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Holiday Rentals in Wailea

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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 303 Rentals in Wailea
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    Updated Spacious 3 Bdrm. Wailea Ocean View Condo1 / 22
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA1 / 30
    (37)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Wailea Ekahi Ocean View 50A1 / 17
    (19)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just totally remodeled, this stunning split-level 3/3 Maui Hill condo features dramatic ocean views from both levels, and every comfort and convenience. Lives like a residence rather than a condo, with NO common walls and no one above - this unit occupies the entire floor All new furnishings, beds,...
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    Wailea, Maui 96753
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Brand new 2 bedroom beach front at the Mana Kai Maui Resort! On Keawakapu beach!1 / 23
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2018
    This is a wonderful resort, and this particular unit is perhaps the best unit on the entire resort! On the fifth floor or 7 or 8 floors total. Amazing view of the beach and...
    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
    New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei1 / 33
    (1)Excellent
    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
    Reviewed 24 August 2019
    This Ho'olei condo is gorgeous, spacious and well-appointed. The view of the ocean is spectacular, and the smells of the flowers from the lanai are breathtaking! The condo is...
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    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
    5 Star Luxury Condo - Walk to the Beach1 / 35
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 2019
    We thoroughly enjoyed our stay on Maui and it was definitely enhanced by having a wonderful place to live in for just over 2 weeks. The condo is well stocked, clean, across the...
    Reviewed 8 July 2019
    Excellent location, walking distance to beach. The condo is perfectly equipped with everything you need. Lovely furniture and nice view from balcony.Owner is easy to reach and...
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    About this property
    5 Star Property located across from Kihei's favorite beach. 2 roomy bedrooms and 2 bath unit with many high quality, unique upgrades rarely found in a vacation rental: sea turtles inlaid in the porcelain tile flooring, beautiful mulberry flooring leading to and in the upstairs master bedroom, three...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Maui Wailea Townhouse, 2BR, 2.5 Ba, air conditioned, sleeps 8, ocean view1 / 16
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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
    The Perfect Location for a Relaxing Hawaiian Getaway - Grand Champions #1031 / 31
    (8)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2017
    This is the second time I have stayed at this condo, and it was even more impressive than I had remembered! They have an amazing property manager, who takes time to make sure...
    Reviewed 11 August 2017
    We had an amazing time in Maui. Staying at Grand Champions made it that much better. It is beautiful home, clean and nicely decorated, the location is ideal (close to beaches...
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    About this property
    Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a 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, benefit from the warm...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located near the Maui Kamaole's amazing Grotto pool, this elegant and serene condo has been beautifully updated with high-quality furnishings, high-end luxury mattress and bedding, and even all the beach gear you'll need, this immaculate condo is set up for your ultimate Maui adventure. Free...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Grill
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    • Hot Tub
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Grand Champions 121 This gorgeous, bright, airy and quiet ground floor unit features a large bedroom with a comfortable, king-size bed, a living room with a large comfortable sofa, a full kitchen, dining area, 2 full bathrooms, a lanai featuring tropical garden views and a shared pool and...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Spectacular 3rd Row at Ho'olei with Ocean Views1 / 33
    (1)Excellent
    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
    Reviewed 18 August 2018
    This Ho'olei villa was huge, clean and had everything we needed. Our family of 7 had a wonderful time. We could eat and drink whatever and whenever we wanted and spends lots...
