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Vacation Rentals in Wailea, HI

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From
$695
Per Night
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1 / 44
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3 Bedrooms, 4 Bathrooms, Sleeps 10
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$356
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$369
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$290
Per Night
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1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Hot Tub
  • TV
  • Washer
  • Dryer
  • Microwave
  • Stereo System
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$145
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1 / 25
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Stove
  • Grill
  • DVD Player
  • Patio
  • Microwave
  • Dryer
  • TV
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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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From
$340
Per Night
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1 / 12
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Shared Outdoor Pool...
  • Linens Provided
  • DVD Player
  • Microwave
  • Waterfront
  • Air Conditioning
  • Internet Access
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This luxury condo was designed to mirror a Balinese tree house. Completely remodeled with Hi-Tech Appliances. 2nd floor unit ~ stairs. 4 dining seats on Lanai, 3 indoor bar stools. This renovated 1 BR/ 1 BA unit features Italian plastered walls, mango and concrete counter tops, koa wood... View all property information
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3 of 5 stars Reviewed November 17, 2011
The condo was just fine, truly just average. We rented from Kumulani Vacations. I notice that since our visit, the unit is no longer on vrbo so we could not review on the vrbo...
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From
$170
Per Night
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1 / 23
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Microwave
  • Refrigerator
  • Washer
  • Dishwasher
  • Dryer
  • Stove
  • VCR
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
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1 of 5 stars Reviewed September 27, 2014
I booked this condo in July as 3 of us are attending a conference. I was notified that my final payment was due, which I paid promptly. On Mon. I received a notification that my...
5 of 5 stars Reviewed April 3, 2014
We ran across this particular condo because we needed to fill in 3 additional days on our recent stay in Maui. The only regret is we didn't know about it earlier. The condo itself...
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From
$200
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 2
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Details Reviews (1) Make Inquiry
Amenities & Details
  • VCR
  • Microwave
  • Dishwasher
  • Stove
  • Washer
  • Patio
  • Grill
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • 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
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5 of 5 stars Reviewed September 15, 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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From
$785
Per Night
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1 / 19
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (7) Make Inquiry
Amenities & Details
  • Wi-Fi
  • DVD Player
  • Satellite TV
  • Air Conditioning
  • Hot Tub
  • Gym
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named with vaulted ceiling, HD TV, DVD, wireless internet and formal dining area. Tropical blue and turquoise colors convey a serene ambiance comparable to the pristine... View all property information
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5 of 5 stars Reviewed December 28, 2014
Definitely a great condo. Ho'oeli isn't a wonderful property. Pool is outstanding. Massage poolside-definitely get one! Mercedes is amazing. Condo has comfy beds, elevator if...
5 of 5 stars Reviewed July 23, 2014
Our vacation rental was clean, spacious, quiet and most importantly, had great views. If you are looking for a great family rental on your vacation, I highly recommend Ho'Olei!
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From
$190
Per Night
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1 / 11
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2 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$199
Per Night
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
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Details Reviews (7) Make Inquiry
Amenities & Details
  • TV
  • DVD Player
  • Washer
  • Dryer
  • Grill
  • Patio
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
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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5 of 5 stars Reviewed December 28, 2014
My husband and I stayed at this beautiful ohana for almost 3 weeks. Dennis and Cynthia thought of everything to make our stay comfortable and enjoyable. First, the cottage was...
5 of 5 stars Reviewed December 22, 2014
This beautiful cottage was very well kept (clean and modern) in a great location close to the beach and just a short drive from amenities, shops and restaurants. We had a...
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From
$240
Per Night
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1 / 35
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1 Bedroom, 3 Bathrooms, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Refrigerator
  • Microwave
  • Grill
  • Dishwasher
  • Stove
  • Dryer
  • TV
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We recently remodeled our condo with all new upgraded tumbled travertine-style flooring, new window shades and new furniture. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3 of the cost and not have to purchase every meal in a resort hotel? You'll have a... View all property information
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From
$250
Per Night
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1 / 8
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1 Bedroom, 2 Bathrooms, Sleeps 5
Details Reviews (17) Make Inquiry
Amenities & Details
  • Dishwasher
  • DVD Player
  • Parking
  • Dryer
  • Refrigerator
  • VCR
  • Patio
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Located on world famous Keawakapu Beach in Wailea, Ekahi Village is one of the most sought after locations. Our totally renovated condo offers complete privacy, but is only steps to the beach. Unwind after a day at the beach or pool by watching our 46' Sony Bravia flat screen with surround sound... View all property information
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4 of 5 stars Reviewed February 27, 2013
My husband and I stayed in this unit for 3 weeks another couple joined us for 2 weeks. The owner was easy to work with and provided all the needed information to make our stay...
