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Holiday Rentals and Apartments Wailea, HI

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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 25
    5 of 5 bubbles (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    About this property
    SUMMER SPECIAL: Stay 2 weeks in June/July for only $175/night. Simply request the special rate when you inquire. If you love to swim in the ocean, if you have kids who like to play in the sand and go wading, if you want to stroll on a beach holding hands as the sun sets, then our well-equipped,... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 10 November 2016
    There were 7 adults why stayed in this place. It was dated, but clean and lovely! Would stay again!!
    4 of 5 bubbles Reviewed 31 October 2016
    A lovely comfortable condo with plenty of space for two couples, equal standard rooms and bathrooms for each. A couple of minutes walk to an uncrowded extremely clean beach, and...
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    1 / 74
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
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    About this property
    We are pleased to offer our new 1 bedroom,1 bath upper level condo for rental. It has been redecorated throughout, is newly furnished and equipped to high standards, is very comfortable and located in well maintained lush Ekahi Village. The condo is close to the best of everything we enjoy, 3+... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 22 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 complex...
    5 of 5 bubbles Reviewed 25 October 2016
    This place is truly a paradise of sorts. Close to the beach and the condo itself is very clean, well kept and has everything you need to enjoy your stay. The Condo is stocked...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Wailea, Maui 96753
    1 / 23
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Aloha Maui vacation planners, Welcome to beautiful Wailea, a Master Planned Community which ensures good community planning and utilizes design guidelines to help preserve Maui's sophisticated island environment. Grand Champions Villas is located in the heart of Wailea and nestled between The... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 6 October 2016
    This was a wonderful vacation for myself, husband and daughter. We were delighted with our stay and all the tips left by Paul and Jessica. So close to beaches and excellent food...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    About this property
    Our condo in Ekolu Village also has beautiful sweeping views of the ocean and the islands. We are located on the Blue Golf Course and just a short walk to the shops and restaurants in Wailea. Just beyond the shops and restaurants is a beautiful walkway along the beach and hotels. Our condo is... View all property information
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    Wailea, Maui 96753
    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi Internet connection. Three flat screen TVs have been installed. Personal touches for your enjoyment and convenience. This unit is a 2,000-square-foot townhouse, occupying both the... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 29 March 2015
    We were very pleased with our stay. Condo fully stocked. Beautiful views. Convenient location. Comfortable and roomy. Would stay here again.
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    1 / 35
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
    • Wi-Fi
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    • DVD Player
    • Mountain Views
    • Ocean Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We recently remodeled our condo with all new upgraded tumbled travertine-style flooring, new window shades and new furniture. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3 of the cost and not have to purchase every meal in a resort hotel? You'll have a... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 12 December 2016
    The owner, Cara, was great to deal with by email, everything that was represented of the property was true. It was a lovely home away from home, very comfortable and great...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Grill
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    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 square foot villa with large... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 29 November 2016
    Well stocked kitchen, very nice bathrooms, ample sized bedrooms except the smaller one downstairs. Good location.
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    1 / 20
    5 of 5 bubbles (37) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    • Internet Access
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    • Waterfront
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    • Pet-friendly
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    • x
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    About this property
    Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade has been completed resulting in a home away from home with only highest quality finishes.... View all property information
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 27 February 2016
    Welcome basket with tasty local treats greeted us! Makena Surf is a super location on Maui - front row seats to see whales in February (bring binoculars), steps from the beach...
    5 of 5 bubbles Reviewed 25 February 2015
    I was told about this condo in Australia and could not believe what I was told...then I arrived there and it was beyond what I could have imagined! The condo is fitted out...
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    1 / 24
    5 of 5 bubbles (24) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Washer
    • Mountain Views
    • DVD Player
    • Wi-Fi
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    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 and 1/2 baths, 550 sq. ft. completely furnished cottage with full kitchen. This cottage has it all. Spectacular furnishings and ocean views! Completely remodeled 1 bedroom cottage in Maui Meadows... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 3 weeks ago
    We arrived at Maui Hale Olina (Maui House Of Joy) as Dennis and Cynthia, the wonderful hosts have named the cottage, on February 8th, 2017 and what a beautiful surprise that day...
