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Vacation rentals in Wailea, HI

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All 220 Rentals in Wailea
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$221
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 2
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$231
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
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$262
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1 / 18
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1 Bedroom, 2 Bathrooms, Sleeps 2
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$808
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1 / 44
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3 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Our luxury ocean view town home is located in the gated community of Ho'olei, across the street from the Grand Wailea Resort. Our 3 bedroom/3bath home comfortably accommodates up to 10 guests. Our home features a finely appointed interior, private elevator, and attached garage. Built in 2007,... View all property information
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5 of 5 stars Reviewed 12 April 2014
Our first trip to Maui, Hawaii for our Daughters wedding. We were a family of 8 (including grandparents).Plenty of room,Condo is immaculate, amazing, beautiful, photo's were...
5 of 5 stars Reviewed 30 December 2013
Upon our arrival, we immediately knew we hit the jackpot! The spacious condo was beautiful and full of every necessity needed for our vacation. The views from the lanai were...
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$429
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
Beautifully furnished two bedroom Condo overlooking the Golf Course. The kitchen has 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 canopy bed. The accommodations... View all property information
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$6,592
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1 / 27
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Special Fall 2014 Rates - Please inquire ! Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named. Vaulted ceiling, HD TV, DVD, IPod dock, wireless internet, and formal dining area are a few of the many features. The... View all property information
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3 of 5 stars Reviewed 29 October 2014
We stayed here with a total of 3 couples. The condo is spacious (even for 6), well furnished and well appointed with kitchen and dining requirements. Two bedrooms had king sized...
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$221
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1 / 11
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2 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • Elder access
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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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$337
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1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Live luxuriously while on vacation! Beautiful Hawaiian art, travertine floors, granite countertops, tall bath vanities, and elegant new furniture make this condo a place of comfort and serenity. The two bedrooms are private, each with an en suite bathroom. The master bedroom offers a California... View all property information
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From
$302
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1 / 16
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
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About this property
Fall 2014 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 of... View all property information
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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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$231
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1 / 17
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
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  • Elder access
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About this property
Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 bath, 500 sq. ft. completely furnished cottage with full kitchen This cottage has it all. Spectacular furnishings and ocean views! Completely remodeled 1 bedroom cottage in Maui Meadows (Maui Meadows... View all property information
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$162
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1 / 25
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Beautiful 1 BR/2 bath 908 square foot interior + 200 square foot lanai overlooking thed7th fairway of the Blue Golf Course in exclusive Wailea Maui. Maui's best beaches, top notch dining, golf and tennis are 5-10 minutes walking distance. Enjoy sunsets and ocean views from lanai! Our completely... View all property information
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$1,453
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1 / 23
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Mountain Views
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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About this property
** $$$ DISCOUNTS for SPRING 2015! Rate is based on number of guests and nights. Please inquire now! Great for family vacation/reunions and adult getaways! Welcome to Nani Pulelehua ('Beautiful Butterfly'), a luxurious panoramic ocean view estate. 1.5 miles from beaches, dining and shopping. A... View all property information
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From
$343
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1 / 7
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1 Bedroom, 2 Bathrooms, Sleeps 3
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Over 1100 square feet of an exquisite & total remodel of our one bedroom, two bath condo in Wailea, Maui, HI provides a fabulous vacation spot as well as our Maui winter home. First floor, designer furnished with central AC, select comfort sleep number king bed, walk in showers, sophisticated AV... View all property information
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From
$233
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • 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
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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...
4 of 5 stars Reviewed 25 July 2014
This was our first trip with our grandaughters. The location is ideal for the snorkling beaches with lifegaurds. The location is also close to all types of dining and fine...
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$2,151
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1 / 78
3 Bedrooms, 3 Bathrooms, Sleeps 5
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  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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About this property
Reserve this villa H501 Wailea Paradise, set on the top floor in the premiere corner location within Wailea Beach Villas, with the best views in all of Wailea Resort, and receive all of the following newly expanded and enhanced benefits (and more) now!
