Winter Timeshare Rentals in Lahaina

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 1–8, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,911 ($844/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 3–10, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,382 ($483/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 3–10, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,451 ($493/night)

Verified & Protected

Kahana Falls

Lahaina, Hawaii

Dec 3–10, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,096 ($299/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 4–11, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,888 ($984/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,658 ($665/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,022 ($432/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 4–11, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 5–11, 2026 (6 nights)
2 bed/3 bath, sleeps 8
$5,039 ($840/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,167 ($595/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,069 ($438/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,456 ($922/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,073 ($439/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,350 ($478/night)

Verified & Protected

One Napili Way

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 6
$2,423 ($346/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,107 ($872/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,423 ($346/night)

Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,800 ($829/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$8,636 ($1,234/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,622 ($517/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,560 ($937/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)

Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,969 ($853/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$3,949 ($564/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$4,112 ($588/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,290 ($470/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,949 ($564/night)

Kahana Beach Resort

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,022 ($432/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 7–21, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$15,728 ($1,123/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,712 ($673/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 9–16, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$9,246 ($1,321/night)