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Holiday Rentals in Wailea

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    All 219 Rentals in Wailea
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    Summer Sale only $175 night - Request at booking1 / 43
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    New Listing Budget Vacation! Kihei Akahi C-6161 / 24
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Wailea Ekahi Ocean View 50A1 / 17
    (13)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Wailea Ehaki 20F - 2min Walk to Beach, Ocean Views1 / 36
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
    • Housekeeping Included
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    Me and my family had a wonderful visit at Ekahi 20F! The view was beautiful and th beach was so close! The condo was amazing and we had so much fun hanging out and using all of...
    Reviewed 18 August 2016
    This condo worked out great for our family of four. I do a lot of research when booking a rental, and I know what I want. So, the best outcome is when the place turns out to be...
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    About this property
    Wailea Ekahi 20F is a 2 bedroom unit featuring panoramic ocean views, a great, quiet location with a short, 2 minute walk to Keawakapu Beach. As new owners, we welcome you to enjoy our condo and all that it has to offer! Wailea Ekahi Village is a premier ocean front condominium community located...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wailea Ocean View, 2Bed, 2Bath Beautiful Update1 / 25
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Children's Pool
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2017
    This villa was in a very nice condo development (Grand Champions), only minutes away from several of the best beaches on Maui, as well as convenient to shopping and dining. The...
    Reviewed 24 May 2017
    The condo was very nice - not the most luxurious I've ever stayed in but very good. Pics were accurate. Well stocked dishes/utensils/cookware. 4 nice beach chairs/ large beach...
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    About this property
    Live luxuriously while on vacation! Beautiful Hawaiian art, travertine floors, granite countertops, tall bath vanities, and elegant new furniture make this condo a place of comfort and serenity. The two bedrooms are private, each with an en suite bathroom. The master bedroom offers a California...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Maui Wailea Townhouse, 2BR, 2.5 Ba, air conditioned, sleeps 8, ocean view1 / 15
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2015
    We were very pleased with our stay. Condo fully stocked. Beautiful views. Convenient location. Comfortable and roomy. Would stay here again.
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    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...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful, Renovated, Hale Kamaole 159 now available! Walk to Kamaole III Beach!1 / 24
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hale Kamaole 159 is ready for your ideal Maui beach vacation! It is a newly renovated, exceptionally clean, 1 bedroom, 1 bath condo located in beautiful Hale Kamaole, right across from Kamaole Beach Park III, where you can enjoy sunbathing, snorkeling, clear blue water, and swimming with turtles...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    SPRING SPECIAL $189 a nt 4/24-4/28 5 STAR reviews  GORGEOUS Palms at Wailea Gem1 / 25
    (19)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2018
    Lawrence's condo was so beautiful, yet comfortable! Beautiful photography artwork on the walls, gorgeous dark bamboo flooring, and such a comfortable king-size bed, made it...
    Reviewed 26 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...
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    About this property
    Here's is your chance to experience this gorgeous condo at the Palms at Wailea. Newly renovated fully air conditioned, Charcoal grey bamboo floors, Whotel Pillow top Cal king mattress including the WHotel feather bed that makes you feel like your floating. There is also 2 flat screen TV's and the...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    SPECIAL $150/nt,8/1-10,8/20-31;$200/nt9/1-14 Wailea Ekahi 33ALuxury Beach Resort1 / 24
    (14)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Housekeeping Included
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    LUXURY FOR LESS! Best value in Hoolei Wailea!1 / 24
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
    • DVD Player
    • Sauna
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Highly recommend . Beautiful house , it's a good place for a few family to stay , if you like to save money,and cook is the one you should rent
    Reviewed 22 June 2017
    This villa in Ho'olei was beautiful--wonderful location with easy access to restaurants, shopping, and of course, the beach! The pool was relaxing, not crowded at all. Some of...
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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...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful Modern Wailea!  From $1501 / 25
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2017
    It was very nice staying at a condo, where you could walk to the beach, do slides, do yoga, and see turtles, what an enjoysble week!
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    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! Experience island life in our luxury, spacious, one bedroom. This rental is offered to you directly from a local couple intent on providing you with the ultimate vacation rental experience - clean,...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a great 2 bedroom and 2 full bath unit for 'the island explorer' and guests who come to enjoy the outdoors of Hawaii with all its beaches, waterfalls, tropical forests or pineapple fields and Luaus . This condo has everything you might need on your vacation< (yes even a washer and dryer)...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Family Beach Headquarters: Maui Banyan 2 BR Condo at Beach, Sleeps 4-81 / 14
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Ocean Views
    • Hot Tub
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    This condo was directly across from the beach. Traveling with younger children (3 & 5) this made daily activities very easy because it was a quick walk to the beach where...
