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Vacation rentals in Wailea, HI

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All 229 Rentals in Wailea
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$402
Per Night
1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$220
Per Night
1 / 13
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1 Bedroom, 2 Bathrooms, Sleeps 2
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$237
Per Night
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Also consider inquiring on or booking these rentals
Beautiful 1 bedroom in Wailea - Nov/Dec/Jan stays
1 Bedroom, sleeps 2
$112 - $192 / night
Beautiful Modern Wailea! Remodeled & Affordable
1 Bedroom, sleeps 4
$135 - $226 / night
Beautiful Maui Wailea condo in beachfront building
1 Bedroom, sleeps 4
$327 - $389 / night
Wailea Ekahi Village 29F Ocean Front
1 Bedroom, sleeps 4
$451 / night
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$214
Per Night
1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed 15 September 2014
I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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$784
Per Night
1 / 44
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3 Bedrooms, 4 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed 12 April 2014
Our first trip to Maui, Hawaii for our Daughters wedding. We were a family of 8 (including grandparents).Plenty of room,Condo is immaculate, amazing, beautiful, photo's were...
5 of 5 stars Reviewed 30 December 2013
Upon our arrival, we immediately knew we hit the jackpot! The spacious condo was beautiful and full of every necessity needed for our vacation. The views from the lanai were...
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$225
Per Night
1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed 11 September 2014
Many people visit Maui every year with the idea of having grand island adventures. It's the perfect place for all kinds of outdoor fun. Whether you are in the mood for scuba...
5 of 5 stars Reviewed 7 August 2014
A month before moving to Oahu my daughter and I had the privilege of staying in this beautiful fully furnished cottage with every comfort of home. Meals on the deck while...
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From
$416
Per Night
1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$168
Per Night
1 / 25
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$214
Per Night
1 / 11
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2 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$243
Per Night
1 / 13
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$327
Per Night
1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$1,410
Per Night
1 / 22
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$333
Per Night
1 / 7
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1 Bedroom, 2 Bathrooms, Sleeps 3
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From
$220
Per Night
1 / 15
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$1,687
Per Night
1 / 71
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$225
Per Night
1 / 30
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 21 April 2014
This condo was incredible, clean, well equipped. We had access to the pool, jacuzzi, tennis courts, it was across the street from the medical conference I went to at the Marriot...
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From
$1,636
Per Night
1 / 81
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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From
$220
Per Night
1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$282
Per Night
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 5 November 2012
Since I was the vacation planner for 6 other people beside's myself, I was also charged with finding a suitable place for us to hang our hats at the end of each day. By a stroke...
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From
$428
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 5
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5 of 5 stars Reviewed 29 August 2014
This was a fantastic stay. The accommodation was booked through mauivacationadvisors.com. The agency represents many properties. They were a huge help, offering suggestions...
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From
$281
Per Night
1 / 20
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed 6 November 2014
Can't recommend this place enough. Looks exactly like the pictures, partial sunset view every night on the lanai with a glass of wine. Top end finishing, amenities galore. Beach...
5 of 5 stars Reviewed 18 December 2012
I've stayed in Maui several times and this time, rather than stay in a cramped hotel room in the middle of tourists, I opted to try something different. The property is even...
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$196
Per Night
1 / 32
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 6 October 2014
We stayed in unit 48 for 9 nights in mid-September. We were extremely pleased with our stay, and I'm hoping that this post is helpful for others. This unit was in much better...
3 of 5 stars Reviewed 2 April 2012
We've stayed in units in the Grand Champions complex before. Not on the beach, but an easy 3 minute walk to the Shops at Wailea....and easy beach access from the adjoining...
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From
$226
Per Night
1 / 11
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$237
Per Night
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed 26 October 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 19 April 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
$271
Per Night
1 / 21
1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$333
Per Night
1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 2
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3 of 5 stars Reviewed 17 November 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
$463
Per Night
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 30 September 2014
This is a well maintained, spacious two bedroom unit that was ideal for our family of four, with two girls aged 10 and 13. There was a short walk to the beach and pool, and the...
5 of 5 stars Reviewed 26 June 2014
Our party of two adult couples stayed for a week at 2A at the beginning of May, and thoroughly enjoyed this lovely and immaculately-maintained condo. The location allows easy...
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From
$209
Per Night
1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 18 September 2013
Once again, I loved everything about this condo. Beautiful first class furnishings, close to wonderful beaches in Wailea & Makena, & great shopping. The extra touches like the...
5 of 5 stars Reviewed 20 November 2012
The condo was beautifully furnished. We appreciated all the extras that made this stay so relaxing like the Tommy Bahama beach chairs, boogie boards, beach towels, & beach...
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From
$621
Per Night
1 / 20
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed 27 October 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 2 October 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
$192
Per Night
1 / 23
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1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
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1 of 5 stars Reviewed 27 September 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 3 April 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
$1,123
Per Night
1 / 32
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Enquiry
From
$282
Per Night
1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed 7 April 2013
We spent 8 wonderful nights in Grand Champions. Location was perfect, 5 minutes to Big Beach and Shops at Waliea. Condo was clean and tons of space. We had two teenage girls and...
5 of 5 stars Reviewed 27 January 2012
We stayed here in early December 2011 for 12 nights. There were 4 adults and 2 children ages 8 years and 21 months. The property was perfect and had everything for our needs...
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From
$5,963
Per Week
1 / 27
3 Bedrooms, 3 Bathrooms, Sleeps 6
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3 of 5 stars Reviewed 29 October 2014
We stayed here with a total of 3 couples. The condo is spacious (even for 6), well furnished and well appointed with kitchen and dining requirements. Two bedrooms had king sized...
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From
$197
Per Night
1 / 25
2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed 23 July 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
$5,963
Per Week
1 / 22
3 Bedrooms, 3 Bathrooms, Sleeps 8
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4 of 5 stars Reviewed 26 January 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
$259
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (3) Make Enquiry
From
$226
Per Night
1 / 14
1 Bedroom, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed 9 November 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 17 August 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
$259
Per Night
1 / 18
1 Bedroom, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed 7 May 2014
This was our first trip to Maui so we weren't quite sure what to expect. All I can say is that we loved it! The condo worked out brilliantly with lots of space; very well equipped...
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From
$784
Per Night
1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (18) Make Enquiry
From
$451
Per Night
1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (10) Make Enquiry
5 of 5 stars Reviewed 9 October 2014
My friends an i find the Grand Champions condos to be quiet an peaceful. It's close to three great golf courses and several good restaurants. We live in Honolulu, where we have...
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Suitability

  • Wheelchair access (16)
  • Elder access (60)
  • Suitable for children (41)
  • Pet friendly (0)
  • Smoking allowed (0)

Amenities

  • Grill (190)
  • Internet (183)
  • Air Conditioning (157)
  • Other outdoor space (146)
  • All pools (142)
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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.