Winter Timeshare Rentals in Hawaii

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 14–18, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$10,925 ($2,731/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,556 ($937/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–28, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$14,195 ($1,092/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,564 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,358 ($908/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/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 Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 16–23, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$7,437 ($1,062/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)

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Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

Dec 16–27, 2026 (11 nights)
2 bed/2 bath, sleeps 6
$5,366 ($488/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 16–23, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,513 ($502/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 16–23, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$8,413 ($1,202/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 16–23, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,497 ($500/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

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Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 16–23, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$1,660 ($237/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 17–22, 2026 (5 nights)
Studio/1 bath, sleeps 2
$2,147 ($429/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 17–24, 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 17–27, 2026 (10 nights)
1 bed/2 bath, sleeps 4
$7,928 ($793/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
$5,039 ($720/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
$7,274 ($1,039/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
$8,745 ($1,249/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,047 ($292/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
$6,946 ($992/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,887 ($984/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,949 ($564/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)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 18–23, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$4,325 ($865/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
$4,821 ($689/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,470 ($781/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
$8,036 ($1,148/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
$5,361 ($766/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,801 ($829/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 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 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$4,493 ($642/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,023 ($718/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$12,004 ($1,715/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,464 ($1,066/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
$4,162 ($595/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
$8,740 ($1,249/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$13,050 ($1,864/night)

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Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$12,233 ($1,748/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–28, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$8,199 ($820/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
$6,560 ($937/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
$7,274 ($1,039/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

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