Winter Timeshare Rentals in Lahaina

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
$6,560 ($937/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$9,176 ($1,311/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

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,421 ($346/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,268 ($467/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
$3,350 ($478/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,124 ($875/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,748 ($821/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
$3,486 ($498/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,186 ($455/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)

Verified & Protected

One Napili Way

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
3 bed/2 bath, sleeps 6
$2,423 ($346/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,240 ($463/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,731 ($533/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,641 ($377/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,025 ($575/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,478 ($354/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 13–18, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$3,622 ($724/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$2,532 ($506/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–18, 2026 (5 nights)
2 bed/3 bath, sleeps 8
$4,711 ($942/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,429 ($918/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,467 ($352/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,458 ($494/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,309 ($1,187/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,595 ($656/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,993 ($856/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,712 ($673/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,422 ($346/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,859 ($408/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,801 ($829/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–20, 2026 (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 15–22, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,468 ($495/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 16–21, 2026 (5 nights)
2 bed/3 bath, sleeps 8
$3,568 ($714/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 17–27, 2026 (10 nights)
1 bed/2 bath, sleeps 4
$7,928 ($793/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (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 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$9,181 ($1,312/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,707 ($1,530/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,894 ($556/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,582 ($1,226/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$7,541 ($1,077/night)