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.
Hyatt Windward Pointe Resort
Key West, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
The Galleon Resort
Key West, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 6–10, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,330 ($332/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
The Galleon Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,058 ($580/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–17, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($278/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,711 ($673/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,423 ($808/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,930 ($704/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 5–9, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,914 ($416/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
Hyatt Beach House Resort
Key West, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)