Winter Timeshare Rentals in Kaanapali

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,740 ($820/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,745 ($1,249/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$12,042 ($1,720/night)

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/2 bath, sleeps 8
$3,153 ($450/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,380 ($1,483/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$5,038 ($720/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$6,091 ($870/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$9,830 ($1,404/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$8,410 ($1,201/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,535 ($1,076/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,546 ($1,078/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,784 ($1,398/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$10,707 ($1,530/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,732 ($819/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,938 ($848/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$8,418 ($1,203/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,705 ($1,529/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$9,173 ($1,310/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$10,623 ($1,518/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$9,944 ($1,421/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$9,028 ($1,290/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$11,256 ($1,608/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$9,778 ($1,397/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$8,502 ($1,215/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,042 ($1,435/night)

Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$6,884 ($983/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$10,053 ($1,436/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,036 ($1,148/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$4,984 ($712/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$6,892 ($985/night)

Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$8,800 ($1,257/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$5,802 ($829/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$17,192 ($2,456/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$8,693 ($1,242/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$12,660 ($1,809/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,320 ($903/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$7,274 ($1,039/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,785 ($1,112/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$5,557 ($794/night)