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Holiday Rentals in Wailea, HI

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    ₹ 28,638 Average
    ₹ 67,000+
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    Travellers to Wailea are booking December dates now. Secure your holiday home today, and have the perfect trip.
    1 / 23
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 24
    5 of 5 stars (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    1 / 17
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • DVD Player
    • Children's Pool
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Live luxuriously while on vacation! Beautiful Hawaiian art, travertine floors, granite countertops, tall bath vanities, and elegant new furniture make this condo a place of comfort and serenity. The two bedrooms are private, each with an en suite bathroom. The master bedroom offers a California... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 2 November 2015
    Stayed in this really nice 2 bedroom/2 bath (upstairs) condo that was in a great location in Wailea, Maui. It is located near the Shops of Wailea, beaches, and restaurants (such...
    5 of 5 stars Reviewed 20 March 2015
    We spent a week in Maui for our son's first birthday. This condo was perfect for us, our little one, and my parents. The condo was clean and comfortable, beautifully furnished...
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    1 / 41
    5 of 5 stars (25) 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
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • 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 4 weeks ago
    Probably one of the nicest vacation rentals we have experienced. Every amenity is provided from the kitchen appliances to the comfy beds and linens. A spectacular ocean view...
    5 of 5 stars Reviewed 4 weeks ago
    Our family was so impressed with our rental of Ekahi 11. It was just as it's pictured in the listing. Beautiful, clean and inviting. The owner Peggy was helpful, attentive and...
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    1 / 74
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    • Waterfront
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 16 September 2014
    I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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    1 / 17
    5 of 5 stars (4) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Total renovation with high end finishes. All amenities: AC, HDTVs, free phone calls to US & Canada, free WIFI, Stainless Steel appliances, granite counters. Located in the upper part of Ekahi Village, an Ocean-Front community located on Keawakapu Beach, Wailea, South Maui. Non-Smoking ground floor... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 14 November 2014
    This condo was clean, well-equipped, and a five minute walk from the beach. The grounds were magnificent and even had an orchid garden. There was great snorkeling right off the...
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    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
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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. <BR><BR>Ocean front gourmet kitchen, lanai and living room. Pool and beach are just steps... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 11 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 / 12
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Mountain Views
    • Washer
    • Shared Outdoor Pool...
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 1 week ago
    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 stars Reviewed 14 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 / 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
    • 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
    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 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Shared Outdoor Pool...
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    This large 2 bedroom 2 bathroom villa has stunning views of the Old Blue Golf Course. Our spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. <BR><BR>Our condo has has a great layout for two couples. Each couple has there own... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 26 October 2015
    This is the second time I stay in this complex of apartments and I love it so much. It has everything; washing machine, dryer, dish washer, coffee maker and even boogie boards for...
    5 of 5 stars Reviewed 16 December 2013
    My wife and I stayed in unit 29 at the Grande Champions Golf Villas for two weeks in December, 2013. The property manager Kathleen was fantastic to deal with and responded...
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    1 / 27
    5 of 5 stars (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • 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!! Experience island life in our luxury, spacious, one bedroom. This rental is offered to you directly from a local couple intent on providing you with the ultimate vacation rental... View all property information
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    Wailea, Maui 96753
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Grill
    • DVD Player
    • Sauna
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 23
    5 of 5 stars (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
    • ?
    • Smoking allowed
    • x
    About this property
    Great Deal for a luxury rental in Wailea. AIRFARES ARE GOING DOWN IN AUGUST....TAKE THE OPPORTUNITY TO ENJOY THE LUXURY AREA OF WAILEA FOR A GREAT RATE...... LAST MINUTE AVAILABILITY AUG 27-31 $119/NT + $100 CLEANING FEE + TAX ".....Since we could only rent your... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars 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 stars 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 / 20
    5 of 5 stars (24) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Balcony
    • Mountain Views
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our second story 3 bedroom villa with 1383 feet, is located in the beautiful Grand Champion Complex, located in the resort area of Wailea. Our corner villa offers a panoramic view of the West Maui Mountains as well as the ocean. The villa also overlooks the seventh farway of the Wailea Blue... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 30 June 2016
    We had a fabulous time! Tony and Bev have taken well care of the home. Great advice on places to go and places to eat if you don't want to cook. Short walking distance to beach...
    5 of 5 stars Reviewed 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...
