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Wailea

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Vacation Rentals in Wailea, Maui

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
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  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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.

 
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
Hawaii, Maui, Wailea Holiday Rentals
Ho'olei #12-3
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Special offer details »
Week:
4,490 AUD - 9,339 AUD
Minimum rental - 1 week
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Wailea Ekahi Village 29F Ocean Front
Slideshow
4.5 of 5 stars 3 reviews
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
282 AUD - 411 AUD
Minimum rental - 1 week
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Ho'olei #39-3
Slideshow
4.5 of 5 stars 5 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Special offer details »
Week:
5,208 AUD - 10,776 AUD
Minimum rental - 1 week
Check availability
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Also consider
Makena Surf...
821 AUD - 1,232 AUD / night
3 Bedrooms, sleeps 6
3 Bathrooms
Elua Village...
405 AUD - 498 AUD / night
2 Bedrooms, sleeps 5
2 Bathrooms
Professionally...
190 AUD - 257 AUD / night
2 Bedrooms, sleeps 6
2 Bathrooms
Beautiful...
159 AUD - 231 AUD / night
1 Bedroom, sleeps 4
2 Bathrooms
Amazing Wailea...
713 AUD - 1,432 AUD / night
2 Bedrooms, sleeps 6
2 Bathrooms
Hawaii, Maui, Wailea Holiday Rentals
WAILEA ELUA, #1603
Slideshow
4.5 of 5 stars 3 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 5
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
717 AUD - 816 AUD
Week:
5,022 AUD - 5,711 AUD
Minimum rental - 5 nights
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Palms at Wailea 1904
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
226 AUD - 318 AUD
Week:
1,580 AUD - 2,227 AUD
Month:
6,773 AUD - 8,005 AUD
Minimum rental - 1 night
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Ocean View, Remodeled, Stuff for the Kids, CLEAN
Slideshow
4.5 of 5 stars 3 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
257 AUD - 334 AUD
Minimum rental - 5 nights
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Grand Champions #36
Slideshow
4 of 5 stars 4 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
200 AUD - 262 AUD
Minimum rental - 5 nights
Check availability
Map unavailable
Palms at Wailea #1209 1 Bedroom 2 Bath  Sleeps 4.  Great Rates!
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
204 AUD - 276 AUD
Week:
1,430 AUD - 2,148 AUD
Month:
6,127 AUD - 8,282 AUD
Minimum rental - 1 night
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Hawaii, Maui, Wailea Holiday Rentals
NEW DISCOUNTED RATE@GRAND CHAMPIONS on WAILEA BLUE
Slideshow
4 of 5 stars 5 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Special offer details »
Night:
184 AUD - 323 AUD
Minimum rental - 4 nights
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Hawaii, Maui, Wailea Holiday Rentals
Palms at Wailea #1508
Slideshow
4.5 of 5 stars 10 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
256 AUD - 461 AUD
Week:
1,789 AUD - 3,226 AUD
Month:
7,666 AUD - 13,824 AUD
Minimum rental - 1 night
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Hawaii, Maui, Wailea Holiday Rentals
WAILEA ELUA, #2107
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
389 AUD - 462 AUD
Week:
2,723 AUD - 3,233 AUD
Minimum rental - 5 nights
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Beautiful Maui Wailea condo in beachfront building
Slideshow
4.5 of 5 stars 9 reviews
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
298 AUD - 354 AUD
Minimum rental - 1 week
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Hawaii, Maui, Wailea Holiday Rentals
WAILEA EKAHI, #34F
Slideshow
4 of 5 stars 6 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
405 AUD - 457 AUD
Week:
2,838 AUD - 3,197 AUD
Minimum rental - 5 nights
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Wailea Ekahi 1A
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
203 AUD - 292 AUD
Week:
1,422 AUD - 2,047 AUD
Month:
6,096 AUD - 8,515 AUD
Minimum rental - 5 nights
Check availability
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Hawaii, Maui, Wailea Holiday Rentals
Ekahi-2A Lower Village, Ocean Views and Sunsets
Slideshow
4.5 of 5 stars 8 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
416 AUD - 513 AUD
Minimum rental - 5 nights
Check availability
Show on map
Hawaii, Maui, Wailea Holiday Rentals
Awesome Ocean View - Beautiful 2 BR Maui Condo
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
385 AUD - 508 AUD
Week:
2,694 AUD - 3,556 AUD
Month:
11,546 AUD - 15,240 AUD
Minimum rental - 3 nights
Check availability
Show on map

Wailea Holiday Rental Advice

looking for luxury vacation rental near Wailea
Posted by ElizabethHansen, 2 Jan 2012
... looking for a very nice vacation rental somewhere around Wailea for at least a week, maybe two, next July. We'd like to be on or very near the beach and have access to a pool. We need three bedroom and at least two bathrooms, full kitchen with all the ... more
Wailea beach villas
Posted by MauiFreshChef, 17 Feb 2012
... a unit with your preferred vacation rental agency or owner and then read reviews for that particular unit (so many variable factors for each unit). Complex is huge and there will be some differences based on location and side of building. Also note distance to walk from front building or ... more
beachfront at Wailea
Posted by ChiSue, 26 Sep 2011
The vacation rental agency we employ has a site that compares amenities at the condo complexes where it rents units. It will give you an idea of pricing. Don't expect any big 'deals'. This is a season where many places are booked solid from Christmas to mid-April, at ... more
10 people to Maui
Posted by ChiSue, 8 Jan 2011
... every lodging in Hawaii, showing aerial views and providing reviews of the properties: www.wizardpub.com You might get a 'break' on several condos while renting via a real estate company or vacation rental agency. In West Maui look at Chase 'n Rainbows. In South Maui, look at Bello Realty ... more
South Maui is the best place for a 2nd home WSJ article
Posted by ChiSue, 12 Mar 2010
... Try these numbers (for a vacation rental condo): RE taxes on 849 sq ft condo -- $6000 Condo Assn. dues -- $5640 Tax on Rentals -- 13.42% -- at least another $4-5,000 Highest electrical rates in the nation. Among the highest gasoline prices. Everything has to be shipped in, so everything ... more
Mom of two needs HELP!
Posted by Mommyoftwogoodkids, 11 Oct 2009
... of attemping to find a vacation rental for my parents' 40 year anniversary, my sister and my two kids 5 and 7. They are very good kids- but like to play and splash in the pool. After days of searching for affordable rentals I start to read the reviews about ... more
Where to get groceries when staying in Wailea
Posted by MauiOC, 4 Oct 2009
... less expensive than going to the store as they can use CostCo and they don't get things that aren't on your list. To make life easier, http://www.mauiconcierge.com/ has expanded their personal services and are offering GROCERY STOCKING SERVICES (vacation rental provisioning) - see their SERVICES page ... more
Kai Malu?
Posted by Makena09, 26 Sep 2009
Kai Malu is not for vacation rentals. It is residential only with minimum 6 month leases. ... more
Posted by Julauf, 26 Sep 2009
... homes are not licensed for vacation rentals and the neighbors probably get a little miffed at owners who rent out their homes on a weekly basis. Your best bet would be to find a 3 bedroom condo maybe in South Kihei. I believe the Kamaole Sands has a few 3 ... more
Posted by swmarket, 26 Sep 2009
... Makena is correct then any vacation rental in this complex is illegal......and therefore quite chancy. Go woth a permitted, licensed, properly managed rental. Maui County cracked down on TVRs last year, and it continues to if there are complaints (like from neighbors). It's not a bargain if you ... more