https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/The+Keys en Fri, 18 Sep 2026 05:13:30 -0700 3600 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,268 ($467/night)

]]> https://www.redweek.com/posting/R1516891 Tue, 08 Sep 2026 13:22:23 -0700 Verified & Protected

The Banyan Resort

Key West, Florida

• Dec 12–19, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1515378 Tue, 08 Sep 2026 09:58:03 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,748 ($821/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 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1472361 Tue, 26 May 2026 15:08:11 -0700 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

Coconut Mallory Marina & Resort

Key West, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1517107 Wed, 26 Aug 2026 09:18:24 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1504979 Wed, 29 Jul 2026 15:36:43 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,595 ($656/night)

]]> https://www.redweek.com/posting/R1520124 Tue, 01 Sep 2026 17:58:49 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1523329 Thu, 10 Sep 2026 10:23:31 -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/R1522640 Tue, 08 Sep 2026 07:58:38 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,214 ($602/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)
• Studio/1 bath, sleeps 2
• $3,840 ($549/night)

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

Hyatt Sunset Harbor Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,298 ($614/night)

]]> https://www.redweek.com/posting/R1526830 Thu, 17 Sep 2026 14:21:57 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1518505 Mon, 31 Aug 2026 11:28:15 -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
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1520225 Thu, 03 Sep 2026 09:09:57 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1523574 Wed, 09 Sep 2026 17:26:07 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 20–26, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $2,968 ($495/night)

]]> https://www.redweek.com/posting/R1507545 Thu, 06 Aug 2026 13:55:10 -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

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

The Banyan Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/1 bath, sleeps 6
• $5,175 ($739/night)

]]> https://www.redweek.com/posting/R1509050 Fri, 14 Aug 2026 09:01:40 -0700 Verified & Protected

The Banyan Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $3,497 ($500/night)

]]> https://www.redweek.com/posting/R1509049 Fri, 14 Aug 2026 09:01:24 -0700 Verified & Protected

Coconut Mallory Marina & Resort

Key West, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,886 ($412/night)

]]> https://www.redweek.com/posting/R1509300 Fri, 14 Aug 2026 11:06:08 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Dec 27, 2026 – Jan 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,031 ($576/night)

]]> https://www.redweek.com/posting/R1519636 Wed, 02 Sep 2026 11:22:37 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Dec 27, 2026 – Jan 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1512031 Fri, 21 Aug 2026 11:01:34 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Dec 31, 2026 – Jan 3, 2027 (3 nights)
• 2 bed/2 bath, sleeps 6
• $1,748 ($583/night)

]]> https://www.redweek.com/posting/R1522231 Tue, 08 Sep 2026 14:10:56 -0700 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 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 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 3–10, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1502116 Wed, 29 Jul 2026 12:18:59 -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 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

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 Beach House Resort

Key West, Florida

• Jan 17–24, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,634 ($519/night)

]]> https://www.redweek.com/posting/R1510582 Thu, 27 Aug 2026 12:24:52 -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

The Galleon Resort

Key West, Florida

• Jan 23–30, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,976 ($854/night)

]]> https://www.redweek.com/posting/R1519976 Wed, 09 Sep 2026 13:48:04 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 24–31, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,665 ($381/night)

]]> https://www.redweek.com/posting/R1517513 Fri, 28 Aug 2026 14:36:57 -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 Verified & Protected

The Galleon Resort

Key West, Florida

• Jan 30 – Feb 13, 2027 (14 nights)
• 2 bed/2 bath, sleeps 6
• $11,470 ($819/night)

]]> https://www.redweek.com/posting/R1520881 Fri, 11 Sep 2026 13:06:12 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jan 30 – Feb 6, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,306 ($472/night)

]]> https://www.redweek.com/posting/R1523493 Wed, 09 Sep 2026 14:28:25 -0700 Verified & Protected

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 Sun, 09 Aug 2026 11:36:04 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jan 31 – Feb 4, 2027 (4 nights)
• Studio/1 bath, sleeps 2
• $2,205 ($551/night)

]]> https://www.redweek.com/posting/R1506454 Thu, 13 Aug 2026 08:25:28 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jan 31 – Feb 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1474605 Wed, 20 May 2026 14:53:42 -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/R1494038 Thu, 30 Jul 2026 09:28:36 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Feb 6–13, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,268 ($467/night)

]]> https://www.redweek.com/posting/R1526459 Wed, 16 Sep 2026 15:57:42 -0700 Verified & Protected

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 Sun, 09 Aug 2026 11:37:51 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Feb 7–14, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1521636 Wed, 09 Sep 2026 14:58:34 -0700