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.
Pono Kai
Kapaa, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,769 ($253/night)
Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,588 ($227/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,780 ($254/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,780 ($254/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($166/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($166/night)
Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($439/night)
Pono Kai
Kapaa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,390 ($341/night)
Pono Kai
Kapaa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Pono Kai
Kapaa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Pono Kai
Kapaa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Pono Kai
Kapaa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,932 ($276/night)
WorldMark Kapaa Shore
Kapaa, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,543 ($363/night)