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

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

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 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
$3,295 ($471/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
$3,840 ($549/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

Lahaina, Hawaii

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

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)
2 bed/2 bath, sleeps 8
$8,745 ($1,249/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
$3,457 ($494/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)
1 bed/1 bath, sleeps 4
$3,350 ($478/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)

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
$4,385 ($626/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
$6,456 ($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
$3,840 ($549/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)
2 bed/2 bath, sleeps 6
$5,366 ($767/night)

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

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

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

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 - 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

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 - 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

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

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 Nanea Ocean Villas

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/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
$16,033 ($1,145/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)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 9–20, 2026 (11 nights)
2 bed/2 bath, sleeps 8
$10,816 ($983/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 10–18, 2026 (8 nights)
3 bed/2 bath, sleeps 8
$10,870 ($1,359/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$3,832 ($547/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,478 ($354/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 11–18, 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

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,494 ($642/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,676 ($525/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,456 ($922/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$10,924 ($1,561/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,560 ($937/night)

Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,938 ($848/night)