Vacation Rentals for Large Groups

Our tandem vacation rental listings can accommodate large groups of up to 32 guests! These listings offer all the space and sleeping capacity of renting a large home with all the added amenities and benefits of staying at an upscale resort. In addition, unlike many of the homes on Maui, these vacation rentals are all 100% legal for short term rentals. Listings combine 2, 3, and 4 neighboring residences and are typically located side-by-side, across the hall, or upstairs-downstairs.

153 properties
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Luxury Homes
Kaanapali Beachfront Estate
9 BR
10 BA
Sleeps 22
11076 Sq ft.
Oceanfront
$5,503 - $13,975Average nightly rate before taxes
New!
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Honua Kai Resort
Hokulani 601/5
5 BR
5.5 BA
Sleeps 14
3750 Sq ft.
Oceanfront Penthouse
Ka'anapali North Beach
$2,545 - $8,894Average nightly rate before taxes
New!
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Honua Kai Resort
Hokulani 601/5/6
7 BR
7.5 BA
Sleeps 20
4990 Sq ft.
Oceanfront Penthouse
Ka'anapali North Beach
$3,331 - $10,225Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Two 9A/C
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden
Ka'anapali North Beach
$1,389 - $5,399Average nightly rate before taxes
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Honua Kai Resort
Hokulani 814/5/8
4 BR
4 BA
Sleeps 14
2725 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,350 - $3,745Average nightly rate before taxes
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Honua Kai Resort
Konea 148/9
4 BR
4 BA
Sleeps 12
2710 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$1,157 - $3,043Average nightly rate before taxes
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Honua Kai Resort
Konea 406/7
3 BR
3 BA
Sleeps 14
2240 Sq ft.
Oceanview
Ka'anapali North Beach
$966 - $3,130Average nightly rate before taxes
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Honua Kai Resort
Hokulani 446/7
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Partial Oceanview
Ka'anapali North Beach
$912 - $3,159Average nightly rate before taxes
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Honua Kai Resort
Hokulani 248/50
5 BR
5 BA
Sleeps 14
3335 Sq ft.
Oceanfront
Ka'anapali North Beach
$1,205 - $4,637Average nightly rate before taxes
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The Kaanapali Alii
Kaanapali Alii 314/5
4 BR
4 BA
Sleeps 14
5188 Sq ft.
Oceanfront Ground Floor
Ka'anapali Beach
$1,643 - $6,457Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave One 2C/D
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden Elevated
Ka'anapali North Beach
$1,413 - $4,752Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave One 2A/B/C/D
12 BR
12 BA
Sleeps 32
8188 Sq ft.
Garden
Ka'anapali North Beach
$3,024 - $10,014Average nightly rate before taxes
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Honua Kai Resort
Hokulani 929/33/37
6 BR
6 BA
Sleeps 18
3480 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,897 - $5,067Average nightly rate before taxes
New!
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The Kaanapali Alii
Kaanapali Alii 312/3/4/5
7 BR
8 BA
Sleeps 24
6405 Sq ft.
Oceanview Ground Floor
Ka'anapali Beach
$3,198 - $9,823Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Three 16B/C/D
9 BR
9 BA
Sleeps 24
6141 Sq ft.
Garden
Ka'anapali North Beach
$2,219 - $7,965Average nightly rate before taxes
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Honua Kai Resort
Hokulani 403/4
6 BR
6 BA
Sleeps 18
3880 Sq ft.
Premier Oceanview
Ka'anapali North Beach
$1,749 - $6,603Average nightly rate before taxes
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Honua Kai Resort
Hokulani 728/29/30/32
6 BR
6 BA
Sleeps 20
3605 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,797 - $4,734Average nightly rate before taxes
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Honua Kai Resort
Hokulani 402/3/4/5
11 BR
11 BA
Sleeps 32
7205 Sq ft.
Oceanfront
Ka'anapali North Beach
$4,189 - $11,571Average nightly rate before taxes
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Honua Kai Resort
Hokulani 549/51
5 BR
5 BA
Sleeps 15
3365 Sq ft.
Oceanfront
Ka'anapali North Beach
$1,624 - $6,399Average nightly rate before taxes
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Honua Kai Resort
Konea 302/3
5 BR
5 BA
Sleeps 14
3530 Sq ft.
Oceanfront
Ka'anapali North Beach
$1,654 - $5,249Average nightly rate before taxes
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Honua Kai Resort
Hokulani 814/5/6/8/20
7 BR
7 BA
Sleeps 24
4780 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$2,389 - $4,680Average nightly rate before taxes
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Honua Kai Resort
Konea 613/4/5
4 BR
4 BA
Sleeps 14
2610 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,143 - $3,402Average nightly rate before taxes
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Honua Kai Resort
Hokulani 105/9/11
6 BR
6 BA
Sleeps 18
3500 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$1,632 - $5,586Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave One 4A/B
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden Grounded
Ka'anapali North Beach
$1,481 - $5,256Average nightly rate before taxes