https://www.redweek.com/featured/fall-rentals/North+America/United+States/Florida en Thu, 08 Oct 2026 22:14:36 -0700 3600 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,550 ($200/night)

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

Hyatt Beach House Resort

Key West, Florida

• Oct 18–22, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,110 ($250/night)

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

Hyatt Beach House Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,314 ($300/night)

]]> https://www.redweek.com/posting/R1514194 Tue, 25 Aug 2026 09:42:09 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,619 ($340/night)

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

Hyatt Beach House Resort

Key West, Florida

• Oct 18–22, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,550 ($350/night)

]]> https://www.redweek.com/posting/R1516446 Tue, 25 Aug 2026 08:25:27 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,306 ($299/night)

]]> https://www.redweek.com/posting/R1519178 Mon, 31 Aug 2026 11:52:14 -0700 Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,314 ($300/night)

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

Marriott's Oceana Palms

Riviera Beach, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,268 ($425/night)

]]> https://www.redweek.com/posting/R1467397 Fri, 08 May 2026 10:03:35 -0700 Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,932 ($250/night)

]]> https://www.redweek.com/posting/R1509240 Thu, 27 Aug 2026 11:26:59 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• Oct 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,704 ($220/night)

]]> https://www.redweek.com/posting/R1520617 Thu, 03 Sep 2026 07:28:08 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 20–24, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,765 ($399/night)

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

Hyatt Windward Pointe Resort

Key West, Florida

• Oct 22–25, 2026 (3 nights)
• 2 bed/2 bath, sleeps 6
• $1,594 ($480/night)

]]> https://www.redweek.com/posting/R1532172 Wed, 30 Sep 2026 17:55:05 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 22–25, 2026 (3 nights)
• 2 bed/2 bath, sleeps 6
• $1,495 ($450/night)

]]> https://www.redweek.com/posting/R1532213 Wed, 30 Sep 2026 19:29:25 -0700 Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

• Oct 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,856 ($240/night)

]]> https://www.redweek.com/posting/R1424535 Thu, 29 Jan 2026 12:37:11 -0800 Verified & Protected

Eagle's Nest Beach Resort

Marco Island, Florida

• Oct 23 – Nov 6, 2026 (14 nights)
• 2 bed/2 bath, sleeps 6
• $5,366 ($350/night)

]]> https://www.redweek.com/posting/R1523925 Thu, 10 Sep 2026 13:52:39 -0700 Verified & Protected

Marriott's Villas at Doral

Miami, Florida

• Oct 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,153 ($410/night)

]]> https://www.redweek.com/posting/R1467566 Mon, 04 May 2026 11:47:01 -0700 Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

• Oct 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1532960 Fri, 02 Oct 2026 12:25:00 -0700 Verified & Protected

Summer Bay Orlando Resort

Clermont, Florida

• Oct 23–30, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,242 ($160/night)

]]> https://www.redweek.com/posting/R1530209 Fri, 25 Sep 2026 17:48:33 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• Oct 23–30, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1510413 Tue, 25 Aug 2026 11:32:18 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• Oct 23–30, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,306 ($299/night)

]]> https://www.redweek.com/posting/R1510414 Tue, 25 Aug 2026 11:30:11 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Oct 24–30, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $932 ($140/night)

]]> https://www.redweek.com/posting/R1512719 Mon, 17 Aug 2026 07:33:59 -0700 Verified & Protected

Summer Bay Orlando Resort

Clermont, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,001 ($259/night)

]]> https://www.redweek.com/posting/R1528637 Tue, 22 Sep 2026 06:31:55 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,242 ($160/night)

]]> https://www.redweek.com/posting/R1517005 Wed, 26 Aug 2026 07:48:45 -0700 Verified & Protected

Umbrella Beach Resort

Holmes Beach, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2.5 bath, sleeps 6
• $1,742 ($225/night)

]]> https://www.redweek.com/posting/R1486876 Mon, 22 Jun 2026 10:07:59 -0700 Verified & Protected