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    1 / 24
    5 of 5 stars (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Here's is your chance to experience this gorgeous condo at the Palms at Wailea. Newly renovated fully air conditioned, Charcoal grey bamboo floors, Whotel Pillow top Cal king mattress including the WHotel feather bed that makes you feel like your floating. There is also 2 flat screen TV's and the... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 26 May 2016
    We loved our stay at Lawrence's condo. The condo is beautifully remodeled and well-equipped. It is located perfectly between the beaches of Wailea and the cute town of Kihei...
    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...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
    • Air Conditioning
    • Parking
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    This 2 bedroom 2 bath condo offers so much gracious space with its large bedrooms, the beach home offer exceptional ocean and sunset views along with breathtaking sunrise views Imagine yourself in it on the world famous sandy beache. This partial ocean view condo is the best valued vacation spot... View all property information
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    Wailea, Maui 96753
    1 / 18
    5 of 5 stars (34) Excellent
    1 Bedroom, 3 Bathrooms, Sleeps 3 | Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Shared Outdoor Pool...
    • Washer
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    EXCELLENT LOCATION, BEAUTIFUL & PRIVATE OCEAN VIEW! Watch the surf, check out the beach and listen to the rhythm of the waves breaking onto black lava rock. Completely remodeled, refurnished & professionally decorated. Enjoy wonderful ocean, tropical gardens and Haleakala views. A true "Paradise... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 20 February 2016
    Every year we ask ourselves why staying in Ekahi 7G has become our favorite vacation spot? Could it be the beautiful decor we see every time we enter? Or perhaps it's because the...
    5 of 5 stars Reviewed 26 July 2014
    Just returned from Maui and Wailea Ekahi 7G delivers everything promised. The unit is beautifully decorated and has every imaginable amenity. The kitchen is extremely well...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    • Spacious living room and bedroom with ocean view and vaulted ceiling • Brand new BeautyRest air-cool pillow-top king size mattress • Very quiet split ACs in living room and bedroom with separate controllers. • TV/DVD/Cable in living room and bedroom, queen-size sofa sleeper • Free Wi-Fi access,... View all property information
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    Wailea, Maui 96753
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Housekeeping...
    • Patio
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful two bedroom (with queen beds), two bath condo is in a 150-unit complex, unit #704. Our second (top) floor location allows for privacy and the ability to leave the doors wide open to welcome the tropical breezes. A short walk to fabulous Wailea beaches and an even shorter walk to the... View all property information
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    Wailea, Maui 96753
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    1 / 24
    5 of 5 stars (11) 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
    Suitability
    • 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 stars Reviewed 11 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 / 19
    5 of 5 stars (21) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    • Internet Access
    • Patio
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    DIRECT PANORAMIC OCEAN VIEWS. IF OTHERS DON'T SHOW IT, CHANCES ARE THEY DON'T HAVE IT. THE PHOTO ABOVE TAKEN FROM THE DINING ROOM WINDOW.<BR>Stunning Ocean Views from recently renovated, lower village condominium. Two Master Suites, one with a King bed, the other with a King and twin brd, also a... View all property information
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 17 May 2016
    We love Maui and have been fortunate to stay in many beautiful condos there over the years. Ekahi 2A definitely falls into that category. Ocean views from this unit are to die...
    5 of 5 stars Reviewed 29 December 2015
    Ekahi Village 2A is an absolute dream. Bright and modern, clean and spacious, the owners have shown excellent taste in refurbishing this condo. There is nothing to improve on...
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    1 / 19
    5 of 5 stars (43) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wow ! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui Wailea, Ekahi Village condo (28D). Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than four minutes.When you... View all property information
    Location Information
    Wailea, Maui 96753 9532
    5 of 5 stars Reviewed 15 May 2016
    We just got back from staying in 28D and we found ourselves several times saying the condo was better than the website. The owners have done a great job outfitting the condo and...
    5 of 5 stars Reviewed 24 March 2016
    My stay at the Peabody's Condo was a visit to Paradise. The view from every room was stunning. The unit has been recently remodeled and you think you are walking into a brand...
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    1 / 20
    5 of 5 stars (38) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed 23 May 2015
    My wife and I spent the first week of our honeymoon in Rainbow Deluxe and could not have been happier! It was perfect! When we arrived there was a cornucopia of fruit, snacks and...
    5 of 5 stars Reviewed 23 March 2015
    We wanted to experience a part of our trip as the locals live and this house was perfect for our needs. Well appointed and comfortable! The beautiful garden with romantic view...
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    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Housekeeping...