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From
$390
Per Night
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1 / 14
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1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to Paradise. This 1 Bedroom /1 Bathroom condo up on the second floor is in the heart of the luxurious Wailea Ekahi beachfront resort surrounded by tropical gardens overlooking the Keawakapu Beach. With four separate swimming pools, lush grounds and beachfront pavilion, Wailea Ekahi is hard... View all property information
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From
$685
Per Night
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1 / 22
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • DVD Player
  • Hot Tub
  • Gym
  • Wi-Fi
  • Ceiling Fans
  • Satellite TV
  • Refrigerator
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Relax and spread out in more than 3300 interior feet of custom home with designer furnishings. The tropically furnished living area with vaulted ceiling offers HD TV, DVD, IPod dock, and wireless internet, all in an intimate yet spacious room. The gourmet kitchen is outfitted with a Wolf 30'gas... View all property information
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4 of 5 stars Reviewed January 26, 2014
Had a great stay at 24-6 Ho'olei and on Maui. The condo was very large, clean, and well appointed, everything we needed for a base of our stay. A 5 minute walk to the beach...
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From
$240
Per Night
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1 / 25
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Patio
  • Grill
  • Refrigerator
  • TV
  • Safe
  • Stove
  • Hot Tub
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Deluxe Gorgeous 2 bdrm 2ba luxury condo in Wailea, World's Best award-winning island of Maui Excellent condition and location. Minutes from everything; beaches, golf, tennis, shopping, restaurants, beach-side walks, luxurious pool and park-like grounds * IMPORTANT* Please check link for website at... View all property information
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From
$225
Per Night
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1 / 15
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1 Bedroom, Sleeps 2
Details Reviews (1) Make Inquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Stove
  • Hot Tub
  • Grill
  • Microwave
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Looking for a completely remodeled, gorgeous condo? Experience one of Wailea's finest........... EVERYTHING in this beautifully appointed unit is BRAND NEW and is professionally decorated. The ground floor condo features high end finishes and furnishings which include: beautiful custom walnut... View all property information
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5 of 5 stars Reviewed May 14, 2014
We travelled to Maui in March, stayed for two weeks in a lovely condo at Grand Champions, Wailea. We went with 10 other friends, who also rented condos there. The manager...
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From
$1,350
Per Night
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1 / 23
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Parking
  • DVD Player
  • Hot Tub
  • Microwave
  • Patio
  • Safe
  • Dishwasher
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to Nani Pulelehua ('Beautiful Butterfly'), a luxurious panoramic ocean view estate. 1.5 miles from beaches, dining and shopping. A perfect spot for adults & kids! So close to everything yet private and spacious, away from any crowds. Features 4 bdrms w/ 4 King beds (2 masters), + queen... View all property information
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From
$225
Per Night
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Inquiry
Amenities & Details
  • Refrigerator
  • Microwave
  • Stereo System
  • Gym
  • Dishwasher
  • Hot Tub
  • TV
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Pool closure notice: The pool will undergo renovations May 4 - June 8, 2015. During this time, there will be no access to the pool area. We are offering specials of 20% off all reservations at this time. Welcome to your home away from home! This beautifully remodeled 2-bedroom condo is a guest... View all property information
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4 of 5 stars Reviewed October 26, 2014
We cannot seem to branch out from the Palms at Wailea having stayed here a dozen or more times in the last decade. We have used many units for many purposes bring anywhere from 2...
2 of 5 stars Reviewed April 19, 2013
We stayed here April 11 - 20, 2013. This is actually a relatively nice unit. Great patio deck with pass through window from kitchen. Nice decorations and televisions. I like...
