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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 / 22
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 square foot villa with large... View all property information
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    Wailea, Maui 96753
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • DVD Player
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    • Ocean Views
    • Mountain Views
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    About this property
    Ocean View, Spacious, Paradise! ~^~^~^~^~^~^~^~^~^~^~^~^~^ Luxurious LARGE two bedroom, two full bath condo in a private, secure beachfront village. This unit has a partial ocean view from the glass-paneled lanai, as well as from the master bedroom and living room, and is just five minutes' stroll... View all property information
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    Wailea, Maui 96753
    1 / 74
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    We are pleased to offer our new 1 bedroom,1 bath upper level condo for rental. It has been redecorated throughout, is newly furnished and equipped to high standards, is very comfortable and located in well maintained lush Ekahi Village. The condo is close to the best of everything we enjoy, 3+... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 15 September 2014
    I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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    1 / 35
    5 of 5 stars (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
    • Shared Outdoor Pool...
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    About this property
    Experience the REAL 'Old Hawaii' in our private unattached HOUSE, NOT a noisy condo, ohana or part of a house. LEASE JUNE 1 - NOV 30 at $3,999/mo. You will feel the ocean breeze, see it and clearly HEAR the ocean on this culdesac. From deck to ocean is about 200 yards in which you can walk to the... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 5 April 2016
    My wife and I spent 10 days here and had a blast. It's located very close to the beach where you can hear the waves. The landscapping is beautiful and is grown up to keep you...
    5 of 5 stars Reviewed 15 May 2014
    For me as an artist, staying at Sam and Rebecca's cottage, inspired a number of drawings, photographs and watercolors. My husband was able to disconnect from electronic media and...
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    1 / 7
    4 of 5 stars (5) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Grill
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Location: Ekahi Village, Wailea, South Maui, Maui, Hawaii, USA (Maiu Airport & Town of Kahalui 12 mi. Kihei Town 6 mi.) Accommodations: Condo, 1 Bedroom + Convertible bed(s), 2 Baths (Sleeps 2-4) Keywords: Condominium This Wialea Ekahi unit is a one bedroom, two bath unit (with a queen... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 23 December 2014
    This is a wonderful condo - nicely decorated, well stocked kitchen, and comfortable. They also had a good supply of beach gear. The 2nd bathroom is a real benefit. It is a short...
    5 of 5 stars Reviewed 4 November 2014
    We would like any potential renter to read this review and say to themselves, "Ah, finally I've found the place I've been looking for!" We know what it's like to pick a place...
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    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • DVD Player
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    • Air Conditioning
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    • Satellite TV
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    • Pet-friendly
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    About this property
    Features of our four bedroom three bath villa include: Over 3000 sq ft of living space, sleep up to 8 guests Two separate master suites with large walk in closets Two bedrooms can have either two twins or king bed Dramatic Great Room with oversized sofa with surround sound system Waterworks... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Outdoor Dining Area
    • Balcony
    • Satellite TV
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    About this property
    Ekolu #1108. Two-bedroom, two bath Ekolu condo with breathtaking ocean view! 180 degrees spanning from West Maui, to Lanai, across Maalaea Bay, above the Wailea Resorts, past Molokini, and even beyond the island of Kahoolawe. Some condos provide fantastic sunsets part of the year, this one... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 11 November 2011
    We booked this condo for 8 days. It was everything that had been described to us and more. The view was fantastic. Everything we needed was there, all we had to bring was our food...
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    1 / 22
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Mountain Views
    • Wi-Fi
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    • x
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    About this property
    This ground floor corner villa at Grand Champions Resort features three bedrooms, two baths, a fully equipped gourmet kitchen, and two lanais. Surrounded by the manicured fairways of Wailea's famed Blue Golf Course and the spectacular grounds of the Wailea Tennis Club, this quiet, well-managed... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 20 April 2015
    The condo was spacious, clean and homely. They had everything we needed and the complex was well maintained. very close to Wailea town centre and 15 min walk to resort area. BBQ...
