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Vacation Rentals in Wailea, HI

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From
$125
Per Night
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1 / 7
1 Bedroom, 1 Bathroom, Sleeps 2
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From
$995
Per Night
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1 / 32
3 Bedrooms, 3 Bathrooms, Sleeps 8
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$695
Per Night
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1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$395
Per Night
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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
$895
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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
$785
Per Night
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1 / 19
3 Bedrooms, 4 Bathrooms, Sleeps 8
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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
$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
$139
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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
$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
$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
Bookings
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
$695
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1 / 44
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3 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (27) Make Inquiry
Amenities & Details
  • TV
  • Gym
  • Hot Tub
  • Dishwasher
  • Refrigerator
  • Safe
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 April 12, 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 December 30, 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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From
$210
Per Night
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1 / 14
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Refrigerator
  • Microwave
  • Grill
  • Parking
  • DVD Player
  • Washer
  • Dryer
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Renovated 1 bedroom / 2 bathroom upstairs end unit with high-end furnishings and decorations. View is towards the island of Lanai, the West Maui coastline, and Ma'alaea Bay. Oversized master bedroom has a King size bed with study and sitting area. Large living/dining room area that harbors a... View all property information
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4 of 5 stars Reviewed November 9, 2014
We had a great week at Wailea Ekahi, enjoying both the unit we rented and the location of the Ekahi resort. Would highly recommend for a couple or a family with young children...
4 of 5 stars Reviewed August 17, 2014
Skip and Mickey were fantastic from the beginning. They have taken special care to stock the condo with everything you might need for a relaxing, fun trip to the beach. From...
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From
$250
Per Night
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1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Parking
  • Dryer
  • Stove
  • DVD Player
  • Patio
  • Dishwasher
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Aloha Maui vacation planners, Welcome to beautiful Wailea, a Master Planned Community which ensures good community planning and utilizes design guidelines to help preserve Maui's sophisticated island environment. Grand Champions Villas is located in the heart of Wailea and nestled between The... View all property information
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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
$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
$275
Per Night
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1 / 14
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Stove
  • Dishwasher
  • Safe
  • Refrigerator
  • Dryer
  • Patio
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Aloha! Welcome to magical, mystical, mythical Maui. My intimate, meticulously maintained one bedroom two bath condo is located on the 15th hole of the legendary Wailea Old Blue Golf Course. If you are searching for a first class yet budget friendly Wailea Resort accommodation, you will find that... 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
$625
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (11) Make Inquiry
Amenities & Details
  • Grill
  • Washer
  • Safe
  • Hot Tub
  • Parking
  • Microwave
  • TV
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Polo Beach Club sits on quiet Polo Beach. It is a unique building located within feet of the beach. Our home is a completely remodeled 2 bedroom 2 bath unit. We always provide daily maid service and upon arrival you will receive a complimentary fruit basket. When you first enter our home look... View all property information
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5 of 5 stars Reviewed December 10, 2014
My wife and I have stayed in many locations in Hawaii in general and Maui in particular, but, overall, none can compare to the Polo Beach Club and in particular THIS unit. While...
5 of 5 stars Reviewed November 28, 2014
We had seen positive reviews for #408 Polo Beach Club and really loved the pictures of the unit, so we had high expectations when we arrived at the unit. I'll have to say that...
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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
$275
Per Night
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1 / 21
1 Bedroom, 2 Bathrooms, Sleeps 5
Details Reviews (14) Make Inquiry
Amenities & Details
  • Hot Tub
  • TV
  • Stove
  • Safe
  • Dishwasher
  • Patio
  • DVD Player
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Maui Rendezvous, Wailea Ekahi 33A, is a luxury (beautiful, romantic, and family friendly) 1,100 square-foot 1 bedroom 2 bath condo that sleeps 5. It is in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain... View all property information
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5 of 5 stars Reviewed September 13, 2014
We loved the condo and the owners are great. We also loved it as a base camp for exploring the island. Very convenient to other resorts and highways. They provide everything you...
5 of 5 stars Reviewed July 24, 2014
My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean...
