https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/Key+West?sort=date en Sun, 05 Apr 2026 16:49:02 -0700 3600

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1454718 Tue, 31 Mar 2026 10:42:30 -0700

The Galleon Resort

Key West, Florida

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

]]> https://www.redweek.com/posting/R1452921 Fri, 27 Mar 2026 09:09:37 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 6–10, 2026 (4 nights)
• Studio/1 bath, sleeps 2
• $1,330 ($332/night)

]]> https://www.redweek.com/posting/R1417666 Wed, 14 Jan 2026 09:15:40 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1320358 Sat, 09 Aug 2025 10:15:20 -0700

The Galleon Resort

Key West, Florida

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

]]> https://www.redweek.com/posting/R1452927 Fri, 27 Mar 2026 09:13:22 -0700 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)

]]> https://www.redweek.com/posting/R1406723 Mon, 05 Jan 2026 12:01:36 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 13–17, 2026 (4 nights)
• Studio/1 bath, sleeps 2
• $1,110 ($278/night)

]]> https://www.redweek.com/posting/R1407731 Mon, 05 Jan 2026 13:47:19 -0800 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)

]]> https://www.redweek.com/posting/R1443552 Mon, 30 Mar 2026 13:26:10 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1415598 Tue, 20 Jan 2026 14:57:04 -0800 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)

]]> https://www.redweek.com/posting/R1408372 Wed, 31 Dec 2025 10:02:24 -0800 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)

]]> https://www.redweek.com/posting/R1407911 Mon, 05 Jan 2026 14:03:54 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 24–27, 2026 (3 nights)
• 2 bed/2.5 bath, sleeps 6
• $2,423 ($808/night)

]]> https://www.redweek.com/posting/R1427811 Wed, 25 Feb 2026 15:03:27 -0800 Verified & Protected

Coconut Mallory Marina & Resort

Key West, Florida

• Dec 25, 2026 – Jan 1, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1429301 Wed, 04 Mar 2026 12:39:30 -0800 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)

]]> https://www.redweek.com/posting/R1439178 Wed, 11 Mar 2026 11:18:47 -0700

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)

]]> https://www.redweek.com/posting/R1449977 Sun, 22 Mar 2026 14:48:25 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 27, 2026 – Jan 3, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1417678 Wed, 14 Jan 2026 09:25:54 -0800 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)

]]> https://www.redweek.com/posting/R1439177 Wed, 11 Mar 2026 11:43:46 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jan 5–9, 2027 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,824 ($456/night)

]]> https://www.redweek.com/posting/R1416356 Fri, 30 Jan 2026 15:15:55 -0800 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)

]]> https://www.redweek.com/posting/R1441151 Thu, 26 Mar 2026 09:28:22 -0700 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)

]]> https://www.redweek.com/posting/R1435934 Wed, 11 Mar 2026 11:55:52 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Feb 21–28, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,622 ($517/night)

]]> https://www.redweek.com/posting/R1450570 Mon, 23 Mar 2026 20:34:40 -0700

Hyatt Beach House Resort

Key West, Florida

• Feb 28 – Mar 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1456418 Fri, 03 Apr 2026 14:45:58 -0700