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • 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
    Location Information
    Wailea, Maui 96753
    5 of 5 stars 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 / 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
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade has been completed resulting in a home away from home with only highest quality finishes.... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 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 26 February 2015
    I was told about this condo in Australia and could not believe what I was told...then I arrived there and it was beyond what I could have imagined! The condo is fitted out...
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    1 / 20
    5 of 5 stars (12) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Ocean Views
    • Washer
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Grand Champions #162 is a spacious, one-bedroom, two-bath, ocean view condo. Great 2nd floor, end-unit location for quiet and privacy. Vacation in sunny South Maui in a beautifully furnished, ocean-view condominium at Grand Champions Villas in exclusive Wailea, Maui's premier vacation destination.... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 25 March 2016
    #162 at Grand Champions was just as advertised. Nice view of the golf course with the ocean in the distance. Reasonably good view of the sunsets. The unit was very clean with...
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    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Satellite TV
    • Balcony
    • Hot Tub
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    About this property
    Please ask us about our Spring 2016 Specials. Grand Champions 186 is located on the second floor and overlooks one of the 2 pools on property. Featuring a modern Hawaiian theme throughout. The living room has a large High Definition TV with DVD, high speed and wireless internet, comfy sectional... View all property information
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    Wailea, Maui 96753
    1 / 23
    4.5 of 5 stars (11) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 13 July 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
    5 of 5 stars Reviewed 3 March 2015
    This is a spacious condo with all the amenities you'd want for your vacation -- including a washer and dryer inside the condo and a full patio with BBQ. The setting is beautiful...
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    1 / 12
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Balcony
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Reviews praise this "EXCEPTIONAL OCEANFRONT CONDO" that's just a few steps to its soft sand beach! "Sunsational" newly remodeled condo offers island living at its best in Maui's finest area. The penthouse is only available to ADULT NON SMOKERS... Enjoy Wailea-Makena and the resort's best... View all property information
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    Wailea, Maui 96753
    5 of 5 stars 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 stars 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 / 16
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second floor. Sitting on the lanai at sunset, we feel the... View all property information
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    Wailea, Maui 96753
    1 / 30
    5 of 5 stars (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 / 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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    • Pet-friendly
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    • x
    • x
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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 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 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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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 stars 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 stars (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Mountain Views
    • Patio
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    • Porch
    • Grill
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Experience the REAL 'Old Hawaii' in our private unattached HOUSE, NOT a noisy condo, ohana or part of a house. LEASE JUNE 1 - NOV 30 at $3,999/mo. You will feel the ocean breeze, see it and clearly HEAR the ocean on this culdesac. From deck to ocean is about 200 yards in which you can walk to the... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 5 April 2016
    My wife and I spent 10 days here and had a blast. It's located very close to the beach where you can hear the waves. The landscapping is beautiful and is grown up to keep you...
    5 of 5 stars Reviewed 15 May 2014
    For me as an artist, staying at Sam and Rebecca's cottage, inspired a number of drawings, photographs and watercolors. My husband was able to disconnect from electronic media and...
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    1 / 14
    5 of 5 stars (21) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    NEXT AVAILABLE SHORT OPENINGS AS LISTED BELOW: SPECIAL, UNIQUE STUDIO IN THE HEART OF WAILEA. YOU MIGHT PAY LESS, BUT YOU CAN'T GET MORE FOR YOUR MONEY! AUG 5 - 10 $88/NT + $80 CLNG + TAX 13.42% AUG 14-16 " " "... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 1 October 2013
    Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
    5 of 5 stars Reviewed 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 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 / 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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    • Pet-friendly
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    • x
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    • x
    About this property
    FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 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 4 May 2015
    I loved this studio. It was very nice space with a deck. It has a stackable washer/dryer. The bed was super comfortable and owners were responsive to my needs. At the time I was...
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    1 / 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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a recently renovated luxury first floor condo in Wailea's premier Grand Champions Villas. Our home is unit #103 on the east side of the complex. Spend your vacation enjoying this 1 bedroom, 2 bath unit that provides ample space to spread out,... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 23 April 2014
    I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
    5 of 5 stars Reviewed 11 September 2013
    I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
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    1 / 18
    4.5 of 5 stars (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    This ground floor, Wailea Ekahi condominium has an ocean view. There is a king bed in the master bedroom and queen sofa sleeper in the living room. Air conditioning in both the bedroom and living room, ceiling fans throughout, portable stereo with CD player, 2 TV’s and DVD player. There are linens,... View all property information
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    Wailea, Maui 96753
    4 of 5 stars Reviewed 7 May 2014
    This was our first trip to Maui so we weren't quite sure what to expect. All I can say is that we loved it! The condo worked out brilliantly with lots of space; very well equipped...