    Reviewed 11 November 2016
    There were 7 adults why stayed in this place. It was dated, but clean and lovely! Would stay again!!
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    About this property
    This two-bedroom condo unit was awarded a Certificate of Excellence from TripAdvisor in 2017 for service quality and customer satisfaction. Best for families, such as parents with up to 6 children, for a combination of grandparents, parents and kids, or for two couples vacationing together. If...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! Experience island life in our luxurious, spacious, one-bedroom Condo at Wailea Grand Champion Villas. Steve and Tamara are intent on providing you with the ultimate vacation rental experience - clean,...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Brand new 2 bedroom beach front at the Mana Kai Maui Resort! On Keawakapu beach!1 / 23
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2017
    We loved seeing a whale breach in a perfect arch way out of the water at sunset directly out from our balcony! We spent many hours on our balcony eating and enjoying the beach...
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    About this property
    This amazing newly renovated two bedroom condo has breathtaking ocean views, brand-new everything including appliances and top of the line luxury mattresses and bedding! Located on the fifth floor giving you stellar ocean views. The property is oceanfront situated on one of the most beautiful...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming Private Studio!  From $1151 / 18
    (12)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Hot Tub
    • Washer
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 December 2016
    Steve and Tamara's studio was just what I was looking for. A gated community central to everything in Wailea area. Nicely appointed studio, includes washer/dryer on lanai. Large...
    Reviewed 30 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...
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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...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully furnished newly remodeled two bedroom, two bath luxury condo located in Maui Kamaole complex; Kihei's newest first class resort property. Nestled in the center of the sunny South Maui coast, Maui Kamaole is located across the street from famed Kamaole III Beach where you can enjoy...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    SPECIAL SUMMER RATE FOR AN 'ALOHA' OCEAN VIEW AT MAUI KAMAOLE G-2121 / 14
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    We have had the opportunity to stay at Maui Kamaole several times and unit G-212 is absolutely great. We viewed whales every day from the balcony. We enjoyed Kam III beach...
    Reviewed 12 March 2018
    We have rented this condo on several occasions and it is always updated and clean. It has a fully equipped kitchen, beach towels, and beach chairs, most any thing you need for...
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    About this property
    Maui Kamaole G-212 is a spacious and elegantly appointed condo with an incredible 'Aloha' oceanfront view and a great location near all of the spectacular south Maui beaches. From the lanai, you look out on the beautiful Kamaole Beach III--a fabulous swimming, boogie boarding, and snorkeling beach...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BRAND NEW, Remodeled 3-Bedroom, Huge Ocean Views, Across From Great Beach Just totally remodeled, this stunning split-level 3/3 Maui Hill condo features dramatic ocean views from both levels, and every comfort and convenience. All new furnishings, beds, appliances, and everything else are brand...
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    Wailea, Maui 96753
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Outstanding Luxury Condo for Couples in Paradise - Ocean and Beacfront1 / 74
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Waterfront
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2017
    Good location to many activities and restaurants. Clean and well supplied with anemities. Beach and pool are somewhat difficult to find.
    Reviewed 23 January 2017
    This condo was great for location and proximity to good walking in Wailea. The pool and beach area was amazing. The Barbecue facilities were at the opposite side of the...
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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+...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View! View! View! How about sipping the gourmet coffee while enjoying the ocean view, listening the bird chirping? How about having the sunset dinner at the lanai with BBQ meal or taking the nap on the Chaise Lounge chair at the lanai when the ocean breeze comforts you? Our condo, 51E located in...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Hot Tub
    • Sauna
    • Ocean Views
    • Mountain Views
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax and enjoy your stay at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui. Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean views from both upper and lower...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax and enjoy the good life at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui. Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean views from both upper and...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Patio
    • Air Conditioning
    • Hot Tub
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Summary Exceptional ocean views and location. The unit was recently remodeled from top to bottom. Well furnished, plenty of extras like a full inventory of snorkel gear, boogie boards and other beach supplies make your stay extra convenient and economical. Clean and well maintained. Location The...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    One-of-a-Kind Maui Getaway1 / 28
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Mountain Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    As many have said, the Butterfly House is a stunning getaway! The home provided lots of room for my wife, our three kids and their mates, to have privacy. but was also perfect...