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From
$130
Per Night
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1 / 25
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (19) Make Inquiry
Amenities & Details
  • Microwave
  • DVD Player
  • Parking
  • Dryer
  • Dishwasher
  • Ceiling Fans
  • TV
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
HI. TAX ID# W70092255-01 Great Deal for a luxury rental in wailea. Contact us soon LAST MINUTE SPECIAL - : NOV 19-21, 2NIGHTS, $125/NT. + 13.42% Hi. Tax + $90 cleaning fee OTHER OPENINGS: PLEASE SEE OUR STUDIO PROPERTY, #132551 '.....Since we could only rent your... View all property information
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5 of 5 stars Reviewed June 23, 2014
Condo was very clean and with chocolates upon arrival. Beautiful island décor and kitchen was well stocked with basics to prepare meals. Plenty of furniture to store your...
5 of 5 stars Reviewed June 21, 2014
We loved very minute of our stay in the "Secret Garden" apartment. The property is spotlessly clean, well-equipped and beautifully furnished. We enjoyed breakfasts on the lanai...
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From
$400
Per Night
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1 / 18
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • TV
  • Safe
  • Stove
  • Refrigerator
  • DVD Player
  • Microwave
  • Dryer
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Aloha! 29F is located in the lower village and has arguably the best view in Ekahi Village. This professionally remodeled unit comes with all the amenities of a five star hotel, yet all the comforts of home. 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 October 10, 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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From
$250
Per Night
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1 / 8
Payment Protection
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
$225
Per Night
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
$240
Per Night
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1 / 35
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1 Bedroom, 3 Bathrooms, Sleeps 4
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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
$115
Per Night
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1 / 14
Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Parking
  • Microwave
  • Dryer
  • Hot Tub
  • Patio
  • Washer
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
HI. TAX ID# W70092255-01 NEXT AVAILABLE SHORT OPENINGS AS LISTED ABOVE: SPECIAL, UNIQUE STUDIO IN THE HEART OF WAILEA. YOU MIGHT PAY LESS, BUT YOU CAN'T GET MORE FOR YOUR MONEY! SEE CALENDAR FOR NEXT AVAILABL DATES. Add $75 one time cleaning fee and 13.42% Hi.... View all property information
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5 of 5 stars Reviewed October 1, 2013
Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
5 of 5 stars Reviewed September 29, 2012
We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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From
$410
Per Night
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1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Stove
  • Dishwasher
  • Safe
  • Microwave
  • Washer
  • Grill
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 December 22, 2014
This was our 4th stay in Ekahi 2A. This year family from Rhode Island, Southern CA, Montana and Oregon all met in Kiehi and Wailea, but we had the best condo out of everyone...
5 of 5 stars Reviewed September 30, 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...
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From
$750
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1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • TV
  • Gym
  • DVD Player
  • Grill
  • Washer
  • Hot Tub
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
PLEASE NOTE: OUR CALENDAR APPEARS OPEN BECAUSE WE OWN 5 HOMES AT THE HO'OLEI RESORT. IN MOST CASES, I DO HAVE A HOME AVAILABLE! Come enjoy our Luxury Residence in what we call our Executive Model! This home is the Hibiscus Model, which is the largest home at Ho'olei (3,301 sq. ft. and a 686 sq.... View all property information
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5 of 5 stars Reviewed August 12, 2013
We stayed in unit 24-1. The accommodations were first class. There aren't enough words to describe the luxury. We took our adult kids and their children. There was lots of...
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From
$189
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1 / 22
1 Bedroom, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Patio
  • Ceiling Fans
  • Microwave
  • DVD Player
  • Refrigerator
  • Dishwasher
  • Washer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book 'Maui Revealed' and their website. These properties were chosen because of their superior quality and great rates! The fabulous Keawakapu Beach is just a short 10 minute stroll... View all property information
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5 of 5 stars Reviewed November 24, 2013
I helped my sister and brothers find these condos for our stay in Maui. It was shocking to our entire extended family how large and nice these condos are at the Palms of Wailea...
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From
$300
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1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Hot Tub
  • Stove
  • Washer
  • Stereo System
  • Refrigerator
  • Dryer
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Our second story 3 bedroom villa with 1383 feet, is located in the beautiful Grand Champion Complex, located in the resort area of Wailea. Our corner villa offers a panoramic view of the West Maui Mountains as well as the ocean. The villa also overlooks the seventh farway of the Wailea Blue... View all property information
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5 of 5 stars Reviewed June 15, 2014
This is one of the best condos we have ever had the pleasure to stay in while visiting Maui. I read numerous reviews which had stated how well stocked the condo was. I would...
