Winter Timeshare Rentals in Hawaii

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Sheraton Kauai Resort Villas

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,110 ($1,016/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

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 12–19, 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 North

Lahaina, Hawaii

Dec 12–19, 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

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,475 ($782/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
$3,344 ($478/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
$3,399 ($486/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
$4,053 ($579/night)

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Pono Kai

Kapaa, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,660 ($237/night)

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Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,835 ($548/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
$3,054 ($436/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,658 ($665/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,886 ($412/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,813 ($545/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,494 ($642/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)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,366 ($767/night)

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The Point at Poipu

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

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

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,977 ($711/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,731 ($533/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

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,358 ($765/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
$11,466 ($1,638/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,202 ($743/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

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

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Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,150 ($307/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
$5,475 ($782/night)

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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 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

Lahaina, Hawaii

Dec 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$2,450 ($490/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,058 ($580/night)

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Hanalei Bay Resort

Princeville, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,314 ($331/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

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,276 ($611/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
$5,966 ($852/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)

Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,276 ($611/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,012 ($287/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 - 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

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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,531 ($362/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 Waiohai Beach Club

Koloa, Hawaii

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