Vacation Rentals in Wailea, Hawaii
Wailea, Hawaii Vacation Rentals and Tourism
Unless you’re planning to book one of the Wailea vacation rentals found here, be prepared to cash in all your savings for a trip to South Maui. This beautiful part of Hawaii is a favorite spot for beachgoers and golfers, because the weather simply couldn’t be better here – but that also means plenty of fancy restaurants and upscale resorts are eager for you to spend money on them. If you want to enjoy all that Wailea has to offer and still stay within budget, turn to Wailea beach rentals!
- While you're here, check out our full and free Wailea Travel Guide.
Just south of Wailea is Makena Beach, which is ideal for swimming! The Wailea Beach Walk is also a must-see and must-do; take a stroll along this mile-and-a-half long stretch of land and catch glimpses of boogie boarders, swimmers, boaters, and maybe even whales! In addition to the amazing beaches, a Wailea vacation rental comes in handy because of the area’s equally amazing golf courses. Since the championship courses are so expensive, it’s a good idea to save money with a vacation rental in Wailea, HI. Enjoy the same convenience and wonderful location of a resort hotel, without spending all your dough! Don't forget that your Wailea beach vacation rental will likely feature a full kitchen, so there's no reason to waste money in restaurant after restaurant. Wailea vacation rentals have made it easier than ever for regular Joes to visit South Maui; in the past, when hotels ruled, only the wealthiest could vacation here.
But just because you’re saving money, doesn’t mean you have to deny yourself luxury. It’s not hard to find a great Wailea luxury beach condo for your family getaway or romantic honeymoon!
No matter what you’re looking for – monthly vacation house rentals in Wailea, Maui, or pet-friendly beachfront condos, or cheap, casual villas, better look here, before you look anywhere else. A great deal and a great vacation await you in Wailea!
Wailea Vacation Rental Deals
If you're lucky enough to be coming to Wailea for you next vacation, you are in for a huge savings on your Wailea rental home. Stay in an affordable Wailea vacation condo, villa, or beach house that is not only spacious but budget-friendly. Wailea vacation rentals accommodate any size group, so bring the whole family or just come get away with that special someone. No matter who you're with, we don't want you worrying about money, so that's why you can get a good deal even last minute on Wailea vacation rentals. Every vacation will cost, but staying in Wailea vacation rentals won't cost as much!
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$20 off = $140 per night
- bedrooms 2
- community Grand Champion Villa
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$160
- $300
/nt
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$20 off = $179 per night
- bedrooms 2
- community Wailea
- rental type Condo
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- sleeps 6
- baths 2
- rates (USD)
$179
- $325
/nt
- bedrooms 2
- community WCA-Grand Champions
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$235
- $315
/nt
$1,645 - $2,205 /wk
- bedrooms 2
- community
- rental type Cottage
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- sleeps 4
- baths 1
- rates (USD)
$650
- $950
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3
- rates (USD)
$2,000
- $3,500
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3
- rates (USD)
$1,750
- $3,950
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$899
- $1,950
/nt
- bedrooms 4
- community
- rental type Villa
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- sleeps 8
- baths 3
- rates (USD)
$1,695
- $3,350
/nt
- bedrooms 4
- community Wailea Beach Villas
- rental type Villa
- sleeps 8
- baths 3
- rates (USD)
$1,550
- $3,150
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$2,850
- $5,000
/nt
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,095
- $2,350
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$1,295
- $2,750
/nt
- bedrooms 3
- community
- rental type Villa
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- sleeps 6
- baths 3
- rates (USD)
$1,350
- $2,450
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$795
- $1,750
/nt
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$2,000
- $2,850
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$995
- $2,250
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$1,850
- $3,500
/nt
- bedrooms 4
- community
- rental type Villa
- sleeps 8
- baths 3
- rates (USD)
$995
- $2,400
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$1,350
- $2,950
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 4
- rates (USD)
$1,495
- $2,850
/nt
- bedrooms 4
- community
- rental type Villa
- sleeps 8
- baths 3
- rates (USD)
$1,595
- $3,150
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3
- rates (USD)
$1,295
- $2,350
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3
- rates (USD)
$1,350
- $2,050
/nt
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3
- rates (USD)
$1,195
- $2,450
/nt
- bedrooms 2
- community
- rental type Villa
- sleeps 4
- baths 2
- rates (USD)
$290
- $360
/nt
$2,050 - $2,550 /wk
- bedrooms 1
- community Ekahi Village
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,715
- $2,345
/wk
- bedrooms 4
- community Kihei Wailea Area
- rental type House
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- sleeps 10
- baths 5
- rates (USD)
$699
- $699
/nt
$4,893 - $4,893 /wk
$19,000 - $19,000 /mth
- bedrooms 0
- community Grand Champions
- rental type Studio
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- sleeps 2
- baths 1
- rates (USD)
$110
- $135
/nt
$95 - $120 /mth
- bedrooms 1
- community Wailea Ekahi Village
- rental type Condo
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- sleeps 3
- baths 1
- rates (USD)
$150
- $205
/nt
$800 - $1,400 /wk
$3,000 - $5,000 /mth
- bedrooms 4
- community
- rental type Villa
- sleeps 8
- baths 3
- rates (USD)
$1,450
- $3,250
/nt
- bedrooms 3
- community
- rental type Villa
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- sleeps 6
- baths 3½
- rates (USD)
$1,995
- $3,950
/nt
- bedrooms 1
- community Wailea Ekolu
- rental type Condo
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- sleeps 4
- baths 2
- rates (USD)
$200
- $325
/nt
$1,400 - $2,275 /wk
$5,000 - $6,000 /mth
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$1,995
- $3,500
/nt
- bedrooms 2
- community Wailea Ekahi Village
- rental type Condo
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- sleeps 6
- baths 2
- rates (USD)
$410
- $510
/nt
$2,870 - $3,570 /wk
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$235
- $310
/nt
$1,645 - $2,170 /wk
- bedrooms 1
- community Wailea Ekahi Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$250
- $350
/nt
$1,750 - $2,450 /wk
- bedrooms 3
- community Hoolei AOAO
- rental type Villa
- sleeps 8
- baths 3½
- rates (USD)
$595
- $1,400
/nt
$4,165 - $9,800 /wk
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$595
- $1,400
/nt
$4,165 - $9,800 /wk
- bedrooms 3
- community
- rental type Villa
- sleeps 6
- baths 3½
- rates (USD)
$595
- $1,400
/nt
$4,165 - $9,800 /wk
- bedrooms 3
- community Hoolei AOAO
- rental type Villa
- sleeps 8
- baths 3½
- rates (USD)
$595
- $1,400
/nt
$4,165 - $9,800 /wk
- bedrooms 3
- community Hoolei AOAO
- rental type Villa
- sleeps 8
- baths 3½
- rates (USD)
$595
- $1,400
/nt
$4,165 - $9,800 /wk
- bedrooms 3
- community Hoolei AOAO
- rental type Villa
- sleeps 8
- baths 3½
- rates (USD)
$595
- $1,400
/nt
$4,165 - $9,800 /wk
- bedrooms 2
- community Palms at Wailea
- rental type Condo
- sleeps 7
- baths 2
- rates (USD)
$1,200
- $2,350
/wk
- bedrooms 2
- community Palms at Wailea
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$2,650
- $2,950
/wk
- bedrooms 1
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$165
- $195
/nt
$1,155 - $1,365 /wk