    5 of 5 bubbles Reviewed 25 January 2017
    Such a beautiful cottage!! Pictures do not do it justice. Dennis was amazing and very helpful upon arrival, even brought us fresh fruit from his trees. Very clean well cared for...
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    1 / 23
    4.5 of 5 bubbles (13) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Waterfront
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    • Patio
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 4 weeks ago
    This the second time we have rented this unit in the last 2 years. We have been very satisfied with our experience. Well maintained and good prices. Easy walk or drive to beach...
    5 of 5 bubbles Reviewed 13 July 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
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    1 / 8
    4.5 of 5 bubbles (19) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Waterfront
    • Washer
    • Patio
    • Internet Access
    • Grill
    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Located on world famous Keawakapu Beach in Wailea, Ekahi Village is one of the most sought after locations. Our totally renovated condo offers complete privacy, but is only steps to the beach. Unwind after a day at the beach or pool by watching our 46" Sony Bravia flat screen with surround sound... View all property information
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 12 September 2016
    A wonderful, spacious one bedroom condo. No view of water, just lush greenery since its a ground floor unit. Very close to pool and beach access. Wailea shopping just a short...
    4 of 5 bubbles Reviewed 27 February 2013
    My husband and I stayed in this unit for 3 weeks another couple joined us for 2 weeks. The owner was easy to work with and provided all the needed information to make our stay...
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    1 / 24
    5 of 5 bubbles (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Housekeeping...
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Polo Beach Club sits on quiet Polo Beach. It is a unique building located within feet of the beach. Our home is a completely remodeled 2 bedroom 2 bath unit. We always provide daily maid service and upon arrival you will receive a complimentary fruit basket. When you first enter our home look... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 22 January 2017
    Entering this condo takes your breath away. The palm trees, waves, beach, and whales! Yes, whales were waving welcome to us. Perfectly appointed from art to kitchen accoutrements...
    5 of 5 bubbles Reviewed 10 December 2014
    My wife and I have stayed in many locations in Hawaii in general and Maui in particular, but, overall, none can compare to the Polo Beach Club and in particular THIS unit. While...
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    1 / 19
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • DVD Player
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Come enjoy condominium living at its finest at Wailea Ekahi #17D. Located in the heart of Wailea, Maui - is a One bedroom, Two bathroom deluxe condominium on the 2nd floor with panoramic ocean views. Enjoy fabulous ocean and outer island views from the living room, dining room, kitchen and main... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 25 October 2014
    Stayed at Wailea Ekahi 17D.Everything about this condo was PERFECT. It was well kept; pristine....the view was breathtaking. This whole community was WONDERFUL. Pool area and...
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    1 / 19
    4 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Spring 2017 Discounted Rates! Book Early Promo Code: SPRINGSAVER! Wailea Ekahi Village #4E Second floor condominium is adjacent to a landscaped ravine and has beautiful tropical garden views. This location provides a quiet location, away from any road noise and a couple minutes' walk to the main... View all property information
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    Wailea, Maui 96753
    1 / 29
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Ask us about our other Ekahi Village condos for rent Aloha ! Condo # 50-C - Luxury at an affordable price - perfect for a getaway or honeymoon. (4maximum) Low Season rate (Apr 16 - Dec 15) $175.00 per night High Season rate (Dec 16 - Apr 15) $275.00 per night This is a romantic 1bed/1bath,... View all property information
    Location Information
    Wailea, Maui 96753 9533
    3 of 5 bubbles Reviewed 2 February 2012
    This one-bedroom condo (with hide-a-bed couch in living room) was obviously recently updated - the kitchen, bathroom and bedroom all had nice, tasteful, simple furniture...
    5 of 5 bubbles Reviewed 5 May 2011
    I don't know about you, but if I wanted to stay in a resort with a million it other people and had a 3 mile treck to the beach or pool....I could stay anywhere! Valley Isle #302...
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    1 / 36
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles 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...
