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
Image 1
Image 2
Image 3
Luxury Homes
Kaanapali Beachfront Estate
9 BR
10 BA
Sleeps 22
11076 Sq ft.
Oceanfront
$5,503 - $13,975Average nightly rate before taxes
New!
Image 1
Image 2
Image 3
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
New!
Image 1
Image 2
Image 3
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 - $10,376Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Konea 725/9
6 BR
6 BA
Sleeps 16
3220 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,757 - $6,066Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Hokulani 402/3
6 BR
6 BA
Sleeps 18
4270 Sq ft.
Oceanfront
Ka'anapali North Beach
$2,503 - $8,059Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Konea 330/31/32
4 BR
4 BA
Sleeps 14
2275 Sq ft.
Oceanview
Ka'anapali North Beach
$852 - $3,239Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Konea 402/4/6
6 BR
6 BA
Sleeps 20
4425 Sq ft.
Oceanfront
Ka'anapali North Beach
$1,754 - $6,005Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Hokulani 510/12
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Partial Oceanview
Ka'anapali North Beach
$783 - $3,177Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Konea 645/9
5 BR
5 BA
Sleeps 14
3245 Sq ft.
Premier Oceanview
Ka'anapali North Beach
$1,336 - $4,287Average nightly rate before taxes
Image 1
Image 2
Image 3
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
Image 1
Image 2
Image 3
The Kaanapali Alii
Kaanapali Alii 314/5
4 BR
4 BA
Sleeps 14
5188 Sq ft.
Oceanfront Ground Floor
Ka'anapali Beach
$1,674 - $6,457Average nightly rate before taxes
Image 1
Image 2
Image 3
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
Image 1
Image 2
Image 3
Honua Kai Resort
Konea 613/4/5
4 BR
4 BA
Sleeps 14
2610 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,134 - $3,402Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Hokulani 814/5/6/8
5 BR
5 BA
Sleeps 18
3540 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,710 - $4,558Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Konea 210/12/14
4 BR
3 BA
Sleeps 14
2335 Sq ft.
Mountainview
Ka'anapali North Beach
$972 - $2,627Average 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
Image 1
Image 2
Image 3
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
Image 1
Image 2
Image 3
Honua Kai Resort
Konea K729/37
4 BR
4 BA
Sleeps 12
2180 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$1,082 - $4,144Average nightly rate before taxes
Image 1
Image 2
Image 3
The Kaanapali Alii
Kaanapali Alii 241/42
4 BR
4 BA
Sleeps 12
3088 Sq ft.
Oceanview
Ka'anapali Beach
$966 - $3,666Average nightly rate before taxes
Image 1
Image 2
Image 3
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
Image 1
Image 2
Image 3
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
Image 1
Image 2
Image 3
Honua Kai Resort
Hokulani 402/4/5
8 BR
8 BA
Sleeps 22
5265 Sq ft.
Oceanfront
Ka'anapali North Beach
$2,960 - $8,517Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Hokulani 929/30/33/37
7 BR
7 BA
Sleeps 22
4245 Sq ft.
Deluxe Oceanview
Ka'anapali North Beach
$2,217 - $5,809Average nightly rate before taxes
Image 1
Image 2
Image 3
Honua Kai Resort
Hokulani 105/47
4 BR
4 BA
Sleeps 12
2200 Sq ft.
Garden Ground Floor
Ka'anapali North Beach
$1,068 - $3,589Average nightly rate before taxes