5 of 5 stars Reviewed October 14, 2011
Just ended our 9-day vacation on Maui. The condo was perfect for our group of 4 adults and two girls under 10. Everyone thought the condo was very nicely decorated, nice...
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From
$750
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1 / 18
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Washer
  • TV
  • Parking
  • Stove
  • Grill
  • Hot Tub
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Trip Advisor Guests Describe L409 as 'Perfect & Well Worth the Money'. Visit our website for additional pictures to see why this villa is the most popular unit there based on travelers reviews. Luxurious 3000' Panoramic Oceanview Villa Available at Owner Direct Low Prices. This breath taking... View all property information
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From
$750
Per Night
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1 / 25
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Safe
  • Refrigerator
  • Gym
  • Grill
  • Microwave
  • Hot Tub
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This spacious, professionally decorated town home has all the comforts you expect from a five star experience. The world renowned Grand Wailea resort located across the street, offers a world class spa, shopping and beach. Whether you group has many children, adults or seniors, this home is... View all property information
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From
$220
Per Night
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1 / 17
1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Dryer
  • DVD Player
  • Safe
  • Microwave
  • Patio
  • Stove
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 November 14, 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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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
$390
Per Night
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1 / 14
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • 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
$629
Per Night
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1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Washer
  • Microwave
  • Stove
  • Refrigerator
  • VCR
  • Stereo System
  • DVD Player
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Reviews praise this 'EXCEPTIONAL OCEANFRONT CONDO' that's just a few steps to its soft sand beach! 'Sunsational' newly remodeled condo offers island living at its best in Maui's finest area. The penthouse is only available to ADULT NON SMOKERS... Enjoy Wailea-Makena and the resort's best... View all property information
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5 of 5 stars Reviewed August 12, 2013
My husband and 2 sons stayed in this beautiful condo last week. It is quite a place! Every attention to detail is incredible from the beginning correspondence from the owner until...
5 of 5 stars Reviewed July 7, 2013
Since our last review, we have stayed there twice. The owner has not only maintained the condo in pristine condition but has updated the master bedroom and bath. The owner is...
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From
$575
Per Night
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1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Dryer
  • Microwave
  • Grill
  • Stove
  • DVD Player
  • Washer
  • Hot Tub
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade was completed June 2008 resulting in a home away from home with only highest quality finishes.... View all property information
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5 of 5 stars Reviewed October 27, 2014
What can I not say about this Condo? Being from the UK, I did have some worries about booking directly via TripAdvisor with Jim and making payments to what could potentially be...
5 of 5 stars Reviewed October 2, 2012
We booked this condo through the web site www.makenasurf.com and dealt with Jim Osgood during the booking process. Mr. Osgood was quickly responsive to my initial inquiry about...
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From
$240
Per Night
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1 / 25
Payment Protection
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
$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
$725
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1 / 34
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Safe
  • Dishwasher
  • Grill
  • Dryer
  • DVD Player
  • Sauna
  • Gym
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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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From
$245
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1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • DVD Player
  • Grill
  • Dishwasher
  • Hot Tub
  • Stove
  • Ceiling Fans
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
WE MANAGE OTHER SIMILAR BEAUTIFUL CONDOS IN WAILEA. IF THIS IS NOT AVAILABLE PLEASE CALL OR EMAIL FOR AVAILABILITY! 808-385-1140 OR EMAIL: Info@MakenaWaileaVacations.com If you are looking for a perfect get away in paradise, this is it! This luxury Palms at Wailea unit is located near the... View all property information
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From
$225
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1 / 15
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1 Bedroom, Sleeps 2
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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
$335
Per Night
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1 / 19
1 Bedroom, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Ceiling Fans
  • Microwave
  • Satellite TV
  • Internet Access
  • Refrigerator
  • Air Conditioning
  • DVD Player
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Wailea Ekahi 14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home ! You will feel like you are on top of the world as you look out from the second floor onto the Greenbelt and over the blue Pacific Ocean. The... View all property information
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From
$3,500
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1 / 35
4 Bedrooms, 5 Bathrooms, Sleeps 8
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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
$265
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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
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1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
$185
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1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
$4,500
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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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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.