Winter Rentals
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/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
- $5,420 ($774/night)
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
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 Sunset Harbor Resort
Key West, Florida- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,557 ($794/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)
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)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
Verified & Protected
The Galleon Resort
Key West, Florida- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/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 13–20, 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)
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 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
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 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 Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,166 ($595/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)