom has a king bed, ocean view and en-suite bath. The guest bedroom has a new Queen bed and beautiful garden view. Both bedrooms have air conditioning... View all property information
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    Wailea, Maui 96753
    1 / 77
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Patio
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    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    Azure Azul M212 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October 20, 2015. In May... View all property information
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    Wailea, Maui 96753
    1 / 64
    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • DVD Player
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    • Private Outdoor...
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    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    2-5 Bedroom, on the sand in front of the Fairmont Kea Lani in Wailea / Makena Maui, Hawaii. Features: Beach Front - On the Sand! Snorkeling. Central Air conditioning We have correct HOTEL ZONING for Maui vacation rentals Sleeps 6 Two elevators By Owner Beachfront Pool and Spa On the Wailea... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 4 weeks ago
    Pictures don't do it justice. This is a corner condo off one of the best beaches in Maui. Great beach for body surfing, great beach for swimming, also great area for snorkeling...
    5 of 5 stars Reviewed 30 November 2014
    The highlight of the stay for me was the back lanai. It was large enough for me to do my yoga in the morning and it had a wonderful breeze and an incredible view! The four of...
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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
    • 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 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 / 61
    5 of 5 stars (14) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    <b>Island Oasis M111 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards!</b> The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October 20, 2015.... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 17 January 2012
    Spending our 35th anniversary here, in the beautiful Island Oasis Villa, could not have been more perfect. The owners of this villa know what they’re doing. Heavenly beds...
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    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    MAY SPECIAL May 15-21st only $450/night plus tax May 28th - June 4th only $450/night plus tax Come stay with us here in sunny south Maui at our beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around... View all property information
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    Wailea, Maui 96753
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Parking
    • Satellite TV
    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Grand Champions 123 is located in a quiet setting in Wailea. Large green belts, manicured grounds and wide golf course fairways abound. To the east, views of Mt. Haleakala, the world’s largest dormant volcano. To the west, the sparkling blue Pacific Ocean. A quieter, more peaceful resort, this... View all property information
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    Wailea, Maui 96753
    1 / 16
    3 of 5 stars (2) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautifully decorated three bedroom two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated the summer of 2011 with granite throughout, stainless appliances, new carpet, paint and furniture. The living area is an open floor plan with ceiling fans and... View all property information
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    Wailea, Maui 96753
    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.