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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Ocean Views
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the Top Floor of the preferred building (Bldg. 3) at Maui Vista Resort, this beautifully renovated and decorated condo features a full-on, direct ocean view from the living room and lanai. Everything is new and sparkling from a remodel in October of 2018, done in an upscale, tropical...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched ocean front directly between Kamaole I and Kamaole II Beaches two of Mauis spectacular, postcard swimming and sunning beaches the iconic Royal Mauian is a sun-worshipers dream. Centrally located in the heart of South Kiheis sun culture, the property is one of the few actual ocean front...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculate condo was recently remodeled, and features an elegant, tropical theme that will set the tone for your Maui adventure. Every amenity and convenience has been anticipated and provided for by the Seattle owners, who have furnished their Maui getaway with pride. Located directly across...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Parking
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this contemporary, top-to-bottom remodel with every square inch of the condo sparkling new and live your Maui adventure in consummate style at one of Mauis top-rated condo resorts. Every room was completely remodeled with beautiful new flooring, paint, fixtures, and furnishings from Mauis...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweeping views of the ocean from your living room and extra-large lanai await at this newly remodeled beach retreat, which hosts four guests in consummate, tropical style. Taking its all-new decor theme from the stunning stretch of soft, golden sand at Kamaole Beach III just across the street, your...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Ocean Views
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Arguably the most beautiful unit with the best view on the property, this stunning Penthouse unit was just remodeled from top to bottom. Its a brand-new listing be one of the first to enjoy it! No expense was spared in creating the ultimate vacation rental experience, a 45-second stroll to the...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Featuring a prime location at one of the top-rated vacation condo properties on Maui, this beautifully updated Maui Kamaole luxury condo sits on 23 lush, tropical acres, convenient to the propertys preferred Tropical Oasis pool and close to South Kiheis stunning Kamaole III Beach. Most units here...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Hot Tub
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the third floor of highly desirable Building 5, this stunning condo has been beautifully remodeled in an upscale, elegant Hawaiiana tone. The unit overlooks the tropical courtyard, with great ocean views beyond. Every amenity and guest consideration has been addressed: it's air...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
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    • DVD Player
    • Terrace
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Ekolu is a beautiful 148-unit condominium development in luxurious Wailea, Maui. It is centrally located within a mile of The Shops at Wailea and many elegant restaurants such as Spago, Humble Market and Humuhumu. It is also a few minutes from the championship golf courses of Wailea and...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweeping ocean views from this Penthouse-level, with near instant access to stunning Kamaole III Beach one minute from the front door. Perfectly positioned on the top floor to enjoy the beautiful views. Located amid South Kiheis beach culture, just a few blocks from Wailea, Maui Parkshore is...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Ocean Views
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Featuring a top-floor Penthouse corner location (extra windows, extra light, extra views) and one of the largest footprints of any vacation rental condo in Kihei (1188 square feet), this ocean view unit sleeps six comfortably and serves as the ultimate base for your Maui adventure. The Kamaole...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the ultimate tropical Maui vacation at the highly rated Kamaole Sands Resort, with its lush courtyard, the largest resort pool in South Kihei, and ultimate location a one-minute walk across the street to its warm-water swimming and snorkeling at pristine Kamaole III Beach. This...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean and mountain views from this penthouse level two-bedroom, two-bath 1188 square foot condo in the highly desired building 10. Kamaole Sands sits across the street from Kamaole from Kamaole III Beach Park in South Kihei, Maui. Enjoy the view from your large 166 SF lanai; half covered and half...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the preferred and quietest building at Kihei Akahi (Building D), this ground floor condo is meticulously maintained, and has been nicely updated in a contemporary, tropical tone. Upgraded and fully equipped kitchen features bamboo cabinets, granite counters, and gas range. This cool...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This extra-spacious two-story town-home-styled condo has no common walls and no one above, with a premiere location at the highly-rated Wailea Ekolu. Enjoy panoramic ocean views from Makena and Molokini to the West Maui Mountains, from the lanai and from the inside of the unit as well. Two private,...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mana Kai Maui is Kihei's most exclusive vacation rental resort, with its location on the sand on Keawakapu Beach - and this unit features a prime location in the building, with sweeping views down the south Maui shoreline, to the Wailea resorts. Fabulous snorkeling directly in front of the...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Wi-Fi
    • Balcony
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    • Hot Tub
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overlooking the beautifully manicured tropical courtyard with a view of the brilliant blue ocean just across the street, this elegant condo has been thoroughly updated to second home standards by a very particular owner. Situated in the preferred Building 2 on the second floor of the highly rated...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • Cable/satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience breathtaking, panoramic ocean views from main living area and over-sized lanai of this spacious single level luxury condo, in the heart of Wailea and convenient to world class golf, tennis, restaurants and shopping. Sweeping and unobstructed 180-degree views of Molokini Crater and the...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Ocean Views
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience an upscale Maui vibe from the moment you enter this brand newly remodeled condo, located directly across the street from one of South Kiheis best beaches, Kamaole III. With dramatic ocean views right from your private patio, this location provides immediate access to Mauis warm, pristine...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Maui Kamaole K-108 This spacious ground floor condo features everything you need for a fantastic Maui vacation. The spacious living room is perfect for the whole family to relax and cool off in and watch the curved HDTV after a big beach day. The pool and grill area are just steps from your front...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
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    Pet friendly
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    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
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kamaole Sands 5-304 With a view of the ocean, the surrounding palms, and the community pool below, you'll admire unforgettable sunsets from the lanai of this third-floor condo in Kihei! Enjoy a king-size bed in the master bathroom, a separate updated bathroom near the living room just for the kids,...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    80 5 STAR REVIEWS-GORGEOUS CONTEMPORARY DESIGN/ ZEN GALLERY FEEL/ AVAIL 3/26-4/31 / 25
    (19)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • 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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This top floor, two-story luxury condo showcases expansive ocean views from the living room, kitchen, and extra private oversized lanai. Premium location in one of the top-rated, lowest-density resorts in South Kihei. Located two blocks from Wailea and a short stroll to two of Maui's top-ranked...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Grand Champions 87 Newly and beautifully remodeled from top to bottom, this golf-course-front condo in the heart of Wailea will treat you to sunset views over the ocean and an overwhelming feeling of aloha. Enjoy such thoughtful additions as a brand new central AC system with splits, new...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
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    • Grill
    • Balcony
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island Surf 304 Drop your bags and breathe in the ocean air on your lanai as you start your vacation across from the beach at this Island Surf condo in Maui. Centrally located, this condo boasts an in-unit washer & dryer, AC, powerful ceiling fans, a shared pool, and views that are worthy of going...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pacific Shores A106 This bright and airy, ground floor rental is just what you're looking for! The gorgeous, shared pool and hot tub are ideal for a little fun in the sun! Whether you enjoy your coffee on your private patio, cook up a meal in the updated, full kitchen, or do a little grilling in...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Ekolu is a beautiful 148-unit condominium development in luxurious Wailea, Maui. It is centrally located within a mile of The Shops at Wailea and many elegant restaurants such as Spago, Humble Market and Humuhumu. It is also a few minutes from the championship golf courses of Wailea and...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach. This Maui condo resort location spans 35 lush acres, and offers guests a truly memorable Maui vacation experience. Surrounded by lushly...