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From
$225
Per Night
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1 / 25
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (13) Make Inquiry
Amenities & Details
  • Washer
  • Stove
  • Dryer
  • Satellite TV
  • Ceiling Fans
  • Patio
  • Refrigerator
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is a large pool and hot tub that is perfect... View all property information
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From
$3,500
Per Night
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1 / 35
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • TV
  • DVD Player
  • Ceiling Fans
  • Grill
  • Dishwasher
  • Stereo System
  • Microwave
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Designed by world-renowned architect Tan Hock Beng, Hale Kumulani is a magnificent home built around a grass courtyard. Boundaries between indoors and out are blurred, with walkways connecting bedroom suites to the main living areas. Located directly across the street from the exquisite white sand... View all property information
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From
$210
Per Night
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Amenities & Details
  • Refrigerator
  • Microwave
  • Washer
  • Hot Tub
  • Dryer
  • Gym
  • TV
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Pool closure notice: The pool will undergo renovations May 4 - June 8, 2015. During this time, there will be no access to the pool area. We are offering specials of 20% off all reservations at this time. This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The... View all property information
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4 of 5 stars Reviewed August 2, 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 July 25, 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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From
$265
Per Night
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1 / 26
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • TV
  • DVD Player
  • Microwave
  • Grill
  • Dishwasher
  • Patio
  • Washer
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 December 18, 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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From
$410
Per Night
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1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (25) Make Inquiry
Amenities & Details
  • Refrigerator
  • Parking
  • Patio
  • Stove
  • Grill
  • Dishwasher
  • Safe
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautifully remodeled and updated, our 1500 sf 2-Bedroom luxury condo in Wailea Resort's popular ocean front Wailea Ekahi Village is a few steps from gorgeous Keawakapu Beach. Fall asleep listening to the sounds of the surf . We are about a 5 iron (level 1-2 min walk) from the beach and Ekahi’s... View all property information
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5 of 5 stars Reviewed November 16, 2014
Very nicely maintained and equipped, right down to the candles. No complaints - only compliments. The TV went out in one of the bedrooms and it was replaced the next day with a...
4 of 5 stars Reviewed August 19, 2014
Highly recommend this condo unit. would have given it an "excellent" if it had a good ocean view-- which it once did, until some new construction between it and the ocean...
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From
$209
Per Night
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1 / 30
1 Bedroom, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Stove
  • Washer
  • Dryer
  • Grill
  • Satellite TV
  • Patio
  • Ceiling Fans
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is a large pool and hot tub that is perfect for... View all property information
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From
$185
Per Night
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1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (6) Make Inquiry
Amenities & Details
  • TV
  • Washer
  • DVD Player
  • Dishwasher
  • Dryer
  • Hot Tub
  • Safe
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • 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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5 of 5 stars Reviewed September 18, 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 November 20, 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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From
$115
Per Night
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1 / 26
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Grill
  • TV
  • Washer
  • Microwave
  • Dryer
  • DVD Player
  • Parking
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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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5 of 5 stars Reviewed June 13, 2013
My boyfriend and I stayed at Wailea Grand Champions for a couple of nights and we loved it. The property is beautifully maintained and it is located very close to several great...
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From
$140
Per Night
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1 / 27
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Washer
  • Dishwasher
  • DVD Player
  • Hot Tub
  • Stove
  • TV
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
$175
Per Night
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1 / 29
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • OGG - Kahului: 14.9...
  • Cycling Trips
  • There Is A Golf...
  • Good Nightlife
  • Fishing Nearby
  • Beach Or Lakeside...
  • Number Of Bedrooms
  • There Are Tennis...
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 / 13
1 Bedroom, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Grill
  • Terrace
  • DVD Player
  • VCR
  • Hot Tub
  • Refrigerator
  • Gym
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Spring 2015 Specials - Please ask ! Grand Champions 122 offers a large flat screen TV, DVD Player and CD Player. The living room has air conditioning, ceiling fan and vaulted ceiling. There is a separate dining area. The lanai also has a table and chairs to enjoy the outside view. The kitchen is... View all property information
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From
$125
Per Night
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1 / 7
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • DVD Player
  • Dishwasher
  • Washer
  • Parking
  • Refrigerator
  • Patio
  • Stove
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
MARCH AVAILABILITY: Arrive March 29th, depart April 2nd = 4 nights $135 plus tax (13.416%) and $75 cleaning. Short stays: Arrive Mar. 5th depart Mar. 7th - Call or email for pricing APRIL AVAILABILITY: Arrive Apr. 8th, depart April 12th - Call or email for pricing This great one bedroom... View all property information
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5 of 5 stars Reviewed January 25, 2014
My partner and I came to Maui to run the Maui Oceanfront Marathon. We had booked a room at the Marriott for which the marathon had a room block. However, because we wanted to...
