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Condos and resorts Wailea, HI

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All 228 Rentals in Wailea
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From
$6,028
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details Reviews (1) Make Enquiry
From
$1,025
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
66 photos Details Reviews (10) Make Enquiry
From
$308
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
19 photos Details Reviews (1) Make Enquiry
Also consider
Wailea Ekahi Village 29F Ocean Front
1 Bedroom, sleeps 4
$456 / night
Beautiful Maui Wailea condo in beachfront building
1 Bedroom, sleeps 4
$331 - $393 / night
Ekahi-2A Lower Village, Ocean Views and Sunsets
2 Bedrooms, sleeps 6
$468 - $599 / night
WOW !  WHAT A GREAT VIEW ! ---Great Reviews !
2 Bedrooms, sleeps 6
$450 - $582 / night
From
$371
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details Reviews (2) Make Enquiry
From
$147
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details Reviews (13) Make Enquiry
From
$2,110
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
78 photos Details Reviews (1) Make Enquiry
From
$502
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details Reviews (8) Make Enquiry
From
$285
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
$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
$398
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
35 photos Details Reviews (14) Make Enquiry
4 of 5 stars Reviewed 9 April 2013
We stayed here for five nights in January. There are a lot of really wonderful things about the unit - the location in Wailea, the beach access through a quick trail (less than 5...
1 of 5 stars Reviewed 26 June 2011
The title says it all. We had made our reservations 4 months prior to our arrival, but the owner decided she wanted to stay in her unit with her friends the same week were...
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From
$222
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details Reviews (7) Make Enquiry
From
$406
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 14 October 2014
Hospitality - very ok. The property had all the facilities described. Location ok. I liked best that it was quiet and clean.
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
$793
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
$200
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
26 photos Details Reviews (3) Make Enquiry
3 of 5 stars Reviewed 3 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
$450
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
26 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
$228
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
$336
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
$793
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details Reviews (18) Make Enquiry
From
$679
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 23 November 2012
My mother, wife, and I stayed here from Nov. 11th till Nov. 16th, 2012. This is a lovely and nice place you should definately consider staying when making a trip to Wailea, Maui...
5 of 5 stars Reviewed 13 January 2012
My thank you note to the owners: I just want to say thank you for opening up your Maui home to fortunate people such as us. Your home there is lovely! You did a beautiful job...
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From
$302
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details Reviews (9) Make Enquiry
4 of 5 stars Reviewed 9 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
$627
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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From
$1,135
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Reviews (5) Make Enquiry
From
$1,469
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
45 photos Details Reviews (1) Make Enquiry
From
$222
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
14 photos Details Reviews (14) Make Enquiry
5 of 5 stars Reviewed 12 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 3 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
$855
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 August 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
$222
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 15 May 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
$393
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
$268
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
$131
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
$131
Per Night
Studio, 1 Bathroom, Sleeps 2
14 photos Details Reviews (21) Make Enquiry
5 of 5 stars Reviewed 1 October 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 30 September 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
$285
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
$228
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
$137
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details Reviews (10) Make Enquiry
From
$274
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
21 photos Details Reviews (2) Make Enquiry
From
$291
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
$148
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
$405
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (1) Make Enquiry
From
$6,826
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!
See all reviews
From
$1,477
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
$131
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 26 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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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)
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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.