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Vacation rentals in Wailea, HI

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All 228 Rentals in Wailea
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From
$400
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details Reviews (2) Make Enquiry
From
$214
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
23 photos Details Reviews (1) Make Enquiry
From
$219
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details Reviews (1) Make Enquiry
Also consider inquiring on or booking these rentals
Ho'olei Beautiful Home, Close to Pool and Beach
3 Bedrooms, sleeps 8
$843 - $2,193 / night
Charming Private Studio!  Affordable Wailea
1 Bedroom, sleeps 2
$129 - $157 / night
Ekahi-2A Lower Village, Ocean Views and Sunsets
2 Bedrooms, sleeps 6
$461 - $590 / night
Elegantly Remodeled Condo w/ Expansive Ocean Views
1 Bedroom, sleeps 4
$292 - $315 / night
From
$782
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
44 photos Details Reviews (27) Make Enquiry
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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From
$224
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
21 photos Details Reviews (4) Make Enquiry
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
$415
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (1) Make Enquiry
From
$253
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
22 photos Details Make Enquiry
From
$214
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
17 photos Details Make Enquiry
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From
$236
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Make Enquiry
From
$168
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details Make Enquiry
From
$214
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
11 photos Details Make Enquiry
From
$219
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
13 photos Details Make Enquiry
From
$332
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
7 photos Details Make Enquiry
From
$219
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details Make Enquiry
From
$219
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 4 November 2011
We love staying at Ekahi Village condos. We have stayed here multiple times, this last time in 3C. What we love most is that there are no surprises, everything is exactly as...
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From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (5) Make Enquiry
4 of 5 stars Reviewed 2 August 2014
We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
4 of 5 stars Reviewed 25 July 2014
This was our first trip with our grandaughters. The location is ideal for the snorkling beaches with lifegaurds. The location is also close to all types of dining and fine...
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From
$196
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details Reviews (30) Make Enquiry
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
$236
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (5) Make Enquiry
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
$280
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details Reviews (34) Make Enquiry
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...
5 of 5 stars Reviewed 26 February 2012
My girlfriend and I throughly enjoyed this property. The peace and serenity offered is unique to the islands. Every morning you are awakened by the sweet sound of birds signing...
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From
$213
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
26 photos Details Reviews (24) Make Enquiry
4 of 5 stars Reviewed 18 July 2014
Our first trip here and we were very happy with the accommodation selected by our travel agent. The condo comfortably sleeps 6 adults The staff and surrounds are great we...
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From
$281
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (13) Make Enquiry
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
$495
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details Reviews (8) Make Enquiry
From
$219
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
14 photos Details Reviews (14) Make Enquiry
5 of 5 stars Reviewed 11 December 2013
Wonderful, wonderful studio condo on second floor. Super clean, and newly refurnished and redecorated including the lanai which was fabulous for BBQing in the evening and...
5 of 5 stars Reviewed 2 August 2013
Gorgeous condo with walking distance to gorgeous beaches with great snorkeling, newly renovated kitchen including everything from soy sauce to Tupperware, a small gas BBQ grill...
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From
$332
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details Reviews (2) Make Enquiry
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
$2,047
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (1) Make Enquiry
From
$197
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
26 photos Details Reviews (3) Make Enquiry
3 of 5 stars Reviewed 2 February 2012
This one-bedroom condo (with hide-a-bed couch in living room) was obviously recently updated - the kitchen, bathroom and bedroom all had nice, tasteful, simple furniture...
5 of 5 stars Reviewed 5 May 2011
I don't know about you, but if I wanted to stay in a resort with a million it other people and had a 3 mile treck to the beach or pool....I could stay anywhere! Valley Isle #302...
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From
$618
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details Reviews (33) Make Enquiry
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...
3 of 5 stars Reviewed 5 September 2012
We were very excited to stay in this unit at Makena Surf but had a very disappointing experience. Our hope is to prevent other families from having a similar experience. First...
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From
$281
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details Reviews (4) Make Enquiry
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
$129
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 25 January 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 3 February 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
$444
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
26 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 27 July 2014
We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
5 of 5 stars Reviewed 8 July 2014
The wife and I and are 3 children (9, 9 and 3) stayed here for 8 nights! Looked at many homes in Maui and man did I nail it with this one! Perfect location, perfect owners...
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From
$225
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details Reviews (3) Make Enquiry
From
$191
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details Reviews (5) Make Enquiry
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
$1,119
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Reviews (5) Make Enquiry
From
$298
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details Reviews (9) Make Enquiry
4 of 5 stars Reviewed 8 September 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
$782
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details Reviews (18) Make Enquiry
From
$450
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos 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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From
$219
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 16 December 2013
My wife and I stayed in unit 29 at the Grande Champions Golf Villas for two weeks in December, 2013. The property manager Kathleen was fantastic to deal with and responded...
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From
$270
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
21 photos Details Reviews (2) Make Enquiry
From
$259
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details Reviews (3) Make Enquiry
From
$5,943
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
27 photos Details Reviews (6) Make Enquiry
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Suitability

  • Wheelchair access (15)
  • Elder access (61)
  • Suitable for children (54)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Grill (188)
  • Internet (184)
  • All pools (162)
  • Air Conditioning (158)
  • Public pool (155)
  • View all amenities
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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.