https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/Key+West en Tue, 26 May 2026 03:21:29 -0700 3600 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,058 ($580/night)

]]> https://www.redweek.com/posting/R1454718 Mon, 13 Apr 2026 11:56:15 -0700 Verified & Protected

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 Fri, 01 May 2026 08:25:52 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,984 ($712/night)

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

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,167 ($595/night)

]]> https://www.redweek.com/posting/R1472362 Wed, 13 May 2026 17:01:26 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,167 ($595/night)

]]> https://www.redweek.com/posting/R1472361 Wed, 13 May 2026 17:01:26 -0700 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 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 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1471074 Tue, 12 May 2026 11:51:00 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1471453 Tue, 12 May 2026 12:48:33 -0700 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
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1449977 Tue, 07 Apr 2026 09:28:40 -0700 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 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

• Dec 27, 2026 – Jan 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,276 ($611/night)

]]> https://www.redweek.com/posting/R1474091 Thu, 21 May 2026 08:07:15 -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

The Galleon Resort

Key West, Florida

• Jan 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $7,464 ($1,066/night)

]]> https://www.redweek.com/posting/R1471666 Tue, 12 May 2026 13:36:57 -0700

Hyatt Beach House Resort

Key West, Florida

• Jan 3–10, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1472363 Wed, 13 May 2026 17:01:26 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 10–17, 2027 (7 nights)
• 2 bed/2.5 bath, sleeps 6
• $5,693 ($813/night)

]]> https://www.redweek.com/posting/R1469704 Thu, 07 May 2026 12:45:55 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 17–24, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,995 ($714/night)

]]> https://www.redweek.com/posting/R1469533 Wed, 06 May 2026 12:03:05 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jan 17–21, 2027 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,834 ($459/night)

]]> https://www.redweek.com/posting/R1464924 Wed, 29 Apr 2026 14:00:38 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jan 24–31, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,185 ($455/night)

]]> https://www.redweek.com/posting/R1467014 Mon, 04 May 2026 12:03:24 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jan 31 – Feb 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,031 ($576/night)

]]> https://www.redweek.com/posting/R1474605 Wed, 20 May 2026 14:53:42 -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 Verified & Protected

The Galleon Resort

Key West, Florida

• Feb 20–27, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,636 ($377/night)

]]> https://www.redweek.com/posting/R1472987 Mon, 18 May 2026 06:35:39 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Feb 21–28, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1472064 Fri, 15 May 2026 09:13:45 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Feb 27 – Mar 6, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,636 ($377/night)

]]> https://www.redweek.com/posting/R1472989 Mon, 18 May 2026 06:35:25 -0700 Verified & Protected

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, 10 Apr 2026 08:01:37 -0700