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From
$231
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1 / 46
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
Unit #805 has a fully equipped kitchen, AC in the living room, guest bedroom, and master bedroom. The unit is equipped with a washer and dryer. The condo has a California king size bed in the master bedroom and two twin beds that can be made into a king in the guest bedroom. This property features... View all property information
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4 of 5 stars Reviewed 22 December 2013
Have stayed in several of the other key areas in Maui over the years...first time in Wailea and liked this location the best hands down. Condo and the whole complex very clean...
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From
$398
Per Night
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1 / 18
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Grill
  • Hot Tub
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • x
  • ?
  • Wheelchair access
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About this property
About this condo: Wailea Elua Village #307 is a spacious two bedroom, two bath oceanview condo with a king bed in the master bedroom, 2 twins in the guest bedroom and a sofa sleeper in the living room. It's located in the oceanfront area of the Wailea Elua Village property and has a large lanai... View all property information
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From
$843
Per Night
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1 / 60
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (14) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Wheelchair access
  • Elder access
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About this property
M111 Island Oasis Villa at Wailea Beach Villas provides two California king bedrooms, a third den bedroom sleeping space with queen bed and two marble bathrooms. This beautiful villa has more than 1,900 square feet of indoor living, that features elegantly contemporary 'Tommy Bahama' style decor,... View all property information
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5 of 5 stars Reviewed 17 January 2012
Spending our 35th anniversary here, in the beautiful Island Oasis Villa, could not have been more perfect. The owners of this villa know what they’re doing. Heavenly beds...
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$512
Per Night
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1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Grill
  • Hot Tub
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
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About this property
Notes from the Owners: We love relaxing on our large, sunny lanai with its spectacular panorama of ocean, plumeria and palm trees, and the west Maui mountains in the distance. It feels like it is our yard! It is just a short walk to a magnificent beach. Listening to the chorus of birds in the... View all property information
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From
$872
Per Night
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1 / 22
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dryer
  • Hot Tub
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Ho'olei is located in the center of the best resort on the best island in the world. With its sunny, temperate climate, variety of activities, upscale amenities and excellent design, Ho'olei is a truly exceptional retreat to enjoy year round. This is one of the finest units within this brand... View all property information
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From
$330
Per Night
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1 / 42
2 Bedrooms, 3 Bathrooms, Sleeps 4
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • x
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  • Wheelchair access
  • Elder access
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About this property
Unit #314 at Wailea Ekolu is the one of the most outstanding properties at Wailea Ekolu. This deluxe unit is a beautifully remodeled 2 story town house with 1489 sq ft of living space. This 2 bedroom 2.5 bath condo features great ocean views, a downstairs patio and an upstairs ocean view lanai... View all property information
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3 of 5 stars Reviewed 21 July 2014
We just came back from a weeks vacation here and I have to say that this is in a great location. The unit is located in a quiet area at the bottom of the complex on the golf...
5 of 5 stars Reviewed 9 April 2014
We could not be happier with our stay in unit #314!!! The location is great and the ocean view from the lanai is breathtaking! The kitchen has everything you will ever need and...
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From
$430
Per Night
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1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Wailea Ekahi - Nicely appointed 2 bedroom, 2 bath condo with garden and partial oceanview in the Upper Village over looking the top pool. Kitchen along with Masterbath was just freshly renovated. There is a King, 2 twin beds and a queen sofa sleeper and 3 separate lanais with a gas bbq on the... View all property information
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From
$279
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1 / 21
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
About this property
We recently remodeled our condo with all new upgraded tumbled travertine flooring and tropical faux painting through out. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3rds 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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From
$291
Per Night
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1 / 11
1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
Wailea Ekahi Village - 1 bedroom, 2 bath condo with a calming garden view located in the Upper Village. Features a freshly remodeled kitchen, new King size bed, sofa sleeper, air conditioning, complimentary Wifi and bbq on your lanai. TAT #W 06219089-01 Additional amenities include: games, gas... View all property information
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From
$267
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
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About this property
Look no further! This open and spacious premium condo at The Palms at Wailea will be ideal for your island getaway! Major renovations throughout, a partial ocean view, and central A/C* are just some of the features of this gorgeous 2-Bedroom condo. Pride in ownership is apparent when entering this... View all property information
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From
$465
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1 / 18
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • 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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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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$231
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1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Relax in the luxury and convenience of being in a world class resort, but enjoy the privacy and beauty of our fabulous 2 bd/2ba ground floor 'home away from home' that fronts the 7th Fairway of the famed Wailea Blue Course. Our spacious 1100 sq ft. unit has a tropical decor with world-class art... View all property information
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5 of 5 stars Reviewed 7 November 2011
The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea, the...