5 of 5 stars Reviewed February 3, 2013
Three of us (wife, toddler girl and myself) rented this place in early January. The condo is just the right size for us. We love the location. It's in an upscale area of Maui...
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From
$185
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1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Washer
  • Hot Tub
  • Safe
  • Dishwasher
  • Microwave
  • DVD Player
  • Refrigerator
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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. This spacious 1148 square foot condo has a great layout for privacy. The large bedrooms are on opposite sides of the condo with their own private... View all property information
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From
$995
Per Night
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1 / 32
3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Parking
  • TV
  • DVD Player
  • Microwave
  • Hot Tub
  • Safe
  • Dishwasher
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
'Wailea Beach Villas is the #1 Specialty Lodging in Wailea' - Trip Advisor 'Wailea Beach Villas is one of the top 100 hotels in the USA' - Conde Nast Readers Choice Award The Wailea Orchid is an amazing 3 bedroom / 3 full baths penthouse villa located in the prestigious Wailea Beach Villas.... View all property information
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From
$295
Per Night
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1 / 16
1 Bedroom, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Stove
  • DVD Player
  • Refrigerator
  • Parking
  • Stereo System
  • Safe
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Live large outdoors in this beautifully remodeled, lovingly cared for 1 bedroom, 2 bath condo with huge lanai. One of Ekahi's larger 1 bedroom floor plans, 10E features soaring Cathedral ceilings, tropical garden setting with good ocean and West Maui Mountain views a nearly level 2 minute walk from... View all property information
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5 of 5 stars Reviewed July 2, 2014
This was a beautiful Condo with all the amenities. It had a beautiful view of the garden an ocean. Great lanai to sit and have breakfast and dinner at. Even had a gas grill to...
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From
$199
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1 / 34
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Dryer
  • Stove
  • Washer
  • DVD Player
  • Grill
  • Parking
  • Microwave
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Wailea Ekolu is one of most sought after properties in Wailea as it is nestled on the Wailea Golf Course. The property has a quiet and private atmosphere as the buildings are spread out across the lush tropical foliage. Wailea Ekolu has two lovely pool areas as well as a large pavilion area for... View all property information
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From
$695
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1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Hot Tub
  • TV
  • Parking
  • Refrigerator
  • Microwave
  • Dishwasher
  • Grill
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • 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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From
$1,435
Per Week
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1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Refrigerator
  • Ceiling Fans
  • Dishwasher
  • Washer
  • Parking
  • Stove
  • Safe
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • 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. Our condo has has a great layout for two couples. Each couple has there own private... View all property information
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5 of 5 stars Reviewed December 16, 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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From
$395
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1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • DVD Player
  • Grill
  • Dishwasher
  • Patio
  • Refrigerator
  • Hot Tub
  • Washer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to our home! Enjoy the fantastic ocean views and luxury of our home in Wailea Elua Village - a gated, 24 acre, oceanfront community. Our home is perfectly situated in the center of the Wailea Elua Village property (Unit #701). We are 150 yards from Ulua Beach -- just a 90 second walk to... View all property information
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5 of 5 stars Reviewed August 6, 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...
5 of 5 stars Reviewed April 27, 2014
Stayed her with our 18 yr old daughter for a week -- everything was perfect. Kitchen couldn't have been better equipped, lanai as advertised was huge. Complex was quiet, well...
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From
$320
Per Night
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1 / 15
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Safe
  • Parking
  • Refrigerator
  • Stove
  • Grill
  • Microwave
  • DVD Player
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Completely remodeled, this is the spot you dream of when you think ocean front island luxury. Fall asleep listening to the waves. Sweeping, close in ocean views from every room- even the shower! Our exceptional 1090 sf 1+ bedroom, 2 bath condo is unique at Wailea Ekahi Village offering premier... View all property information
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5 of 5 stars Reviewed November 27, 2014
We finished a five week vacation in Australia & New Zealand and were looking for a condo we can rest & relax for a week,before going home to New York. Well we found it in 11E .It...
5 of 5 stars Reviewed July 1, 2014
Beautiful 1 bedroom 2 Bath condo. Fully stocked with everything needed from Beach Chairs and towels to all linens and appliances. Super clean and comfortable. The master bedroom...
