Winter Timeshare Rentals in Hawaii

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,731 ($533/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

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Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$14,194 ($2,028/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,464 ($1,066/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 20–27, 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 20–27, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$8,036 ($1,148/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,674 ($953/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$5,748 ($821/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,128 ($875/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,508 ($1,358/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,001 ($1,000/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,464 ($1,066/night)

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Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

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The Point at Poipu

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,458 ($494/night)

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Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,358 ($765/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,292 ($899/night)

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The Point at Poipu

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,216 ($888/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,199 ($1,171/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$12,451 ($1,779/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 20–27, 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 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,522 ($1,217/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,873 ($1,125/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$15,285 ($1,092/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,892 ($985/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,091 ($1,156/night)

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Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$4,058 ($580/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,783 ($969/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$13,650 ($1,950/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 20–27, 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 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,783 ($969/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,202 ($743/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–23, 2026 (3 nights)
2 bed/3 bath, sleeps 8
$2,641 ($880/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$7,546 ($1,078/night)

Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,505 ($358/night)