    Reviewed 28 March 2017
    Our family booked this home after much time searching various websites for something that would fit our needs. We were a group of 4 adult couples and one toddler looking for...
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    About this property
    This One-of-a-Kind Maui Getaway is just the vacation destination you have been dreaming of! Owner and architect Kyron Brimmer, designed this unique and modern 4 bedroom, 4 bath Hawaiian style home with the guest in mind. From pencil sketch to sustainable masterpiece, it captures Maui’s tropical...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Children's Pool
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stop dreaming about it--make your perfect Maui vacation a reality today. Lovingly cared for, very clean. Our one bedroom one bath Unit is ideal for honeymooners and any couple that wants to get away from it all. From this incredible home base with ocean views you can venture out into the tropical...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA1 / 24
    (34)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Washer
    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This was by far the best and most comfortable accommodations we've ever stayed at on Maui over multiple prior vacations. The bungalow is a perfect size for a couple to use, and...
    Reviewed 8 March 2018
    Perfect cottage for two to enjoy Maui away from the crowds. Close to all the beaches to get a morning run or snorkel in. well kept clean cottage with all the amenities. Both...
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    About this property
    This is a designer upgraded one bedroom cottage with stunning ocean views. Designer appointments throughout, including gourmet kitchen with beautiful granite counters and top of the line appliances, designer bath with custom tile work, tropical Asian hardwood furnishings, and tasteful local art and...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Beautiful Ocean View 2BR/2Bath1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2016
    This is the perfect place to stay while exploring Maui. The Condo is in a superb landscaped setting and is fully equiped with everything that you are likely to need. If you read...
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    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...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sweeping Ocean Views; Private High End Condo!1 / 22
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
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    • Ocean Views
    • Patio
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2017
    We LOVE Maui and while we've only stayed in West Maui, this was the first time we stayed in South Maui and this is definitely a Wailea...wow! So many beaches to choose and only...
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    About this property
    Unit: Wailea Ekolu 507 | Maui Guidebook Summary Sweeping ocean and breathtaking neighbor island views from the living, dining, kitchen, bedroom and both lanais. Private ground floor corner location. Minutes from the very best beaches in Maui. Minutes from both luxury and down to earth shopping and...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    WAILEA ELUA, #2107*1 / 16
    (7)Excellent
    2 Bedrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed 26 October 2014
    We stayed at Wailea Elua 2107 for a week in October. The view from the front lanai is outstanding and the rear lanai is very private. We used the barbecue once and it worked...
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    About this property
    A Note From the Owner: You will love the extra space in this remodeled supersized two-bedroom, two-bath Elua condo. With nearly 300 square feet more than the typical Elua two-bedroom unit, you can spread out, relax and truly enjoy your stay in paradise. Our large lanai, living room and master...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Waterfront
    • Ocean Views
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    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unit: Beachfront Bliss | Maui Guidebook Summary Direct beachfront unit in very small (12 unit total) condo building. Unit 6 is an end unit, tucked away on the quiet Northern side of the building for the most privacy. This is the way it used to be before Kihei was developed; Kamaole One is an...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ho'olei at Grand Wailea - Deluxe Ocean View1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    We stayed in this condo directly over the private pool. We had three couples and a 14 month old and the space was perfect! The location is great, 10 min walking distance to...
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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...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    QUIET PRIVACY IN PARADISE This is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations in the property. Often the only sound you will hear is the waves crashing on the nearby beaches. The Palms at Wailea is one of the upscale...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Washer
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-2464-04 Wailea Seashore Suite K507 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler's Readers'...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Updated Spacious 3 Bdrm. Wailea Ocean View Condo1 / 22
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2018
    We had a fantastic 2 weeks at the condo. The place is reasonably quiet and has everything you need. It is clean, nice and functional. There are a few things that could be...
    Reviewed 31 October 2017
    My husband, 11-year old daughter and I stayed in this condo along with another family with an 11-year old daughter. This unit was clean, spacious and comfortable. The lanai had...
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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...
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    Wailea, Maui 96753
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Hawaiian Themed Pacific Shores condo has all the bells and whistles and more. Central Air, granite counter tops, beautiful travertine flooring throughout, top of the line appliances, and Bosch washer dryer complement the completely upgraded remodel. There are two Tropical furnished bedrooms,...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Mountain Views
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Palms at Wailea condo complex is one of the most elegant developments in the exclusive and breathtaking resort community of Wailea, Maui. Our condo (Unit #1603) was custom remodeled, designed, and decorated as our personal home, hence it is exquisitely upgraded and superior to typical rentals....