    5 of 5 bubbles 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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    1 / 12
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tastefully remodeled, this two bedroom, two bath condominium has many upgrades including a new contemporary kitchen with granite counter tops and stainless steel appliances. The master bathroom and guest bathroom were beautifully remodeled in 2015. Vaulted ceilings in the living room add to the... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 24 August 2016
    Loved the location and amenities. Very nice kitchen and master bathroom. We would stay there again. Hope the TV gets fixed. Disappointed we were unable to watch the Olympics...
    5 of 5 bubbles Reviewed 13 July 2016
    Beautiful place, great view, great location. Spacious condo with a great floor plan and within walking distance to the Wailea Mall. The beach is a short drive away. I would love...
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • x
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    • ?
    About this property
    Spring Saver Rates 2017 - Book Early! Promo Code: SPRINGSAVER! Enjoy views of Kahoolawe, Molokini and Lana’i all from this condo’s wonderful location. Vaulted ceilings, fresh paint, and brand new furnishings throughout entire condo. Comfortable living room furniture for conversing, watching a... View all property information
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    Wailea, Maui 96753
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    About this property
    Wailea Ekolu is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low density village consists of eighteen two-story buildings spread out over 18 acres of tropical landscaping and is conveniently located across from the... View all property information
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    Wailea, Maui 96753
    1 / 24
    5 of 5 bubbles (14) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Maui Rendezvous, Wailea Ekahi 33A, is a luxury (beautiful, romantic, and family friendly) 1,100 square-foot 1 bedroom 2 bath condo that sleeps 5. It is in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 13 September 2014
    We loved the condo and the owners are great. We also loved it as a base camp for exploring the island. Very convenient to other resorts and highways. They provide everything you...
    5 of 5 bubbles Reviewed 10 September 2013
    Our family of 3 stayed at Maui Rendezvous for 4 nights in August. We had a great time! The condo was clean and spacious. It was well equipped and everything was in good...
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Spring Saver Rates 2017!! This beautiful two bedroom, two bath condominium overlooks the Wailea Blue Course. Enjoy the golf and ocean views while sitting on the lanai for sunset or morning coffee. The living area features a large open floor plan, a 55” flat screen TV, and high speed wireless... View all property information
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    Wailea, Maui 96753
    1 / 31
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a recently renovated luxury first floor condo in Wailea's premier Grand Champions Villas. Our home is unit #103 on the east side of the complex. Spend your vacation enjoying this 1 bedroom, 2 bath unit that provides ample space to spread out,... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 23 April 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 bubbles Reviewed 10 September 2013
    I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
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    1 / 16
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • x
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    • x
    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... View all property information
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    Wailea, Maui 96753
    1 / 78
    4.5 of 5 bubbles (3) Very good
    Studio, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    <b>Golden Mandarin Pool Villa D102 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 Awards published on October 18, 2016.</b> The Wailea Beach... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 30 January 2015
    We have been coming to Wailea for the past 15 years and the Golden Mandarin was by far the best place we have ever stayed. The Villa was exquisite and was stocked with every...
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    1 / 23
    5 of 5 bubbles (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Patio
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
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    • x
    About this property
    Welcome to our home! Enjoy the fantastic ocean views and luxury of our home in Wailea Elua Village - a gated, 24 acre, oceanfront community. Our home is perfectly situated in the center of the Wailea Elua Village property (Unit #701). We are 150 yards from Ulua Beach -- just a 90 second walk to... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 8 December 2016
    Perfect Wailea condo for the four of us to stay! Had everything we needed plus more! Close to the pool, beach & shops! The deck was large & we definitely appreciated the barbecue...
    5 of 5 bubbles Reviewed 11 October 2015
    My sister and I stayed at this condo for five nights in September. The condo is in the perfect location within Elua Village. The beach and pool pavilion are only a few minutes...
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    1 / 14
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Balcony
    • Satellite TV
    • Hot Tub
    • Wi-Fi
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
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    About this property
    Spring Saver Rates 2017 Super Specials - Book Early !! All New Upgraded Kitchen and Baths. Grand Champions 54 offers a large 54" flat screen TV, DVD player, CD player, Ipod dock, high speed and wireless internet. The living room has air conditioning, ceiling fan and vaulted ceiling with a separate... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 23 November 2011
    We had stayed at Grand Champions last year so we were familiar with the complex and the location.....both reasons why we chose to come back here. This upstairs unit is pretty much...
