Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida
  • May 4–11, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,696 ($385/night)

The Galleon Resort

Key West, Florida
  • Jul 4–11, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($549/night)

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
  • Jul 18–25, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,022 ($432/night)
Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida
  • May 21–25, 2026 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,878 ($470/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)

Hyatt Windward Pointe Resort

Key West, Florida
  • May 31 – Jun 6, 2026 (6 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,313 ($385/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • May 23–30, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,222 ($603/night)

The Galleon Resort

Key West, Florida
  • Jul 25 – Aug 1, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,385 ($626/night)

Hyatt Beach House Resort

Key West, Florida
  • Mar 28 – Apr 4, 2027 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($471/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 17–24, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($549/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 10–17, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($549/night)

The Galleon Resort

Key West, Florida
  • Dec 12–19, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,930 ($704/night)

The Galleon Resort

Key West, Florida
  • Dec 5–12, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,930 ($704/night)

The Galleon Resort

Key West, Florida
  • Nov 28 – Dec 5, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,930 ($704/night)
Verified & Protected

Hyatt Beach House Resort

Key West, Florida
  • Jun 7–14, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,535 ($505/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)

Hyatt Windward Pointe Resort

Key West, Florida
  • Mar 9–13, 2027 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,769 ($442/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Jul 25 – Aug 1, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $5,366 ($767/night)
Verified & Protected

Hyatt Beach House Resort

Key West, Florida
  • May 19–22, 2026 (3 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,165 ($388/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • May 17–24, 2026 (7 nights)
  • 2 bed/2.5 bath, sleeps 6
  • $3,513 ($502/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Jun 14–18, 2026 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,878 ($470/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Feb 21–28, 2027 (7 nights)
  • 1 bed/1 bath, sleeps 4
  • $3,622 ($517/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Aug 1–8, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,949 ($564/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 Beach House Resort

Key West, Florida
  • Jun 14–21, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($471/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Oct 4–11, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,859 ($408/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Jul 11–18, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,458 ($494/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Jun 27 – Jul 4, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,568 ($510/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Oct 24–31, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,658 ($665/night)

Hyatt Beach House Resort

Key West, Florida
  • Oct 20–24, 2026 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,205 ($551/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Jul 3–6, 2026 (3 nights)
  • 1 bed/1 bath, sleeps 4
  • $1,660 ($553/night)

Hyatt Sunset Harbor Resort

Key West, Florida
  • Oct 18–25, 2026 (7 nights)
  • 2 bed/2.5 bath, sleeps 6
  • $4,603 ($658/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Aug 15–22, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,696 ($385/night)

Hyatt Beach House Resort

Key West, Florida
  • Jul 19–26, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,077 ($440/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Aug 8–15, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,532 ($362/night)
Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida
  • May 3–7, 2026 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,220 ($305/night)
Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida
  • May 3–7, 2026 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,220 ($305/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • May 16–23, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,058 ($580/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • May 16–23, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $4,058 ($580/night)
Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida
  • Jul 12–16, 2026 (4 nights)
  • 1 bed/1 bath, sleeps 4
  • $1,747 ($437/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)
Verified & Protected

Hyatt Beach House Resort

Key West, Florida
  • Jun 2–9, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,404 ($486/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
  • Dec 26, 2026 – Jan 2, 2027 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $5,039 ($720/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Oct 24–31, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $6,565 ($938/night)

Hyatt Windward Pointe Resort

Key West, Florida
  • Oct 17–24, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,077 ($440/night)
Verified & Protected

The Galleon Resort

Key West, Florida
  • Oct 10–17, 2026 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,513 ($502/night)