    4 of 5 stars Reviewed 21 December 2013
    We were a group of 6 adults and one toddler and we felt totally at home here and would definitely recommend this condo our friends. Set in an amazing area with world class...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Beautifully Remodeled and furnished two bedroom Condo overlooking the Golf Course. The kitchen ad bathrooms have been recently renovated. This unit offers many upgrades throughout and has many new furnishings. The bedrooms have all new furniture and the master bedroom features a beautiful wooden... View all property information
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    Wailea, Maui 96753
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Two bedrooms and two baths in this garden view condo. The Master bedroom has a king bed and the second bedroom has a queen bed, allowing this unit to sleep up to four people. This ground floor unit is tiled in all of the common areas and carpeted in the bedrooms. The living area is a great place... View all property information
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    Wailea, Maui 96753
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Waterfront
    • Grill
    • Patio
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    • Ocean Views
    • Balcony
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    Wailea Elua Village is a true oceanfront resort. Upon entering our condo there is an unobstructed panoramic view of the ocean, lanai, living room, dining room and kitchen. From the condo guests can stroll the Wailea Coastal Beach-Walk Path to breakfast, lunch, dinner or cocktails at some of the... View all property information
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    Wailea, Maui 96753
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Hot Tub
    • Sauna
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Ocean Views
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Located across the street from the world renowned Wailea Beach, Ho'olei 81-1 is unequaled in splendor, elegance and convenience. Let this exceptional three bedroom, three and a half bath, two-level residence be your home away from home for your dream Hawaiian vacation. Every aspect of this... View all property information
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    Wailea, Maui 96753
    1 / 19
    5 of 5 stars (7) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • Grill
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named with vaulted ceiling, HD TV, DVD, wireless internet and formal dining area. Tropical blue and turquoise colors convey a serene ambiance comparable to the pristine... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 24 July 2014
    Our vacation rental was clean, spacious, quiet and most importantly, had great views. If you are looking for a great family rental on your vacation, I highly recommend Ho'Olei!
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    1 / 25
    5 of 5 stars (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Washer
    • Mountain Views
    • DVD Player
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    • Waterfront
    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 and 1/2 baths, 500 sq. ft. completely furnished cottage with full kitchenThis cottage has it all. Spectacular furnishings and ocean views!Completely remodeled 1 bedroom cottage in Maui Meadows (Maui... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 4 days ago
    My other half and I decided to try this beautiful cottage for two weeks, once we found what we thought would fit our needs & wants, we booked it. Wow did we ever come across a...
    5 of 5 stars Reviewed 1 March 2016
    These photos don't do the cottage justice ! It's really special and highly recommended cottage for 2 to re-charge your batteries in. We spent 8 nights here unwinding, relaxing up...
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Spend your vacation at Ho'olei luxury villas at Grand Wailea on Maui! Located just minutes from the world-class Grand Wailea Resort Hotel & Spa on Maui's southern shore, each two-story villa offers a luxurious home in paradise. Every villa has three bedrooms and 3.5 baths with finely appointed... View all property information
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    Wailea, Maui 96753
    1 / 16
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Waterfront
    • Shared Outdoor Pool...
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    Spring 2016 Specials - please inquire! Wailea Ekahi 3C is a charming one bedroom, one bath, first floor garden view condo. It is a great choice for singles or couples wanting a reasonably priced condo close to the beach. The private garden setting is great for relaxing and enjoying the soft sands... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 4 November 2011
    We love staying at Ekahi Village condos. We have stayed here multiple times, this last time in 3C. What we love most is that there are no surprises, everything is exactly as...
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    1 / 24
    5 of 5 stars (16) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Hot Tub
    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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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... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 12 December 2015
    1st off I have to say... I can't wait to go back to this space!!! My partner and I stayed In Lawrence's beautiful condo! Tasteful and stylish with its decor, with its...
    5 of 5 stars Reviewed 9 June 2015
    Beautiful condo. Nicely furnished. Well-equipped kitchen. Great Lanai with BBQ. Supplied snorkel gear, beach chairs and umbrella. Owner, Lawrence, a pleasure to deal with.
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    1 / 31
    5 of 5 stars (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • Mountain Views
    • Wi-Fi
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
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    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
    Location Information
    Wailea, Maui 96753
    4 of 5 stars Reviewed 23 April 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 stars Reviewed 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 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Children's Pool
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    • Pet-friendly
    • Wheelchair access
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    • x
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    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
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    Wailea, Maui 96753
    1 / 28
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • Elder access
    • x
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    About this property
    Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. This spacious 1148 square foot condo has a great layout for privacy. The large bedrooms are on opposite sides of the condo with their own private... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 1 October 2015
    Isn't it amazing when you step into a place and it's JUST like the pictures? Or even better? From the second we walked in we knew this was the place to be. Beautifully appointed...
