Winter Timeshare Rentals in Hawaii

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Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$8,410 ($1,201/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,949 ($564/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,976 ($854/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,987 ($1,284/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,374 ($625/night)

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Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$6,227 ($890/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

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Sheraton Kauai Resort Villas

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,546 ($1,078/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,748 ($821/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,976 ($854/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$21,825 ($3,118/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$12,233 ($1,748/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,266 ($895/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,840 ($549/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$2,859 ($715/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,346 ($907/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,707 ($1,530/night)

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Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,564 ($938/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,830 ($1,404/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,222 ($889/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,644 ($1,092/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,775 ($825/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,240 ($463/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,455 ($922/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

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Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,647 ($1,092/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,712 ($673/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,920 ($1,560/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,380 ($1,483/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,726 ($1,389/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,690 ($1,242/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,455 ($922/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$10,867 ($1,552/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,977 ($711/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$10,925 ($1,561/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,455 ($922/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$3,949 ($987/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,505 ($358/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,265 ($609/night)