Winter Rentals
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hyatt Beach House Resort
Key West, Florida- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 19–22, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($717/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $5,366 ($767/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
- $4,876 ($696/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 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)
- 1 bed/1 bath, sleeps 4
- $1,440 ($360/night)
Hyatt Beach House Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/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)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–24, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,330 ($332/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 Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,111 ($587/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jan 5–9, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)