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Regal Mandalay M511 Wailea Beach Villas1 / 50
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2013
    We had a wonderful time staying here. Tropical Villa Vacations does such a great job of taking care of the details. We loved the condo. So much so we had a hard time getting...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-6208-01 Regal Mandalay M511 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler's Readers' Choice...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy our Paradise in Maui only steps away from the best beach on the island! We are also in the heart of Kihei within walking distance of fantastic restaurants with incredible happy hours, grocery stores, shopping, and a community park. Fall in love with our beautiful pool, hot tub, and BBQ...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, Sleeps 4
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    SUMMER 2018 AVAIL PEACEFUL 2BD2/BA REMODELED GRAND CHAMPION in Upscale WAILEA,1 / 23
    (17)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2015
    Stayed here with my husband, toddler and my parents - and it was perfect. The location is right by beaches, shops and restaurants. Also, there are boogie boards, snorkeling...
    Reviewed 7 November 2011
    The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea...
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    About this property
    Relax in the luxury and convenience of being in a world class resort, but enjoy the privacy and beauty of our fabulous 2 bd/2ba ground floor 'home away from home' that fronts the 7th Fairway of the famed Wailea Blue Course. Our spacious 1100 sq ft. unit has a tropical decor with world-class art...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Floral Gardens Villa G102 Wailea Beach Villas1 / 50
    (9)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2015
    My husband and I, along with our baby stayed in this luxury unit in November. The unit has fabulous access to outside lanai's and grass areas. The kitchen was equipped as if it...
    Reviewed 31 October 2013
    Very spacious, perfect for a family. This villa is finished with high quality furniture/appliances etc. it had everything you need and more! the property is secure, quiet and...
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    About this property
    State of Hawaii Transient Accommodations Tax License #TA-*******-1168-01 Floral Gardens Pool Villa G102 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler's...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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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...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Palms at Wailea Unit #2305  Quiet and Very Private!1 / 31
    (15)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Hot Tub
    • Washer
    • Cable/satellite TV
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 December 2016
    The staff were so helpful and even booked our Hana Road excursions for uswe were picked up at bought back no worriesThe pool was great The gardens were beautiful It was a...
    Reviewed 24 November 2013
    I helped my sister and brothers find these condos for our stay in Maui. It was shocking to our entire extended family how large and nice these condos are at the Palms of Wailea...
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    About this property
    We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book 'Maui Revealed' and their website. These properties were chosen because of their superior quality and great rates! The fabulous Keawakapu Beach is just a short 10 minute stroll...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua Beaches are just a 10 minute stroll down the hill from...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • DVD Player
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    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful two level residential home located in South Kihei, Maui. The 3 larger bedrooms have their own private bathrooms. The 2 smaller bedrooms share the 4th guest bathroom. 2 living rooms. 2 car garage. This is South Kihei's newest vacation rental offering. Fully furnished with all the...
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    Wailea, Maui 96753
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Wailea Ekahi 11f:  Ocean View/Remodel 2 BR Condo1 / 21
    (26)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 October 2016
    This condo is beautiful, fully equipped and in a great location. Has a great layout with the bedrooms on opposite sides of the condo. Traveled with another couple so the...
    Reviewed 2 August 2016
    Probably one of the nicest vacation rentals we have experienced. Every amenityis provided from the kitchen appliances to the comfy beds and linens. A spectacular ocean view...
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    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...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sea Breeze Suite J405 at Wailea Beach Villas1 / 50
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2017
    My wife and I along with our 2 sons and their wives, just returned from a week at Wailea Beach Villas J405. From the moment I first contacted Tropical Villa Vacations all the...
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    State of Hawaii Transient Accommodations Tax License #TA-*******-7632-01 Sea Breeze Suite J405 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor's 2016 Travelers' Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler's Readers' Choice...
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    Wailea, Maui 96753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beachfront at Polo Beach Club Wailea-Makena Maui1 / 64
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2016
    All units at Polo Beach Club are not created equally. Our unit, 103, was ideally located. It is on the ground floor but away from the hotel beach bath so there were no privacy...
    Reviewed 30 June 2016
    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...
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    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 Beach...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!1 / 30
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2016
    I took my 94 years old mother to Maui for a family wedding, we loved the condo from the minute we entered, it's spacious and clean, the balcony is perfect for having breakfast...
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    About this property
    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming pools, sundecks, spa tubs, restrooms, showers and...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1
    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.

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