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    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Balcony
    • Ocean Views
    • Washer
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Relax and Enjoy this spacious and modern one bedroom two bathroom condo with high end remodel. This condo is on the second floor in a two story building so you have amazing vaulted ceilings and no one above you. This is a completely private one bedroom condo with your own private lanai. There are... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 6 August 2015
    We thoroughly enjoyed Kathleen's condo and her hospitality. The beds were comfortable. The condo had just been remodeled and was gorgeous. We could tell a lot of thought and...
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    About this property
    Special Spring 2016 Pricing - Please Ask. Wailea Ekahi Village 35B is where you want to be. It is the paradise you have been looking for. Walking through the landscaped grounds, you are surrounded by beautiful orchids, ginger, bougainvillea and hibiscus flowers. Both bedrooms are furnished with... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 15 September 2015
    We stayed at Wailea Ekahi in unit 35B in October and really really enjoyed it. . A favourite happy hour spot was the upper balcony. We loved the ground floor patio and ate our...
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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
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    • Mountain Views
    • Ocean Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We recently remodeled our condo with all new upgraded tumbled travertine-style flooring, new window shades and new furniture. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3 of the cost and not have to purchase every meal in a resort hotel? You'll have a... View all property information
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    Wailea, Maui 96753
    1 / 27
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Washer
    • Balcony
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Parking
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. Our condo has a terrific layout with the bedrooms being on opposite sides of the condo. Each has its own private washroom, flat screen TV and... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 18 September 2013
    Once again, I loved everything about this condo. Beautiful first class furnishings, close to wonderful beaches in Wailea & Makena, & great shopping. The extra touches like the...
    5 of 5 stars Reviewed 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 / 24
    5 of 5 stars (21) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Mountain Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located "down in front" on the water at Wailea Elua Village, this Second Floor AIR CONDITIONED Condominium has received a complete Custom-Designed Interior Renovation. Everything has been updated - flooring, furniture, artwork, lighting, and fixtures - including a fully upgraded kitchen with... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 24 September 2013
    This is the condo to rent! I spent a long time looking at condos on various websites and I feel so fortunate to have found this condo! The owners are easy to work with and...
    5 of 5 stars Reviewed 4 August 2011
    This was a very beautiful, upscale condo with a wonderful, well-stocked kitchen; there was a grill so we had 3 meals in and enjoyed dining on the lanai -- gorgeous view. It was...
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    1 / 14
    5 of 5 stars (5) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Satellite TV
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Spring 2016 Super Specials - Please inquire !! 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 dining... View all property information
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    Wailea, Maui 96753
    4 of 5 stars 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 / 29
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Note: *** Our calendar is always up to date. Low Season Rate (Apr 16 - Dec 15) $395.00 per night High Season Rate (Dec 16 - Apr 15) $450.00 per night Are you looking for a quiet peaceful alternative vacation experience away from the hotel zone but minutes away from South Maui's best beaches,... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 27 July 2014
    We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
    5 of 5 stars Reviewed 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 / 42
    5 of 5 stars (88) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. The Aloha Kai Suite is elegant and refined to the last detail--sophisticated furnishings and spectacular art. Formal entry hall. Spacious living room. Formal dining with... View all property information
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    Wailea, Maui 96753
    5 of 5 stars Reviewed 7 March 2016
    What can I say? Stayed with some friends and everything, from the booking with Susan, to the welcome at the resort, to the finishes in the unit itself, the hi-spec TVs, the ocean...
    5 of 5 stars Reviewed 11 August 2015
    We stayed at this condo with another family for seven nights. This home surpassed our expectations. It was immaculate and easily fit our two families of four. The kitchen was...
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    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Two bedroom Two bath, second floor condominium right on the Beach. It is perfect for two couples or a family of four. You are literally steps from the beach! This condominium is at the front of the building closest to the ocean making for spectacular views! Upgraded kitchen and baths, central air... View all property information
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    Wailea, Maui 96753
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Special Fall 2016 Rates ! 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 large flat screen TV, DVD player,... View all property information
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    Wailea, Maui 96753
    Wailea Holiday Rentals

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

    Things to do in Wailea

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

    Renting villas and condos in Wailea

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