https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/The+Keys en Mon, 27 Jul 2026 05:22:04 -0700 3600

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 6–13, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,268 ($467/night)

]]> https://www.redweek.com/posting/R1499232 Fri, 17 Jul 2026 07:43:32 -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 13–17, 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 13–17, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,878 ($470/night)

]]> https://www.redweek.com/posting/R1486085 Mon, 22 Jun 2026 13:25:26 -0700 Verified & Protected

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 Tue, 26 May 2026 15:08:11 -0700 Verified & Protected

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 Tue, 26 May 2026 15:13:33 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1485736 Tue, 23 Jun 2026 10:49:14 -0700 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
• $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 20–27, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1481570 Mon, 08 Jun 2026 13:45:51 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,031 ($576/night)

]]> https://www.redweek.com/posting/R1490538 Mon, 06 Jul 2026 07:20:33 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,565 ($652/night)

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

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 20, 2026 – Jan 3, 2027 (14 nights)
• 2 bed/2 bath, sleeps 6
• $6,456 ($461/night)

]]> https://www.redweek.com/posting/R1490116 Fri, 03 Jul 2026 10:57:05 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 24–27, 2026 (3 nights)
• 2 bed/2.5 bath, sleeps 6
• $1,878 ($626/night)

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

The Galleon Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1483437 Fri, 19 Jun 2026 13:23:38 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,276 ($611/night)

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

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,167 ($595/night)

]]> https://www.redweek.com/posting/R1491173 Fri, 03 Jul 2026 09:44:02 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,167 ($595/night)

]]> https://www.redweek.com/posting/R1491095 Fri, 03 Jul 2026 09:44:06 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,374 ($625/night)

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

Hyatt Beach House 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/R1439177 Wed, 11 Mar 2026 11:43:46 -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 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 3–10, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1479225 Thu, 04 Jun 2026 06:40:18 -0700 Verified & Protected

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, 27 May 2026 07:39:26 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 3–10, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,984 ($712/night)

]]> https://www.redweek.com/posting/R1502116 Thu, 23 Jul 2026 14:08:04 -0700 Verified & Protected

The Banyan Resort

Key West, Florida

• Jan 9–16, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1480173 Mon, 15 Jun 2026 09:57:57 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jan 10–17, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,513 ($502/night)

]]> https://www.redweek.com/posting/R1488284 Fri, 26 Jun 2026 07:19:30 -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 Windward Pointe Resort

Key West, Florida

• Jan 10–17, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1485230 Mon, 22 Jun 2026 08:44:46 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Jan 16–23, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,513 ($502/night)

]]> https://www.redweek.com/posting/R1480170 Mon, 15 Jun 2026 09:40:48 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jan 17–21, 2027 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,764 ($441/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 17–24, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1482753 Mon, 15 Jun 2026 14:45:26 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 24–31, 2027 (7 nights)
• 2 bed/2.5 bath, sleeps 6
• $6,565 ($938/night)

]]> https://www.redweek.com/posting/R1478201 Wed, 03 Jun 2026 10:15:10 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 24–28, 2027 (4 nights)
• Studio/1 bath, sleeps 2
• $2,205 ($551/night)

]]> https://www.redweek.com/posting/R1480091 Wed, 10 Jun 2026 06:48:19 -0700

Hyatt Windward Pointe Resort

Key West, Florida

• Jan 30 – Feb 6, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1494660 Tue, 07 Jul 2026 13:47:35 -0700

Hyatt Beach House Resort

Key West, Florida

• Jan 31 – Feb 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1494038 Mon, 06 Jul 2026 12:19:41 -0700

Hyatt Beach House Resort

Key West, Florida

• Jan 31 – Feb 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,374 ($625/night)

]]> https://www.redweek.com/posting/R1502255 Thu, 23 Jul 2026 20:28:03 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jan 31 – Feb 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1474605 Wed, 20 May 2026 14:53:42 -0700

Hyatt Windward Pointe Resort

Key West, Florida

• Feb 6–13, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1494662 Tue, 07 Jul 2026 13:47:35 -0700

Hyatt Windward Pointe Resort

Key West, Florida

• Feb 7–14, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1503193 Sun, 26 Jul 2026 08:34:03 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Feb 7–14, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1483741 Sun, 14 Jun 2026 12:20:54 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Feb 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1496010 Wed, 15 Jul 2026 08:53:59 -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 14–20, 2027 (6 nights)
• 1 bed/1 bath, sleeps 4
• $3,622 ($604/night)

]]> https://www.redweek.com/posting/R1501132 Tue, 21 Jul 2026 13:51:03 -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 Windward Pointe Resort

Key West, Florida

• Feb 21 – Mar 6, 2027 (13 nights)
• 2 bed/2 bath, sleeps 6
• $6,543 ($503/night)

]]> https://www.redweek.com/posting/R1496004 Wed, 15 Jul 2026 09:21:03 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Feb 21–28, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,794 ($685/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