Parc Soleil by Hilton Grand Vacations

Orlando, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $932 ($120/night)

]]> https://www.redweek.com/posting/R1433889 Mon, 09 Mar 2026 08:06:51 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,428 ($315/night)

]]> https://www.redweek.com/posting/R1520157 Tue, 01 Sep 2026 19:15:59 -0700 Verified & Protected

Club Wyndham Panama City Beach

Panama City Beach, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,396 ($180/night)

]]> https://www.redweek.com/posting/R1525760 Tue, 15 Sep 2026 13:25:38 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 24–27, 2026 (3 nights)
• 2 bed/2 bath, sleeps 6
• $999 ($300/night)

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

Hyatt Beach House Resort

Key West, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,196 ($154/night)

]]> https://www.redweek.com/posting/R1534960 Wed, 07 Oct 2026 07:42:53 -0700 Verified & Protected

Westgate Lakes Resort & Spa

Orlando, Florida

• Oct 24–31, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $1,866 ($241/night)

]]> https://www.redweek.com/posting/R1424669 Tue, 27 Jan 2026 12:27:45 -0800 Verified & Protected

Hilton Grand Vacations at SeaWorld

Orlando, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,358 ($175/night)

]]> https://www.redweek.com/posting/R1515534 Thu, 27 Aug 2026 13:55:13 -0700 Verified & Protected

Hilton Grand Vacations at Tuscany Village

Orlando, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1507096 Wed, 05 Aug 2026 07:03:05 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,204 ($155/night)

]]> https://www.redweek.com/posting/R1533941 Mon, 05 Oct 2026 08:32:11 -0700 Verified & Protected

Club Wyndham Royal Vista

Pompano Beach, Florida

• Oct 24–28, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $599 ($135/night)

]]> https://www.redweek.com/posting/R1508989 Thu, 13 Aug 2026 07:18:14 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,886 ($375/night)

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

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Oct 24–29, 2026 (5 nights)
• 3 bed/2 bath, sleeps 10
• $1,082 ($195/night)

]]> https://www.redweek.com/posting/R1530666 Sun, 27 Sep 2026 12:56:21 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $971 ($125/night)

]]> https://www.redweek.com/posting/R1520260 Fri, 04 Sep 2026 06:46:53 -0700 Verified & Protected

Sheraton PGA Vacation Resort

Port St. Lucie, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,200 ($285/night)

]]> https://www.redweek.com/posting/R1526688 Thu, 17 Sep 2026 10:17:11 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1518084 Fri, 28 Aug 2026 12:06:22 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Oct 25–31, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $999 ($150/night)

]]> https://www.redweek.com/posting/R1523700 Thu, 10 Sep 2026 07:22:36 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

• Oct 25–30, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $610 ($110/night)

]]> https://www.redweek.com/posting/R1519617 Tue, 01 Sep 2026 07:56:25 -0700 Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

• Oct 25 – Nov 13, 2026 (19 nights)
• 1 bed/1 bath, sleeps 4
• $3,132 ($150/night)

]]> https://www.redweek.com/posting/R1526679 Thu, 17 Sep 2026 10:04:01 -0700 Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,550 ($200/night)

]]> https://www.redweek.com/posting/R1517686 Thu, 27 Aug 2026 13:22:30 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1520934 Thu, 03 Sep 2026 15:10:34 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,542 ($199/night)

]]> https://www.redweek.com/posting/R1497635 Tue, 14 Jul 2026 13:02:31 -0700 Verified & Protected

Marriott's Legends Edge at Bay Point

Panama City Beach, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $777 ($100/night)

]]> https://www.redweek.com/posting/R1475611 Mon, 25 May 2026 07:40:19 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

• Oct 25–30, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $610 ($110/night)

]]> https://www.redweek.com/posting/R1519616 Tue, 01 Sep 2026 07:56:58 -0700 Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,513 ($457/night)

]]> https://www.redweek.com/posting/R1453806 Sun, 29 Mar 2026 13:46:33 -0700