https://www.redweek.com/featured/spring-summer-rentals/North+America/United+States/Florida/The+Keys en Tue, 26 May 2026 09:44:48 -0700 3600 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jun 14–20, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $1,660 ($277/night)

]]> https://www.redweek.com/posting/R1421538 Wed, 18 Feb 2026 12:37:24 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jun 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,173 ($453/night)

]]> https://www.redweek.com/posting/R1463883 Thu, 23 Apr 2026 15:20:20 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jun 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,660 ($237/night)

]]> https://www.redweek.com/posting/R1449660 Wed, 15 Apr 2026 14:56:51 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Jun 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1430152 Mon, 06 Apr 2026 08:33:08 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,886 ($412/night)

]]> https://www.redweek.com/posting/R1463020 Wed, 06 May 2026 13:55:37 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,886 ($412/night)

]]> https://www.redweek.com/posting/R1463021 Wed, 06 May 2026 13:57:10 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,486 ($498/night)

]]> https://www.redweek.com/posting/R1416632 Tue, 07 Apr 2026 10:24:14 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,745 ($392/night)

]]> https://www.redweek.com/posting/R1466591 Wed, 29 Apr 2026 11:58:02 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,512 ($502/night)

]]> https://www.redweek.com/posting/R1409699 Tue, 30 Dec 2025 18:25:06 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,072 ($439/night)

]]> https://www.redweek.com/posting/R1442973 Wed, 18 Mar 2026 10:51:46 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jun 28 – Jul 2, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,082 ($271/night)

]]> https://www.redweek.com/posting/R1467794 Fri, 01 May 2026 13:55:01 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 28 – Jul 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,382 ($626/night)

]]> https://www.redweek.com/posting/R1468501 Wed, 20 May 2026 07:42:40 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jun 28 – Jul 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1394774 Thu, 29 Jan 2026 07:00:31 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jun 28 – Jul 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,987 ($284/night)

]]> https://www.redweek.com/posting/R1473761 Wed, 20 May 2026 10:52:23 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 29 – Jul 3, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,440 ($360/night)

]]> https://www.redweek.com/posting/R1468758 Tue, 05 May 2026 07:55:52 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 1–5, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,987 ($497/night)

]]> https://www.redweek.com/posting/R1414796 Fri, 30 Jan 2026 12:52:47 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 3–6, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $1,649 ($550/night)

]]> https://www.redweek.com/posting/R1447266 Fri, 03 Apr 2026 12:35:18 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,072 ($439/night)

]]> https://www.redweek.com/posting/R1457869 Thu, 16 Apr 2026 12:21:16 -0700

The Galleon Resort

Key West, Florida

• Jul 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1456579 Sat, 04 Apr 2026 06:52:52 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jul 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1470062 Thu, 07 May 2026 12:14:30 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jul 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1443824 Wed, 18 Mar 2026 10:58:33 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Jul 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,123 ($303/night)

]]> https://www.redweek.com/posting/R1466622 Thu, 30 Apr 2026 07:08:44 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,839 ($548/night)

]]> https://www.redweek.com/posting/R1428368 Tue, 24 Feb 2026 12:37:41 -0800

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1473600 Sun, 17 May 2026 17:04:38 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 12–16, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,312 ($328/night)

]]> https://www.redweek.com/posting/R1443534 Wed, 11 Mar 2026 13:58:45 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jul 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,640 ($377/night)

]]> https://www.redweek.com/posting/R1474665 Wed, 20 May 2026 14:08:45 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jul 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,640 ($377/night)

]]> https://www.redweek.com/posting/R1474689 Thu, 21 May 2026 08:01:08 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Jul 18–25, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1428323 Wed, 18 Mar 2026 08:31:04 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Jul 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,280 ($469/night)

]]> https://www.redweek.com/posting/R1475424 Mon, 25 May 2026 10:27:12 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jul 18–25, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $1,932 ($276/night)

]]> https://www.redweek.com/posting/R1338004 Tue, 16 Sep 2025 14:49:49 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jul 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1338002 Tue, 16 Sep 2025 14:45:51 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1462794 Mon, 27 Apr 2026 07:49:38 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

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

]]> https://www.redweek.com/posting/R1409491 Mon, 16 Feb 2026 09:57:45 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

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

]]> https://www.redweek.com/posting/R1423078 Fri, 13 Feb 2026 12:41:03 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jul 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1405233 Wed, 24 Dec 2025 12:25:05 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jul 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1446981 Fri, 03 Apr 2026 10:55:01 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jul 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1476253 Tue, 26 May 2026 07:12:14 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jul 25 – Aug 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,276 ($611/night)

]]> https://www.redweek.com/posting/R1453659 Mon, 20 Apr 2026 17:06:52 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jul 25 – Aug 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,821 ($689/night)

]]> https://www.redweek.com/posting/R1449912 Thu, 26 Mar 2026 07:19:29 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jul 26 – Aug 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,859 ($408/night)

]]> https://www.redweek.com/posting/R1414316 Tue, 27 Jan 2026 16:52:12 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jul 26 – Aug 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1465592 Wed, 29 Apr 2026 08:19:25 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jul 26 – Aug 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,914 ($416/night)

]]> https://www.redweek.com/posting/R1405127 Fri, 26 Dec 2025 07:47:37 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 26 – Aug 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,112 ($588/night)

]]> https://www.redweek.com/posting/R1419314 Tue, 03 Feb 2026 17:34:21 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jul 26 – Aug 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1469120 Thu, 07 May 2026 08:31:54 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jul 26 – Aug 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1414798 Fri, 30 Jan 2026 13:04:54 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• Aug 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,948 ($564/night)

]]> https://www.redweek.com/posting/R1460303 Mon, 13 Apr 2026 08:12:37 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Aug 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,166 ($595/night)

]]> https://www.redweek.com/posting/R1460305 Mon, 13 Apr 2026 08:12:37 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Aug 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1447963 Mon, 23 Mar 2026 08:28:53 -0700