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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,636 ($1,234/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,038 ($720/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,105 ($1,015/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,512 ($502/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $14,195 ($2,028/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,963 ($1,280/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,650 ($1,950/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,854 ($1,265/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,750 ($393/night)
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Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,440 ($634/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,802 ($829/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,786 ($541/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,721 ($532/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,038 ($720/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,943 ($1,420/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,091 ($1,156/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,583 ($798/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,545 ($1,078/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,495 ($1,071/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,545 ($1,078/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,766 ($681/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($822/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,636 ($662/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,494 ($642/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,704 ($529/night)
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Wyndham Vacation Resorts Royal Garden at Waikiki
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,095 ($299/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,948 ($564/night)
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Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,516 ($1,502/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,870 ($1,553/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($822/night)
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Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,786 ($541/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($822/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,631 ($1,233/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,502 ($1,072/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,803 ($1,543/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,404/night)