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From
$227
Per Night
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1 / 14
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
Located on the second floor, this studio offers stunning ocean views! It is furnished with a queen size bed, new flat screen TV and DVD, full kitchen, washer/dryer, air conditioning and ceiling fan, and a gas grill on the lanai. A fully remodeled kitchen, bath and dressing area sets our Ekahi... View all property information
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5 of 5 stars Reviewed 11 December 2013
Wonderful, wonderful studio condo on second floor. Super clean, and newly refurnished and redecorated including the lanai which was fabulous for BBQing in the evening and...
5 of 5 stars Reviewed 2 August 2013
Gorgeous condo with walking distance to gorgeous beaches with great snorkeling, newly renovated kitchen including everything from soy sauce to Tupperware, a small gas BBQ grill...
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$308
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1 / 26
1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautifully remodeled 1 bedroom 1.5 bath Ekahi Townhouse Condo. Enjoy outdoor living on our large ground floor lanai with peaceful ocean views just 20 seconds from a quiet pool or take breakfast or year round sunset breaks on the upstairs lanai with sweeping ocean views. Completely remodeled in... View all property information
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5 of 5 stars Reviewed 18 December 2014
The condo was everything we hoped it would be. It was very spacious, well maintained and equipped. We didn't even need the air conditioning! It tended to be a little noisy...
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$512
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1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Grill
  • Hot Tub
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
NEW TO OUR PROGRAM! UPDATES & IMPROVEMENTS ... Wailea Elua Village #2010 is located on one of the buildings corners, giving you ocean views and property from the master lanai and the main lanai which may also be accessed via the guest bedroom. Recently added to the condo area large new flat screen... View all property information
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From
$1,265
Per Night
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1 / 37
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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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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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From
$337
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1 / 19
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
1 bedroom 2 bath unit, recently remodeled with high end finishes. Vaulted ceilings create bright, spacious surroundings with plenty of room for the whole family. The master bedroom has a cal king bed with a private bath and dressing area. There is also a private lanai off the bedroom.The living... View all property information
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From
$296
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1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
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About this property
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 guarantees you'll... View all property information
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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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From
$320
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Mountain Views
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • x
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  • Wheelchair access
  • Elder access
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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
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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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From
$231
Per Night
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1 / 35
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua Beaches are just a 10 minute stroll down the hill from... View all property information
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From
$203
Per Night
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1 / 29
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • x
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  • Wheelchair access
  • Elder access
  • x
About this property
Can't find a better location - in the lower tier near the beach but far enough from the road for peaceful dreams. Immediately across from Kamaole III Beach park, this lovingly cared for condo has been upgraded and offers a semi-private 3rd sleeping area in the loft. Perfect for two couples (you... View all property information
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From
$185
Per Night
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1 / 31
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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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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From
$477
Per Night
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
DIRECT PANORAMIC OCEAN VIEWS. IF OTHERS DON'T SHOW IT, CHANCES ARE THEY DON'T HAVE IT. THE PHOTO TO THE LEFT TAKEN IN THE DINING ROOM. 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 Queen... View all property information
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5 of 5 stars Reviewed 30 September 2014
This is a well maintained, spacious two bedroom unit that was ideal for our family of four, with two girls aged 10 and 13. There was a short walk to the beach and pool, and the...
5 of 5 stars Reviewed 26 June 2014
Our party of two adult couples stayed for a week at 2A at the beginning of May, and thoroughly enjoyed this lovely and immaculately-maintained condo. The location allows easy...
