https://www.redweek.com/featured/fall-rentals/North+America/United+States/Florida/The+Keys en Sat, 15 Aug 2026 14:17:52 -0700 3600 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Sep 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,311 ($187/night)

]]> https://www.redweek.com/posting/R1485875 Thu, 18 Jun 2026 09:18:19 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Sep 6–12, 2026 (6 nights)
• Studio/1 bath, sleeps 2
• $999 ($166/night)

]]> https://www.redweek.com/posting/R1459206 Tue, 14 Apr 2026 14:04:47 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Sep 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,123 ($303/night)

]]> https://www.redweek.com/posting/R1477928 Mon, 01 Jun 2026 19:29:51 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Sep 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1406132 Tue, 30 Dec 2025 18:39:54 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Sep 6–10, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,110 ($278/night)

]]> https://www.redweek.com/posting/R1511776 Fri, 14 Aug 2026 09:39:12 -0700 Verified & Protected

Anchorage Resort & Yacht Club

Key Largo, Florida

• Sep 12–19, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1473810 Mon, 06 Jul 2026 07:02:02 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

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

]]> https://www.redweek.com/posting/R1499795 Mon, 20 Jul 2026 06:58:29 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Sep 13–19, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $1,330 ($222/night)

]]> https://www.redweek.com/posting/R1501050 Thu, 23 Jul 2026 17:58:28 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Sep 19–26, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1471546 Thu, 18 Jun 2026 07:49:17 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Sep 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,810 ($401/night)

]]> https://www.redweek.com/posting/R1500731 Thu, 30 Jul 2026 07:37:31 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Sep 19–26, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1501821 Wed, 29 Jul 2026 13:17:03 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Sep 20–24, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,330 ($332/night)

]]> https://www.redweek.com/posting/R1511349 Thu, 13 Aug 2026 07:26:54 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

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

]]> https://www.redweek.com/posting/R1510726 Fri, 14 Aug 2026 13:28:37 -0700

The Galleon Resort

Key West, Florida

• Sep 27 – Oct 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,069 ($438/night)

]]> https://www.redweek.com/posting/R1512428 Sat, 15 Aug 2026 10:33:08 -0700

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,467 ($352/night)

]]> https://www.redweek.com/posting/R1512457 Sat, 15 Aug 2026 11:45:38 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1509647 Mon, 10 Aug 2026 12:16:35 -0700 Verified & Protected

Caloosa Cove Resort

Islamorada, Florida

• Oct 10–17, 2026 (7 nights)
• Studio/1 bath, sleeps 3
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1424981 Tue, 24 Feb 2026 10:44:18 -0800 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,532 ($362/night)

]]> https://www.redweek.com/posting/R1403021 Fri, 19 Dec 2025 12:19:00 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Oct 11–15, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,220 ($305/night)

]]> https://www.redweek.com/posting/R1407721 Mon, 05 Jan 2026 13:44:46 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Oct 15–18, 2026 (3 nights)
• 2 bed/2.5 bath, sleeps 6
• $1,987 ($662/night)

]]> https://www.redweek.com/posting/R1506058 Mon, 10 Aug 2026 12:05:31 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1478671 Tue, 23 Jun 2026 08:53:15 -0700 Verified & Protected

Coconut Mallory Marina & Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,932 ($276/night)

]]> https://www.redweek.com/posting/R1350231 Wed, 15 Oct 2025 13:52:42 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1443772 Thu, 02 Apr 2026 06:45:38 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1483442 Wed, 17 Jun 2026 14:36:23 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $8,418 ($1,203/night)

]]> https://www.redweek.com/posting/R1496430 Fri, 31 Jul 2026 08:03:31 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,069 ($438/night)

]]> https://www.redweek.com/posting/R1505475 Fri, 31 Jul 2026 14:27:52 -0700 Verified & Protected

Coconut Mallory Marina & Resort

Key West, Florida

• Oct 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,467 ($352/night)

]]> https://www.redweek.com/posting/R1506607 Wed, 05 Aug 2026 12:28:20 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1507946 Mon, 10 Aug 2026 11:16:37 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,848 ($407/night)

]]> https://www.redweek.com/posting/R1502378 Fri, 24 Jul 2026 11:44:32 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1470063 Thu, 07 May 2026 11:23:12 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 18–22, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,440 ($360/night)

]]> https://www.redweek.com/posting/R1474245 Tue, 26 May 2026 18:56:43 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1472359 Thu, 21 May 2026 12:10:11 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1418721 Fri, 13 Feb 2026 11:17:48 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,859 ($408/night)

]]> https://www.redweek.com/posting/R1427473 Fri, 20 Feb 2026 07:57:23 -0800

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1509240 Fri, 07 Aug 2026 17:26:59 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 20–24, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $2,201 ($550/night)

]]> https://www.redweek.com/posting/R1447376 Fri, 03 Apr 2026 11:01:17 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1507654 Fri, 07 Aug 2026 15:48:28 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,946 ($707/night)

]]> https://www.redweek.com/posting/R1442637 Tue, 10 Mar 2026 15:36:23 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 24–27, 2026 (3 nights)
• 2 bed/2 bath, sleeps 6
• $1,807 ($602/night)

]]> https://www.redweek.com/posting/R1507015 Mon, 03 Aug 2026 14:50:48 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1465865 Mon, 11 May 2026 11:21:25 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 31 – Nov 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1483417 Fri, 19 Jun 2026 13:23:46 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Nov 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1498815 Fri, 17 Jul 2026 07:44:24 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Nov 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,672 ($667/night)

]]> https://www.redweek.com/posting/R1487488 Sat, 15 Aug 2026 12:57:57 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Nov 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1431151 Wed, 04 Mar 2026 13:03:11 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• Nov 14–16, 2026 (2 nights)
• 1 bed/1 bath, sleeps 4
• $666 ($333/night)

]]> https://www.redweek.com/posting/R1462945 Fri, 24 Apr 2026 08:46:15 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Nov 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1440016 Mon, 23 Mar 2026 10:56:56 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• Nov 15–19, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,987 ($497/night)

]]> https://www.redweek.com/posting/R1508612 Thu, 06 Aug 2026 12:47:12 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Nov 20–24, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,660 ($415/night)

]]> https://www.redweek.com/posting/R1491273 Mon, 06 Jul 2026 07:08:56 -0700