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 Sunset Harbor Resort
Key West, Florida- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/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 13–17, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/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 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,565 ($652/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($461/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,878 ($626/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,458 ($494/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,374 ($625/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/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
The Galleon Resort
Key West, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,464 ($1,066/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
The Banyan Resort
Key West, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $5,693 ($813/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Coconut Beach Resort
Key West, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,764 ($441/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $6,565 ($938/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($551/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,374 ($625/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,802 ($543/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/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 14–20, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 21 – Mar 6, 2027 (13 nights)
- 2 bed/2 bath, sleeps 6
- $6,543 ($503/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)