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kihei Akahi D-612 In an unbeatable oceanview location, this Maui island vacation rental is perfect for your next Hawaiian getaway. Spend your days on the quiet beach across the street, then enjoy an evening of grilling your favorite tropical meals while you relax poolside. With a private, furnished...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wailea Ekahi is a beautiful 287-unit condominium development in luxurious Wailea. It is centrally located within a mile of The Shops at Wailea and many elegant restaurants such as Spago, Humble Market and Humuhumu. It is also a few minutes from the championship golf courses of Wailea and Makena....
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    Wailea, Maui 96753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Experience one of the most breathtaking views in Maui from this luxurious condominium located at one of the most exclusive resorts in Wailea. Surrounded by world class Polo Beach and Wailea Beach, this condo will immerse you in tropical luxury. Just next door you will find the Fairmont Kealani and...
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    Wailea, Maui 96753
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kihei Akahi D-313 Enjoy cool ocean trade winds and views of the community gardens, the pool, and the Pacific Ocean at this wonderfully positioned condo in Kihei! After a day of fun at the beach across the street, you'll come home to a private lanai with sunset views, air conditioning in the living...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach - 3 min. walk, Remodeled1 / 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
    Wailea Ekahi 7G Luxury Ocean Front S Maui Condo1 / 18
    (37)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2017
    We stayed at this beautiful condo in Wailea for 10 wonderful days. It has everything you may need and more to make your stay relaxing and enjoyable. The condo is beautifully...
    Reviewed 27 February 2017
    We stayed here on our Honeymoon. It was in a perfect location and probably the most beautiful rental we have ever stayed in!! It had everything you could possibly need and want...
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    About this property
    EXCELLENT LOCATION, BEAUTIFUL & PRIVATE OCEAN VIEW! Watch the surf, check out the beach and listen to the rhythm of the waves breaking onto black lava rock. Completely remodeled, refurnished & professionally decorated. Enjoy wonderful ocean, tropical gardens and Haleakala views. A true 'Paradise...
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    Wailea, Maui 96753
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    One-of-a-Kind Maui Getaway!1 / 30
    (7)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 22 July 2019
    Terrific vacation rental with an unbelievable view of Molokini, Lanai, Molokai, and West Maui. I can't imagine a more incredible view in all of Hawaii. The home more than...
    Reviewed 20 February 2019
    The house is a very modern and well kept home with a great infinity pool and outside kitchen overlooking Wailea. We had plenty of space and amenities. What we particularly...
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    About this property
    Created by Owner and Architect Kyron Brimmer, this exceptional home blends traditional and modern Hawaiiana design for a truly One-of-a-Kind Maui Getaway! Float in the infinity edge pool as palm trees sway while soaking up the tropical sunshine. Enjoy the soothing trade winds. Watch whales breach...
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    Wailea, Maui 96753
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    SPECIAL SPRING RATE FOR AN 'ALOHA' OCEAN VIEW AT MAUI KAMAOLE G-2121 / 29
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Hot Tub
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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View the ocean and Haleakala from this beautiful 2br/ba condo fully stocked with everything you'll need for a wonderful vacation. Only 150 yds to the Beach! Located in south Kihei across from 2 of Maui's best water activity beaches and close walking distance to many restaurants, shopping and...
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    Wailea, Maui 96753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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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