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    1 / 26
    4.5 of 5 bubbles (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
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    • Grill
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles 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...
    4 of 5 bubbles 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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    1 / 16
    4.5 of 5 bubbles (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    A Note from the Owner: We chose Maui as the prefect location for our second home based on year around outstanding weather. Every day has highs in the 80s and generally bright sunshine. Our favorite hobby is golf. There are 5 courses within a few miles radius of Ekolu. Our favorites are the Wailea... View all property information
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    Wailea, Maui 96753
    1 / 20
    5 of 5 bubbles (41) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
    • Internet Access
    • Hot Tub
    • Grill
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
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    About this property
    Visit www.rainbowdeluxe.com for more info! Rainbow Deluxe is a standout 2 bedroom / 2 bath vacation home conveniently located in Maui Meadows, along the south shore of Maui, Hawaii. This 700 square foot luxury Polynesian pole cottage sits on its own quarter acre, private driveway entrance, ideally... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 3 weeks ago
    You won't need to look any further; stay here. The owner has gone through great lengths to ensure a perfect stay. Anything you can think you may need is provided. This includes...
    5 of 5 bubbles Reviewed 4 weeks ago
    Upon arriving at Rainbow Deluxe we were exhausted. We were so delighted to open the fridge and see essentials already for us! This condo is clean and centrally located. From the...
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    1 / 17
    5 of 5 bubbles (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool...
    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    Special Spring Saver Rates 2017 - Book Early ! Grand Champions #35 is an inviting third floor, two bedroom, two bath, Ocean View condo. The living room has sofa and love seat, A/C, Large Flat Screen TV, and Blu-Ray player. The newly updated kitchen has granite counters, new tile floor and full size... View all property information
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    Wailea, Maui 96753
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Balcony
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Spring Saver Rates 2017 - Book Early ! Grand Champions #102, located on the Second floor offers Fantastic views of the Wailea Blue Golf Course and the Haleakala mountainside. It is a short walk to either of the pools, Jacuzzi, barbeque areas. Wake up and enjoy the sunrise over Haleakala as you sip... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Makena Surf Resort is a luxurious secluded beachfront condominium located in the exclusive Wailea / Makena area. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting the... View all property information
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    Wailea, Maui HI
    1 / 24
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Patio
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Unbelievable 2 bedroom plus den / 2 bath penthouse villa located in the prestigous Wailea Beach Villas. Second floor location with 2000 interior square feet and 375 square foot covered lanai. Formal entry hall with artwork. Spacious living room with Tommy Bahama furniture. Dining room with table... View all property information
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    Wailea, Maui 96753
    1 / 14
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful ocean view unit is situated in upper Wailea Ekahi Village. It is a 952 square foot unit on the second floor with one bedroom and two full bathrooms. It comfortably sleeps 4 guests. Two in the bedroom and two on the memory foam sofa sleeper. It is conveniently located near one of the... View all property information
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    Wailea, Maui 96753
    1 / 23
    5 of 5 bubbles (20) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
    • Wi-Fi
    • Washer
    • DVD Player
    • Outdoor Dining Area
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Great Deal last minute rate for a luxury rental in Wailea. LAST MINUTE AVAILABILITY SPECIAL: APR 7-11, 4 NTS APR 18-MAY 02, 14 NTS $130/NT + $100 CLEANING FEE + 13.42% TAX THERE IS A SEPARATE US$200.00 REFUNDABLE... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 23 April 2016
    This unit was perfect for us because we did not have to bring anything else beside our basic clothes for our holidays. It has a full kitchen, washer-dryer, beach towels, beach...
    5 of 5 bubbles Reviewed 23 June 2014
    Condo was very clean and with chocolates upon arrival. Beautiful island décor and kitchen was well stocked with basics to prepare meals. Plenty of furniture to store your...
