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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Maui Beach Vacation Club
Kihei, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,650 ($236/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,793 ($828/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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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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Maui Schooner
Kihei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,161 ($309/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)
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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
- $14,195 ($2,028/night)
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Maui Beach Vacation Club
Kihei, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($255/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)
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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)
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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)
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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)
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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
- $4,794 ($685/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
- $4,984 ($712/night)
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WorldMark Kihei Resort
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($276/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
- $5,202 ($743/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
- $10,371 ($1,482/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,546 ($1,078/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $16,368 ($2,338/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,110 ($1,016/night)
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Maui Lea at Maui Hill
Kihei, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,421 ($346/night)
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WorldMark Kihei Resort
Kihei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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WorldMark Kihei Resort
Kihei, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
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Maui Schooner
Kihei, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)