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    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
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    About this property
    Trip Advisor Guests Describe L409 as 'Perfect & Well Worth the Money'. Visit our website for additional pictures to see why this villa is the most popular unit there based on travelers reviews. Luxurious 3000' Panoramic Oceanview Villa Available at Owner Direct Low Prices. This breath taking... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 stars (6) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Satellite TV
    • Balcony
    • DVD Player
    • Washer
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    • Air Conditioning
    • Waterfront
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
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    About this property
    Aloha! 29F is located in the lower village and has arguably the best view in Ekahi Village. This professionally remodeled unit comes with all the amenities of a five star hotel, yet all the comforts of home. Ocean front gourmet kitchen, lanai and living room. Pool and beach are just steps away.... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 10 October 2013
    My husband and I stayed at Unit 29F Oct. 1 - Oct. 6, 2013. It was our first trip to Maui and our first experience renting a condo vs. staying at a resort. We definitely made the...
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    1 / 45
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Mountain Views
    • Sauna
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    • DVD Player
    • Children's Pool
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Modern Maui, our ocean view villa located in the heart of beautiful Wailea, combines all the best elements of a premium vacation home: Location, space, amenities and Grand Wailea Resort access. EXCLUSIVE GRAND WAILEA RESORT BENEFITS FOR OUR GUESTS: * On-demand, free transportation to and from... View all property information
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    Wailea, Maui 96753
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Look no further! This is the condo for you! The Wailea Grand Champions is one of the premier vacation rental properties on the south side of Maui in the town of Wailea. A few minutes from the property are high-end five star resorts like the Four Seasons and the Grand Wailea. Also within minutes... View all property information
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    Wailea, Maui 96753
    1 / 27
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Balcony
    • DVD Player
    • Hot Tub
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    • Parking
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. Our condo has a terrific layout with the bedrooms being on opposite sides of the condo. Each has its own private washroom, flat screen TV and... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 18 September 2013
    Once again, I loved everything about this condo. Beautiful first class furnishings, close to wonderful beaches in Wailea & Makena, & great shopping. The extra touches like the...
    5 of 5 stars Reviewed 20 November 2012
    The condo was beautifully furnished. We appreciated all the extras that made this stay so relaxing like the Tommy Bahama beach chairs, boogie boards, beach towels, & beach...
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    1 / 26
    5 of 5 stars (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    FREE TELEPHONE TO THE MAINLAND AND CANADA. JUNE AVAILABILITY: Arrive June 1st, depart June 5th OR arrive June 8th, depart June 11th. $125/night plus tax (13.416%) and cleaning $75. LATE JUNE AND 4TH OF JULY: Arrive June 25th, depart July 1st OR arrive July 3rd, depart July 12th $125/night... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 28 January 2016
    We absolutely loved your unit. This our second time staying at Grand Champions. Everything was absolutely perfect. Nice big unit with tons of amenities. Use of the pool and...
    5 of 5 stars Reviewed 25 January 2014
    My partner and I came to Maui to run the Maui Oceanfront Marathon. We had booked a room at the Marriott for which the marathon had a room block. However, because we wanted to...
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    1 / 35
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
    • Wi-Fi
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    • DVD Player
    • Mountain Views
    • Ocean Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    We recently remodeled our condo with all new upgraded tumbled travertine-style flooring, new window shades and new furniture. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3 of the cost and not have to purchase every meal in a resort hotel? You'll have a... View all property information
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    Wailea, Maui 96753
    1 / 26
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 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...
    5 of 5 stars Reviewed 3 May 2015
    I loved this studio. It was very nice space with a deck. It has a stackable washer/dryer. The bed was super comfortable and owners were responsive to my needs. At the time I was...
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    1 / 23
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
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    • Hot Tub
    • Patio
    • Shared Outdoor Pool...
    • Washer
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
    About this property
    Welcome to our home! Enjoy the fantastic ocean views and luxury of our home in Wailea Elua Village - a gated, 24 acre, oceanfront community. Our home is perfectly situated in the center of the Wailea Elua Village property (Unit #701). We are 150 yards from Ulua Beach -- just a 90 second walk to... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 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...
    5 of 5 stars Reviewed 6 August 2014
    We stayed for five days in July with 2 children and 2 adults. The unit was exactly as advertised and had everything and more that we needed during our stay. The view from lanai...
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    1 / 20
    5 of 5 stars (23) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Balcony
    • Mountain Views
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Our second story 3 bedroom villa with 1383 feet, is located in the beautiful Grand Champion Complex, located in the resort area of Wailea. Our corner villa offers a panoramic view of the West Maui Mountains as well as the ocean. The villa also overlooks the seventh farway of the Wailea Blue... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 15 June 2014
    This is one of the best condos we have ever had the pleasure to stay in while visiting Maui. I read numerous reviews which had stated how well stocked the condo was. I would...
    5 of 5 stars Reviewed 14 October 2011
    Just ended our 9-day vacation on Maui. The condo was perfect for our group of 4 adults and two girls under 10. Everyone thought the condo was very nicely decorated, nice...