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    1 / 18
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
    • Grill
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Spring 2017 Deals Available! Book Early! Promo Code: SPRINGSAVER! Wailea Ekahi #41B is a lovely ground floor condominium furnished with a King bed in the master bedroom as well as air conditioning in both the living room and bedroom. There are ceiling fans throughout, Flat screen TV in living room... View all property information
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    Wailea, Maui 96753
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Brand New on Market INTRODUCTORY SPECIAL ONLY $399 Feb 25th - March 3rd ONLY $429 REMAINING MARCH OPENINGS Welcome to our Cloud 9 Beach House. Local Maui couple Tamara and Steve Farwig invite you to stay with us in our lovely new home just a short walk to the beach. Keawakapu, a beautiful long... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 6 February 2017
    We stayed here last week and had a wonderful week away. Its a newly renovated house and all of the bedrooms were a good size so suitable for a family or couples. The location was...
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    A Note from the Owner: We enjoy spending time out on the lanai, which has a large grassy area behind it that is great for our grandchildren to play ball on. Ulua beach is just a short walk and it's great for paddle boarding, boogie boarding and snorkeling. The Shops at Wailea are also just a short... View all property information
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    Wailea, Maui 96753
    1 / 12
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Reviews praise this "EXCEPTIONAL PRIME OCEANFRONT CONDO" that's just a few steps to its soft sand beach! "Sunsational" recently remodeled for island living at its best in one of Polo's few "prime luxury oceanfront" available as a rental in Maui's finest area. ADULT NON SMOKERS. 803 has the... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 12 August 2013
    My husband and 2 sons stayed in this beautiful condo last week. It is quite a place! Every attention to detail is incredible from the beginning correspondence from the owner until...
    5 of 5 bubbles Reviewed 7 July 2013
    Since our last review, we have stayed there twice. The owner has not only maintained the condo in pristine condition but has updated the master bedroom and bath. The owner is...
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    1 / 86
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
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    About this property
    <b>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’ Choice Awards published on October 18, 2016.</b> The Wailea Beach... View all property information
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    Wailea, Maui 96753
    1 / 19
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • DVD Player
    • Hot Tub
    • Wi-Fi
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    • Satellite TV
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Spring Saver Rates 2017! Book Early ! Grand Champions 163 is a delightful ground floor two bedroom tiled throughout with the exception of the bedrooms. Beautiful, Kitchen and Vanity Cabinets with Granite Counter tops. The Living room has a cozy sectional sofa, flat screen TV, DVD, wireless... View all property information
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    Wailea, Maui 96753
    1 / 22
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Spring Saver Rates 2017! Grand Champions 8 is a top floor tropical delight with lush foliage surrounding the lanai for privacy. There is a spacious airy feeling with vaulted ceilings and ceiling fans in the living area. It is comfortably furnished, has A/C if needed, large flat screen TV, DVD... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed 1 week ago
    This was a large and spacious condo. It didn't have the sweeping water view that we expected,(from one bedroom only). The air conditioning was so loud in each bedroom it was...
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    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Housekeeping...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautifully furnished and well appointed, with gorgeous views and 3 large Lanais. This is a very comfortable "home away from home" with many special amenities, full kitchen and BBQ. Newly remodeled and next to the Quiet Upper Pool, it is private, quiet and very spacious 1550 sq ft. Surrounded by... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles 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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    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Spring Saver Rates 2017 - Book Early! Use Promo Code: SPRINGSAVER!! Wailea Ekolu 1606 is a top floor two bedroom two bath condo with a wonderful ocean view. Beautiful wood flooring throughout, vaulted ceilings, spectacular kitchen and classy island decor. The living area is Air Conditioned, has a... View all property information
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    Wailea, Maui 96753
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
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    • x
    About this property
    Wailea Ekolu Village is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low density village consists of eighteen two-story buildings spread out over 18 acres of tropical landscaping and is conveniently located across... View all property information
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    Wailea, Maui 96753
    1 / 76
    5 of 5 bubbles (9) Excellent
    Studio, 4 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    <b>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 Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 1 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...
    5 of 5 bubbles Reviewed 30 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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    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.