https://www.redweek.com/featured/spring-summer-rentals/North+America/United+States/Florida/The+Keys?sort=date en Mon, 06 Apr 2026 00:29:39 -0700 3600 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Apr 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1448909 Wed, 25 Mar 2026 08:09:18 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• May 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1440313 Fri, 13 Mar 2026 08:56:06 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1421625 Fri, 13 Feb 2026 11:11:56 -0800 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• May 3–7, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,220 ($305/night)

]]> https://www.redweek.com/posting/R1441995 Fri, 13 Mar 2026 11:20:43 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• May 3–7, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,220 ($305/night)

]]> https://www.redweek.com/posting/R1441983 Fri, 13 Mar 2026 11:21:11 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• May 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1443246 Tue, 31 Mar 2026 12:56:11 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1440661 Mon, 09 Mar 2026 09:22:57 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1428108 Mon, 09 Feb 2026 13:02:36 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 10–17, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1453079 Wed, 01 Apr 2026 13:34:49 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 10–14, 2026 (4 nights)
• Studio/1 bath, sleeps 2
• $2,423 ($606/night)

]]> https://www.redweek.com/posting/R1338148 Wed, 17 Sep 2025 06:26:21 -0700 Verified & Protected

Tranquility Bay Resort

Marathon, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,096 ($299/night)

]]> https://www.redweek.com/posting/R1445320 Tue, 24 Mar 2026 14:15:20 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,058 ($580/night)

]]> https://www.redweek.com/posting/R1444471 Thu, 12 Mar 2026 08:37:51 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,058 ($580/night)

]]> https://www.redweek.com/posting/R1440630 Thu, 12 Mar 2026 08:39:11 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1453097 Wed, 01 Apr 2026 13:34:54 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• May 17–23, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $2,314 ($386/night)

]]> https://www.redweek.com/posting/R1433209 Mon, 09 Mar 2026 07:37:23 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 17–24, 2026 (7 nights)
• 2 bed/2.5 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1442920 Tue, 24 Mar 2026 14:44:56 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 18–21, 2026 (3 nights)
• Studio/1 bath, sleeps 2
• $583 ($194/night)

]]> https://www.redweek.com/posting/R1391063 Thu, 04 Dec 2025 11:11:15 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• May 19–22, 2026 (3 nights)
• 2 bed/2 bath, sleeps 6
• $1,165 ($388/night)

]]> https://www.redweek.com/posting/R1450512 Tue, 24 Mar 2026 14:58:29 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• May 21–25, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,878 ($470/night)

]]> https://www.redweek.com/posting/R1449790 Mon, 30 Mar 2026 16:35:24 -0700 Verified & Protected

Tranquility Bay Resort

Marathon, Florida

• May 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1445340 Tue, 24 Mar 2026 14:15:33 -0700 Verified & Protected

Coconut Beach Resort

Key West, Florida

• May 23–30, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1439619 Tue, 17 Mar 2026 13:46:55 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,568 ($510/night)

]]> https://www.redweek.com/posting/R1425979 Mon, 23 Feb 2026 11:50:16 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,565 ($366/night)

]]> https://www.redweek.com/posting/R1415686 Fri, 30 Jan 2026 08:43:41 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1450481 Mon, 30 Mar 2026 06:51:33 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• May 24–29, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,982 ($396/night)

]]> https://www.redweek.com/posting/R1356624 Sat, 01 Nov 2025 08:36:03 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 29–31, 2026 (2 nights)
• Studio/1 bath, sleeps 2
• $610 ($305/night)

]]> https://www.redweek.com/posting/R1414341 Thu, 22 Jan 2026 13:49:33 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 31 – Jun 4, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,987 ($497/night)

]]> https://www.redweek.com/posting/R1421534 Wed, 18 Feb 2026 12:39:22 -0800 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1391609 Mon, 08 Dec 2025 08:16:29 -0800 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• May 31 – Jun 6, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $2,313 ($385/night)

]]> https://www.redweek.com/posting/R1454129 Thu, 02 Apr 2026 14:34:41 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1406396 Fri, 09 Jan 2026 11:27:17 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jun 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,404 ($486/night)

]]> https://www.redweek.com/posting/R1434837 Wed, 11 Mar 2026 11:48:31 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1421627 Thu, 29 Jan 2026 13:06:46 -0800

The Galleon Resort

Key West, Florida

• Jun 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1455677 Thu, 02 Apr 2026 10:35:33 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1338915 Fri, 19 Sep 2025 05:41:26 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Jun 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,535 ($505/night)

]]> https://www.redweek.com/posting/R1451453 Fri, 03 Apr 2026 11:19:00 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jun 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1395988 Tue, 20 Jan 2026 13:46:44 -0800

The Galleon Resort

Key West, Florida

• Jun 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1455679 Thu, 02 Apr 2026 10:35:33 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,512 ($502/night)

]]> https://www.redweek.com/posting/R1409697 Tue, 30 Dec 2025 18:25:06 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,568 ($510/night)

]]> https://www.redweek.com/posting/R1413244 Tue, 13 Jan 2026 13:43:40 -0800 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Jun 14–20, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $3,949 ($658/night)

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

Hyatt Beach House Resort

Key West, Florida

• Jun 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1449660 Sat, 21 Mar 2026 14:45:02 -0700

Hyatt Windward Pointe Resort

Key West, Florida

• Jun 14–18, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,110 ($278/night)

]]> https://www.redweek.com/posting/R1450703 Tue, 24 Mar 2026 08:53:26 -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

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 Mon, 12 Jan 2026 13:19:18 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1433942 Wed, 18 Feb 2026 13:35:16 -0800 Verified & Protected

Coconut Beach Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,404 ($486/night)

]]> https://www.redweek.com/posting/R1442605 Thu, 02 Apr 2026 12:58:40 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Jun 27 – Jul 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,568 ($510/night)

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

Hyatt Beach House Resort

Key West, Florida

• Jun 28 – Jul 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,403 ($486/night)

]]> https://www.redweek.com/posting/R1434711 Mon, 23 Feb 2026 06:58:59 -0800