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.

149 properties
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Luxury Homes
Kaanapali Beachfront Estate
9 BR
10 BA
Sleeps 22
11076 Sq ft.
Oceanfront
$5,250 - $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
$2,332 - $8,894Average nightly rate before taxes
New!
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Honua Kai Resort
Hokulani 605/6
4 BR
4 BA
Sleeps 12
2340 Sq ft.
Oceanview Penthouse
Ka'anapali North Beach
$976 - $3,460Average 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
New!
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Honua Kai Resort
Konea 109/10/13
5 BR
5 BA
Sleeps 16
3370 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$1,173 - $4,154Average nightly rate before taxes
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Honua Kai Resort
Konea 143/4/5
5 BR
5 BA
Sleeps 16
3395 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$1,268 - $3,978Average 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
$1,094 - $4,267Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave One 2B/D
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden
Ka'anapali North Beach
$1,352 - $5,810Average nightly rate before taxes
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The Kaanapali Alii
Kaanapali Alii 241/42
4 BR
4 BA
Sleeps 12
3088 Sq ft.
Oceanview
Ka'anapali Beach
$960 - $3,666Average 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
$1,486 - $5,249Average nightly rate before taxes
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The Kaanapali Alii
Kaanapali Alii 312/4/5
6 BR
6 BA
Sleeps 20
5188 Sq ft.
Oceanfront Ground Floor
Ka'anapali Beach
$2,483 - $8,268Average nightly rate before taxes
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Honua Kai Resort
Hokulani 649/50
5 BR
6 BA
Sleeps 14
3750 Sq ft.
Oceanfront Penthouse
Ka'anapali North Beach
$2,558 - $7,236Average nightly rate before taxes
New!
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Luana Garden Villas at Honua Kai
Enclave Three 17A/17D/18B
9 BR
9 BA
Sleeps 24
6141 Sq ft.
Garden
Ka'anapali North Beach
$2,006 - $8,855Average nightly rate before taxes
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Honua Kai Resort
Konea 407/8
4 BR
3 BA
Sleeps 14
2245 Sq ft.
Oceanview
Ka'anapali North Beach
$843 - $3,112Average 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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Honua Kai Resort
Konea 645/9
5 BR
5 BA
Sleeps 14
3245 Sq ft.
Premier Oceanview
Ka'anapali North Beach
$1,301 - $4,287Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Three 16A/C/D
9 BR
9 BA
Sleeps 24
6141 Sq ft.
Garden
Ka'anapali North Beach
$2,061 - $7,949Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Two 7C/D
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden Elevated
Ka'anapali North Beach
$1,317 - $5,529Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Three 16A/C
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden
Ka'anapali North Beach
$1,382 - $5,388Average 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
$2,703 - $9,943Average 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 - $6,850Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave Three 15A/C
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Garden
Ka'anapali North Beach
$1,333 - $5,159Average nightly rate before taxes
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Honua Kai Resort
Konea 402/4
5 BR
5 BA
Sleeps 14
3530 Sq ft.
Oceanfront
Ka'anapali North Beach
$1,433 - $5,530Average nightly rate before taxes
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Luana Garden Villas at Honua Kai
Enclave One 6A/C
6 BR
6 BA
Sleeps 16
4094 Sq ft.
Partial Oceanview
Ka'anapali North Beach
$1,468 - $5,015Average nightly rate before taxes