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From
$459
Per Night
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1 / 29
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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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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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From
$680
Per Night
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1 / 27
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Special Fall 2014 Rates ! Please ask. Wailea Ekahi Village 53C is a fully renovated, 2 bedroom/2.5 bath townhouse with ocean views from the upstairs bedrooms and private downstairs lanai. It has 1575 sq. feet of living space. The master bedroom suite offers a king bed, sitting area, TV, DVD, a/c... View all property information
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From
$512
Per Night
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1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful three bedrooms, two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated in the fall of 2010 with granite throughout, stainless steel appliances, new carpet, paint and furniture. The living area is a large open floor plan with ceiling fans and... View all property information
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5 of 5 stars Reviewed 9 October 2014
My friends an i find the Grand Champions condos to be quiet an peaceful. It's close to three great golf courses and several good restaurants. We live in Honolulu, where we have...
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From
$273
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (37) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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  • ?
About this property
You will 'LOVE OUR MAUI CONDO!' Unit 166… PLEASE NOTE THAT FLIPKEY HAS MADE CHANGES TO THEIR SITE. PLEASE INQUIRE DIRECTLY TO THE OWNER FOR ACCURATE RATES AND POLICIES. Jackie@LoveOurMauiCondo.com Completely remodeled and redecorated, our unit is CLEAN & QUIET! Our 2 bedroom/ 2 bath Ocean &... View all property information
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5 of 5 stars Reviewed 26 January 2014
My husband and I, along with our 1 year-old daughter, stayed at this condo for a week Jan 14 - 21, 2014. The condo was clean and very well appointed. The lanai overlooks the...
5 of 5 stars Reviewed 6 September 2013
The photos are accurate and show a beautifully decorated home, but they don't show you how well stocked this home is. It's not "just a rental" with low quality/bare minimum...
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From
$163
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1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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From
$366
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
Wailea Ekahi 16B is located on the First floor with Ocean and Green Belt views. This Totally Remodeled Studio Condo is Beautifully furnished with Custom Bamboo Cabinets and Beautiful Tile throughout. New Queen Bed, Full First Class Kitchen, A/C, Ceiling fan, new Flat screen TV and Private lanai.... View all property information
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4 of 5 stars Reviewed 27 November 2014
Great location ..... condo well set-up ....would reccommend having "basics" in kitchen eg. salt &pepper, oil, flour,sugar,tea or coffee,foil .... we have stayed in other condos...
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From
$5,232
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1 / 21
4 Bedrooms, 5 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Slip into your own personal haven on the south coast of Maui. Home to the most discerning guests, Andaz Maui at Wailea's oceanfront, residential-style beach villas offer a secluded hideaway, just steps from the sands of Mokapu Beach. With the ocean as your backdrop, entertain on your own outdoor... View all property information
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From
$529
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1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Special Fall 2014 Rates ! Please inquire. Beautifully decorated three bedroom two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated the summer of 2011 with granite throughout, stainless appliances, new carpet, paint and furniture. The living area is... View all property information
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From
$267
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1 / 13
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Fall 2014 Discounted Rates. Please ask ! This second floor property has a fabulous view, charm, and is very convenient to the pool. Is is comfortably furnished with rattan. The livingroom area has ceiling fans both by the sofa and dining area as well as air conditioning. There is a flat screen TV... View all property information
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From
$231
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1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The nearby Ulua and Mokapu Beaches are a quick drive down the hill from The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming pools, sundecks, spa tubs, restrooms, showers and... View all property information
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5 of 5 stars Reviewed 21 April 2014
This condo was incredible, clean, well equipped. We had access to the pool, jacuzzi, tennis courts, it was across the street from the medical conference I went to at the Marriot...
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From
$256
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1 / 17
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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
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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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$843
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
WAILEA BEACH VILLA PENTHOUSE #306 (LUXURY 2 BR + DEN + 2 BA) PANORAMIC OCEAN VIEWS!!! LUXURY AND EXCLUSIVE 2 BR + DEN. NOW OFFERED AT AN AMAZING RATE!!! LOOK NO FURTHER! THIS IS THE NEWEST EXCLUSIVE, LUXURY WAILEA BEACHFRONT CONDO OFFERED AT AN AMAZING RATE!!! OVER 1900 SQ. FT + LANAI + BBQ... View all property information
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Wailea Vacation Rentals

Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

A Wailea Vacation

No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

Family-Friendly Wailea

From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.