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.

152 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 601/5/6
7 BR
7.5 BA
Sleeps 20
4990 Sq ft.
Oceanfront Penthouse
Ka'anapali North Beach
$3,264 - $10,376Average 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
$2,486 - $8,894Average nightly rate before taxes
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The Kaanapali Alii
Kaanapali Alii 495/496
4 BR
4 BA
Sleeps 15
3614 Sq ft.
Premier Oceanview
Ka'anapali Beach
$1,133 - $4,267Average nightly rate before taxes
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Honua Kai Resort
Hokulani 109/11
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$982 - $3,792Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Two 10C/D
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden Elevated
Ka'anapali North Beach
$1,329 - $5,529Average nightly rate before taxes
Hokulani 246
Hokulani 246
Hokulani 246
Honua Kai Resort
Hokulani 246/8
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Partial Oceanview
Ka'anapali North Beach
$837 - $2,962Average 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
$1,393 - $5,228Average nightly rate before taxes
New!
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The Kaanapali Alii
Kaanapali Alii 313/4/5
5 BR
6 BA
Sleeps 18
4860 Sq ft.
Oceanview Ground Floor
Ka'anapali Beach
$2,173 - $8,019Average nightly rate before taxes
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Honua Kai Resort
Hokulani 250/51
6 BR
6 BA
Sleeps 16
4470 Sq ft.
Oceanfront
Ka'anapali North Beach
$2,005 - $5,521Average nightly rate before taxes
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Honua Kai Resort
Konea 625/9
6 BR
6 BA
Sleeps 16
3220 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,557 - $5,674Average nightly rate before taxes
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Honua Kai Resort
Hokulani 105/9
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$1,098 - $3,792Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Three 16A/B/C/D
12 BR
12 BA
Sleeps 32
8188 Sq ft.
Garden
Ka'anapali North Beach
$3,021 - $10,777Average nightly rate before taxes
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Honua Kai Resort
Hokulani 403/5
5 BR
5 BA
Sleeps 16
3040 Sq ft.
Oceanview
Ka'anapali North Beach
$1,402 - $4,637Average nightly rate before taxes
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Honua Kai Resort
Konea 350/1
6 BR
6 BA
Sleeps 16
4510 Sq ft.
Oceanfront
Ka'anapali North Beach
$2,479 - $7,884Average nightly rate before taxes
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Honua Kai Resort
Hokulani 446/8
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Partial Oceanview
Ka'anapali North Beach
$843 - $2,858Average nightly rate before taxes
Hokulani 511
Hokulani 511
Hokulani 511
Honua Kai Resort
Hokulani 510/1
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Oceanview
Ka'anapali North Beach
$935 - $3,383Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Two 9A/B
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden Grounded
Ka'anapali North Beach
$1,297 - $5,656Average 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
Hokulani 447/8
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Partial Oceanview
Ka'anapali North Beach
$912 - $3,025Average nightly rate before taxes
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The Kaanapali Alii
Kaanapali Alii 272/4
4 BR
4 BA
Sleeps 12
3000 Sq ft.
Partial Oceanview
Ka'anapali Beach
$931 - $3,523Average nightly rate before taxes
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Honua Kai Resort
Konea 401/2
5 BR
5 BA
Sleeps 14
3850 Sq ft.
Oceanfront
Ka'anapali North Beach
$2,007 - $6,023Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Two 8A/D
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden
Ka'anapali North Beach
$1,470 - $5,810Average nightly rate before taxes
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The Kaanapali Alii
Kaanapali Alii A312/4
4 BR
4 BA
Sleeps 14
3350 Sq ft.
Garden Ground Floor
Ka'anapali Beach
$1,436 - $4,879Average nightly rate before taxes