Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 11–16, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($332/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,252 ($750/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,832 ($547/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,069 ($581/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 11–14, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,859 ($620/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,832 ($547/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $24,006 ($3,429/night)
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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
- $5,175 ($739/night)
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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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–18, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–18, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($440/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,731 ($390/night)
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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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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)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/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
- $5,206 ($744/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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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
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,946 ($707/night)
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
- $5,748 ($821/night)
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One Napili Way
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $2,423 ($346/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,848 ($407/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,930 ($990/night)
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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
- $6,320 ($903/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,368 ($338/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,306 ($472/night)
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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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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 12–15, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($808/night)
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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)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 9
- $5,257 ($1,314/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)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/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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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
- $10,924 ($1,561/night)
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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)
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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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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
- $5,595 ($799/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,886 ($412/night)
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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)