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From
$4,500
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1 / 21
4 Bedrooms, 5 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Satellite TV
  • DVD Player
  • Internet Access
  • TV
  • Safe
  • Dishwasher
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
$895
Per Night
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1 / 42
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • TV
  • Microwave
  • DVD Player
  • Gym
  • Garage
  • Dishwasher
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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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5 of 5 stars Reviewed January 26, 2015
My family and I had a wonderful time on our vacation, and so much of that was due to this terrific condo. We actually arrived in Maui 1 day early, before the condo was ready, so...
5 of 5 stars Reviewed December 5, 2014
the first words out of my moms' mouth when we got inside the condo was that she had never seen a place like this in her 65 years!!! There was 3 generations of family on this...
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From
$175
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1 / 25
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Safe
  • Stereo System
  • Washer
  • Dishwasher
  • DVD Player
  • Microwave
  • Parking
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our beautifully renovated spacious 2 bedroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. The large air conditioned Master Bedroom features a king-size bed with high end linens and a large flat screen HDTV. There is also an iPod/iPhone charger and... View all property information
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5 of 5 stars Reviewed July 23, 2014
This home is absolutely everything you are looking for when staying in Maui. It has it all, location, privacy, amenities, comfort, security stay at what is considered an upscale...
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From
$265
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1 / 10
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (9) Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Microwave
  • Safe
  • Stove
  • Washer
  • TV
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • x
About this property
Welcome to our piece of Maui Paradise. We are the new (December 2010) proud owners of this wonderfully remodeled 1 bed 2 bath Ekahi Village Condo. Living on the U.S. East Coast, Maui is our Tropical escape from the cold winters and hot humid summers, we have fallen in love with South Maui's sun,... View all property information
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4 of 5 stars Reviewed September 8, 2014
The condo was very nice , well maintained with quality renovations. The BQ was electric and I am a chef so that was one thing I didn't like and the towels were not very clean. The...
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From
$195
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1 / 14
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • DVD Player
  • Dishwasher
  • Stereo System
  • Dryer
  • Stove
  • Washer
  • Parking
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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 December 11, 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 August 2, 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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From
$290
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1 / 19
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • TV
  • Refrigerator
  • VCR
  • Dryer
  • DVD Player
  • Stove
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
$230
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1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Hot Tub
  • Dishwasher
  • VCR
  • Stove
  • Dryer
  • Refrigerator
  • TV
  • Gym
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Grand Champions 123 is located in a quiet setting in Wailea. Large green belts, manicured grounds and wide golf course fairways abound. To the east, views of Mt. Haleakala, the world’s largest dormant volcano. To the west, the sparkling blue Pacific Ocean. A quieter, more peaceful resort, this... View all property information
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From
$1,795
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1 / 31
3 Bedrooms, 4 Bathrooms, Sleeps 6
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Amenities & Details
  • DVD Player
  • Microwave
  • Satellite TV
  • Terrace
  • TV
  • Ceiling Fans
  • Dryer
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Ocean Bliss is a stunning beachfront estate that provides the best of all worlds...Privacy and ocean access as the house borders South Maui's Polo Beach with it's golden sands and shallow swimming area on one side of the villa and a dramatic lava rock beach on the other side. The vistas of the sea... View all property information
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From
$250
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Refrigerator
  • Parking
  • Dishwasher
  • Stove
  • TV
  • Gym
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Pool closure notice: The pool will undergo renovations May 4 - June 8, 2015. During this time, there will be no access to the pool area. We are offering specials of 20% off all reservations at this time. This open and spacious premium condo at The Palms at Wailea will be ideal for your island... View all property information
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From
$139
Per Night
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1 / 24
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • DVD Player
  • Parking
  • TV
  • Washer
  • Hot Tub
  • Dryer
  • Dishwasher
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Unit 181 is located in the heart of the beautiful and serene Grand Champions Villas. On the edge of the Wailea Blue Golf course, this condo is great for the golfing couple looking for a tropical getaway. Large green belts, manicured grounds and wide golf course fairways abound. Nearby shopping,... View all property information
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From
$1,595
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1 / 7
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Dishwasher
  • Hot Tub
  • Grill
  • Microwave
  • Dryer
  • TV
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Spend your vacation at Ho'olei luxury villas at Grand Wailea on Maui! Located just minutes from the world-class Grand Wailea Resort Hotel & Spa on Maui's southern shore, each two-story villa offers a luxurious home in paradise. Every villa has three bedrooms and 3.5 baths with finely appointed... View all property information
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Wailea 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.