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    1 / 19
    5 of 5 stars (43) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Satellite TV
    • Grill
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wow ! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui Wailea, Ekahi Village condo (28D). Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than four minutes.When you... View all property information
    Location Information
    Wailea, Maui 96753 9532
    5 of 5 stars Reviewed 1 week ago
    We just got back from staying in 28D and we found ourselves several times saying the condo was better than the website. The owners have done a great job outfitting the condo and...
    5 of 5 stars Reviewed 23 March 2016
    My stay at the Peabody's Condo was a visit to Paradise. The view from every room was stunning. The unit has been recently remodeled and you think you are walking into a brand...
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    1 / 21
    5 of 5 stars (14) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Housekeeping...
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • 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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars 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 stars Reviewed 10 September 2013
    Our family of 3 stayed at Maui Rendezvous for 4 nights in August. We had a great time! The condo was clean and spacious. It was well equipped and everything was in good...
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    1 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
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    • Grill
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • DVD Player
    • Washer
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 13 July 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
    5 of 5 stars Reviewed 2 March 2015
    This is a spacious condo with all the amenities you'd want for your vacation -- including a washer and dryer inside the condo and a full patio with BBQ. The setting is beautiful...
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    1 / 29
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Outdoor...
    • Washer
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Note: *** Our calendar is always up to date. Low Season Rate (Apr 16 - Dec 15) $395.00 per night High Season Rate (Dec 16 - Apr 15) $450.00 per night Are you looking for a quiet peaceful alternative vacation experience away from the hotel zone but minutes away from South Maui's best beaches,... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 27 July 2014
    We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
    5 of 5 stars Reviewed 8 July 2014
    The wife and I and are 3 children (9, 9 and 3) stayed here for 8 nights! Looked at many homes in Maui and man did I nail it with this one! Perfect location, perfect owners...
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    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Ocean Views
    • Grill
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Grand Champions Villas in Wailea are one of the fan favorite condominium properties in Wailea. Located minutes from five star resorts like the Four Seasons and Grand Wailea, this property is right where you want to be when vacationing on Maui. The Shops at Wailea, complete with high-end... View all property information
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    Wailea, Maui 96753
    1 / 24
    4 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Hot Tub
    • Internet Access
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    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious living room opens to the Lanai, where there is ample space for stretching out and relaxing in the sun, barbecuing on your own private grill, or admiring the tropical grounds of The Palms at Wailea.... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 15 February 2015
    This is a terrific location for a visit to South Maui. We used the whale watch rafts from the Kehei ramp. Close to Safeway, beaches with full service and beach parking. Loved...
    4 of 5 stars Reviewed 2 August 2014
    We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
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    1 / 37
    5 of 5 stars (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Housekeeping...
    • Mountain Views
    • Children's Pool
    • Sauna
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    GRAND WAILEA RENTAL PROGRAM BENEFITS FOR OUR GUESTS: * Complimentary on-demand transportation to and from The Grand Wailea Resort * Enjoy the use of all the pools, water slides, spa and restaurants at The Grand Wailea Resort * Exclusive charging privileges at The Grand Wailea Resort *... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 26 November 2015
    Aloha! We have stayed at Hoku Ho'Olei for the past 4 years and I have already booked my trip for July, 2016! Love this villa and the owners. Very beautiful, comfortable and all...
    5 of 5 stars Reviewed 11 August 2014
    I must say that this was one of the best vacation rentals I've stayed at. The house, staff and property was simply amazing. Everyone there was extremely courteous, friendly and...
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    1 / 14
    5 of 5 stars (21) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Parking
    • Wi-Fi
    • Washer
    • DVD Player
    • Patio
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    NEXT AVAILABLE SHORT OPENINGS AS LISTED BELOW: SPECIAL, UNIQUE STUDIO IN THE HEART OF WAILEA. YOU MIGHT PAY LESS, BUT YOU CAN'T GET MORE FOR YOUR MONEY! MAY 30-JUN 04; JUN 10-12; JUN 15-17; JUN 27-JUL 02 ARE OUR NEXT SHORT OPENINGS IN THE STUDIO. SEE CALENDAR... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 1 October 2013
    Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
    5 of 5 stars Reviewed 29 September 2012
    We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Relax on your lanai, enjoying the radiant blue waters to your west, and the stunning sights of Haleakala to your east. Overlooking the pristine fairway, beyond which the ocean shimmers, you'll find your stay in Grand Champions 75 to be a welcome tropical retreat from all of your worries and cares.... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 stars (29) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Ekahi 1BD/2BA 20B is a beautiful, spacious condo in the LOWER VILLAGE of Ekahi, at the bottom of the hill and closest to the beach. In fact it's only a 2 minute walk to world renowned Keawakapu Beach! And because the walk path is nearly level, you avoid hiking up the hill with all your beach gear... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 16 March 2016
    This rental is fantastic, my wife and my 2 year old went in February. Not only was the rental a great space, with nice appliances (and the sharpest chef knife I've ever had in a...
