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Condos and resorts Wailea, HI

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All 228 Rentals in Wailea
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From
$829
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
60 photos Details Reviews (14) Make Enquiry
From
$372
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details Reviews (2) Make Enquiry
From
$1,138
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
77 photos Details Reviews (7) Make Enquiry
Also consider
Totally renovated, closest to the beach!
1 Bedroom, sleeps 5
$286 - $400 / night
Wailea Ekahi 11f:  Ocean View/Remodel 2 BR Condo
2 Bedrooms, sleeps 4
$515 - $686 / night
Wailea, Maui , Hawaii The Palms Deluxe #706
2 Bedrooms, sleeps 6
$275 - $429 / night
Wailea Ekahi 7G Luxury Ocean Front S Maui Condo
1 Bedroom, sleeps 3
$389 - $515 / night
From
$228
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
50 photos Details Reviews (6) Make Enquiry
4 of 5 stars Reviewed 23 December 2013
Have stayed in several of the other key areas in Maui over the years...first time in Wailea and liked this location the best hands down. Condo and the whole complex very clean...
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From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (13) Make Enquiry
5 of 5 stars Reviewed 6 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
$503
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (6) Make Enquiry
From
$6,046
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 27 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
$6,846
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 24 July 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
$228
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details Reviews (13) Make Enquiry
From
$240
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
$452
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
29 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 28 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 9 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
$407
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 18 July 2014
Has been nice every time at this property. Although Room 33 faces to a parking lot, it was quiet and clean, and good to relax. Other type of the rooms such as a golf course or...
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From
$223
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details Reviews (7) Make Enquiry
From
$795
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 31 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
$469
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (14) Make Enquiry
5 of 5 stars Reviewed 1 October 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 27 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
$229
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (5) Make Enquiry
4 of 5 stars Reviewed 3 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
$337
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details Reviews (2) Make Enquiry
3 of 5 stars Reviewed 18 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
$269
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (21) Make Enquiry
4 of 5 stars Reviewed 15 May 2014
This was our first stop on our trip to the Hawaiian Islands and we wish we could have stayed longer. The condo was spacious and well appointed with almost everything you would...
5 of 5 stars Reviewed 26 September 2013
I stayed at the Grand Champions Villa for five nights and let me tell you WOW!!! It was so comfortable and amazing. You wake up in the morning and you have this fantastic view of...
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From
$2,082
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (1) Make Enquiry
From
$1,138
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Reviews (5) Make Enquiry
From
$795
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details Reviews (18) Make Enquiry
From
$149
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
25 photos Details Reviews (19) Make Enquiry
5 of 5 stars Reviewed 24 June 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 22 June 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
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 14 June 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
$228
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (16) Make Enquiry
5 of 5 stars Reviewed 8 November 2011
The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea, the...
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From
$685
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 13 August 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 8 July 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
$1,473
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
45 photos Details Reviews (1) Make Enquiry
From
$136
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
7 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 31 July 2014
Our family of four stayed at this condo for five days in July. It was a comfortable and pleasant home away from home. Pros: great price for Wailea area, very responsive owner...
5 of 5 stars Reviewed 25 November 2013
We had an awesome stay in this very spacious condo within this complex which is quiet and well served with pools and lovely tropical gardens. The free wifi was a bonus and TV in...
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From
$223
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 17 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
$137
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details Reviews (10) Make Enquiry
From
$303
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details Reviews (25) Make Enquiry
5 of 5 stars Reviewed 1 October 2014
The condo was beautiful and had all the amenities we could ask for. The grounds were well maintained and had several pools to choose from. The beach was close and excellent. I...
5 of 5 stars Reviewed 30 September 2014
It was wonderful.... Great location and VERY clean. We loved it and will return to this same condo. thanks, Greg
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From
$217
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
17 photos Details Reviews (3) Make Enquiry
From
$292
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 November 2011
We booked this condo for 8 days. It was everything that had been described to us and more. The view was fantastic. Everything we needed was there, all we had to bring was our food...
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From
$229
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details Reviews (9) Make Enquiry
4 of 5 stars Reviewed 18 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...
5 of 5 stars Reviewed 16 June 2013
This was our first visit to Maui and Skip and Mickey's condo was the perfect home away from home. They have it stocked with everything we needed for the beach - beach chairs...
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From
$257
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details Reviews (18) Make Enquiry
3 of 5 stars Reviewed 24 March 2014
We are just finishing up our stay at the Palms 1902. We thought the layout was great although the wall of shutters for the second bedroom doesn't do a lot for noise level in the...
3 of 5 stars Reviewed 22 October 2013
It was my 1st time renting a condo, typically We have stayed at the resorts. The condo made sense since my husband and I were sharing a place with my in-laws. The condo itself...
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From
$286
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 5
21 photos Details Reviews (14) Make Enquiry
5 of 5 stars Reviewed 14 September 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 25 July 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
$395
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 26 July 2014
Beautiful ocean view from balcony, living room and kitchen. My family loved unit # 306. Condo was better than photos. Very comfortable for a family of 5. Beds were comfortable...
5 of 5 stars Reviewed 20 July 2014
My husband, daughter, sister and brother-in-law rented Unit 306 at Polo Beach Club in Wailea, Maui. It was a wonderful experience! We were on the 3rd floor with a corner unit that...
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From
$1,253
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
78 photos Details Reviews (1) Make Enquiry
From
$1,315
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
83 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 15 August 2014
We rented Castaway Cove, Unit C201 at the Wailea Beach Villas on Maui in July 2014. This unit is managed by Tropical Villas Vacations. Our first visit to Maui and "wow" what a...
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From
$1,481
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
75 photos Details Reviews (8) Make Enquiry
5 of 5 stars Reviewed 31 October 2013
Very spacious, perfect for a family. This villa is finished with high quality furniture/appliances etc. it had everything you need and more! the property is secure, quiet and...
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From
$629
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details Reviews (33) Make Enquiry
5 of 5 stars Reviewed 3 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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Suitability

  • Wheelchair access (15)
  • Elder access (60)
  • Suitable for children (58)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Grill (187)
  • Internet (184)
  • All pools (162)
  • Air Conditioning (158)
  • Public pool (155)
  • View all amenities
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Wailea Holiday Rentals

If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.

Things to do in Wailea

Obviously you will be wanting to hit the beach in Hawaii, and there are many from which you can choose, such as Keawakapu Beach, surrounded by golf courses. If you don't want to spend all your time lying on one of the many south-facing beaches but aren't quite brave enough to go and climb a volcano, Wailea has many things to do for all ages, from playing golf and tennis to the inevitable shops and restaurants, all in an incredible Pacific climate. Wailea is fairly sparsely populated, with around 6,000 inhabitants, so you can also have a great time exploring the countryside nearby.

Renting villas and condos in Wailea

Wailea Resort is a wonderful place to visit and stay, but its planning is a bit contrived - the Wailea Community Association issue guidelines for new buildings aiming to preserve the island feel of Maui. With the additional aim of low population density, this does mean that prices even for holiday rentals may be higher than in other parts of the Hawaii island chain. But with the scary prices charged by hotels, and the extra flexibility associated with renting your own villa or condo for your family, Wailea holiday rentals still represent fantastic value for money. With air conditioning thankfully coming as virtually standard, and difficult choices of whether you'd prefer views of a volcano, a golf course, or perhaps a beach, it's an idyllic place to enjoy a great family holiday. And if you are looking for a low cost Pacific break, nothing beats buying local produce and cooking it up in your very own kitchen for the week, rather than relying on a hotel's expensive restaurants.