Winter Rentals
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,725 ($431/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
The Galleon Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,150 ($307/night)
Coconut Mallory Marina & Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($354/night)
Verified & Protected
The Banyan Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($253/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,095 ($299/night)
Verified & Protected
The Banyan Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 21–27, 2025 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,495 ($249/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 21–25, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $832 ($208/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,330 ($619/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 23–27, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,714 ($429/night)
The Galleon Resort
Key West, Florida- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,562 ($1,366/night)
Verified & Protected
The Banyan Resort
Key West, Florida- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,840 ($549/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,347 ($907/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
The Galleon Resort
Key West, Florida- Jan 3–10, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($276/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hyatt Beach House Resort
Key West, Florida- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 4–10, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,204 ($367/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,440 ($360/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,347 ($907/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($315/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 18–24, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($495/night)
Hyatt Beach House Resort
Key West, Florida- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,039 ($434/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,238 ($891/night)
The Galleon Resort
Key West, Florida- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($354/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,693 ($813/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,240 ($463/night)