    5 of 5 stars Reviewed 12 February 2016
    We absolutely loved our stay at Ekahi 20B. We can't ain't to go back. The unit was spotless, well equipped and wonderfully located.
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    1 / 42
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Children's Pool
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Look no further!!!! Luxurious and exclusive 2 bedroom + den, penthouse unit, now offered at an AMAZING RATE!!!!!! Over 1900 sq. Ft + lanai! Panoramic ocean views, spectacular Hawaiian sunsets!!! Wailea Beach Villas VOTED #1 RESORT IN HAWAII BY CONDE NAST TRAVELER NOVEMBER 2014!!!!... View all property information
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    Wailea, Maui 96753
    1 / 20
    5 of 5 stars (37) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • 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
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    Wailea, Maui 96753
    4 of 5 stars 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 stars 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 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Patio
    • Satellite TV
    • Hot Tub
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Features of our 2500 sq oceanview condo include: Two full master suites Second bedroom can have two twins or king sized bed A den that closes off completely to sleep up two additional guests (either twin or king sized bed) Private Elevator Waterworks Bathrooms with large soaking tub Studio... View all property information
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    Wailea, Maui 96573
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
    About this property
    MAY SPECIAL May 15-21st only $450/night plus tax May 28th - June 4th only $450/night plus tax Come stay with us here in sunny south Maui at our beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around... View all property information
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    Wailea, Maui 96753
    1 / 24
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Housekeeping...
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    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 stars 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...
    5 of 5 stars Reviewed 28 November 2014
    We had seen positive reviews for #408 Polo Beach Club and really loved the pictures of the unit, so we had high expectations when we arrived at the unit. I'll have to say that...
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    1 / 41
    5 of 5 stars (23) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Mountain Views
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled in a quiet lower village setting right on the green belt, our Maui home has recently undergone a complete professional remodel. The ceiling has a real Hawaiian feel with beams and matting, we've opened the kitchen to the living room and created two master suites with private bathrooms. The... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 5 days ago
    We have stayed at Ekahi more than a dozen times and 11F is by far the most thoughtfully designed, equipped, and well-maintained condo we have rented. The rental process was easy...
    5 of 5 stars Reviewed 1 week ago
    The first impression upon entering this condo was the cleanliness. Everything was sparkling in the Maui sunshine. At the midpoint of our stay we understood why. We were treated to...
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    1 / 77
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Patio
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    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • ?
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    About this property
    Azure Azul M212 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! The Wailea Beach Villas is ranked <b>No. 7 in the Top 25 Best Resorts in Hawaii</b> by Conde Nast Traveler's Readers' Choice Awards, published on October 20, 2015. In May... View all property information
    Location Information
    Wailea, Maui 96753
    Wailea Holiday Rentals

    If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.

    Things to do in Wailea

    Obviously you will be wanting to hit the beach in Hawaii, and there are many from which you can choose, such as Keawakapu Beach, surrounded by golf courses. If you don't want to spend all your time lying on one of the many south-facing beaches but aren't quite brave enough to go and climb a volcano, Wailea has many things to do for all ages, from playing golf and tennis to the inevitable shops and restaurants, all in an incredible Pacific climate. Wailea is fairly sparsely populated, with around 6,000 inhabitants, so you can also have a great time exploring the countryside nearby.

    Renting villas and condos in Wailea

    Wailea Resort is a wonderful place to visit and stay, but its planning is a bit contrived - the Wailea Community Association issue guidelines for new buildings aiming to preserve the island feel of Maui. With the additional aim of low population density, this does mean that prices even for holiday rentals may be higher than in other parts of the Hawaii island chain. But with the scary prices charged by hotels, and the extra flexibility associated with renting your own villa or condo for your family, Wailea holiday rentals still represent fantastic value for money. With air conditioning thankfully coming as virtually standard, and difficult choices of whether you'd prefer views of a volcano, a golf course, or perhaps a beach, it's an idyllic place to enjoy a great family holiday. And if you are looking for a low cost Pacific break, nothing beats buying local produce and cooking it up in your very own kitchen for the week, rather than relying on a hotel's expensive restaurants.