https://www.redweek.com/featured/fall-rentals/North+America/United+States/Florida/Kissimmee en Sat, 15 Aug 2026 14:18:01 -0700 3600 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 1–4, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $336 ($112/night)

]]> https://www.redweek.com/posting/R1511053 Tue, 11 Aug 2026 23:21:38 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 1–4, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $243 ($81/night)

]]> https://www.redweek.com/posting/R1511052 Tue, 11 Aug 2026 23:21:38 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Sep 2–8, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($222/night)

]]> https://www.redweek.com/posting/R1496690 Tue, 14 Jul 2026 06:08:42 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• Sep 3–10, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1489201 Mon, 29 Jun 2026 08:50:05 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 4–11, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1442412 Fri, 06 Mar 2026 11:55:11 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• Sep 4–7, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $583 ($194/night)

]]> https://www.redweek.com/posting/R1494386 Thu, 09 Jul 2026 13:01:34 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $777 ($111/night)

]]> https://www.redweek.com/posting/R1504017 Tue, 28 Jul 2026 15:51:43 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,536 ($219/night)

]]> https://www.redweek.com/posting/R1441189 Wed, 04 Mar 2026 06:11:01 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1441603 Thu, 05 Mar 2026 04:53:44 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 11–18, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,757 ($251/night)

]]> https://www.redweek.com/posting/R1510068 Mon, 10 Aug 2026 06:24:55 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1444262 Tue, 10 Mar 2026 11:32:42 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 12–19, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $520 ($74/night)

]]> https://www.redweek.com/posting/R1456202 Fri, 03 Apr 2026 05:39:28 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 12–15, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $250 ($83/night)

]]> https://www.redweek.com/posting/R1509792 Sun, 09 Aug 2026 13:24:45 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1443622 Tue, 10 Mar 2026 05:12:37 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 12–18, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $402 ($67/night)

]]> https://www.redweek.com/posting/R1464040 Wed, 22 Apr 2026 04:56:37 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 13–20, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $511 ($73/night)

]]> https://www.redweek.com/posting/R1450639 Tue, 24 Mar 2026 07:19:01 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 13–19, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $393 ($65/night)

]]> https://www.redweek.com/posting/R1491661 Wed, 01 Jul 2026 20:31:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 13–21, 2026 (8 nights)
• 1 bed/1 bath, sleeps 4
• $566 ($71/night)

]]> https://www.redweek.com/posting/R1502031 Thu, 23 Jul 2026 11:51:40 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 14–21, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $492 ($70/night)

]]> https://www.redweek.com/posting/R1506522 Sun, 02 Aug 2026 11:05:34 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 14–18, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $243 ($61/night)

]]> https://www.redweek.com/posting/R1511497 Wed, 12 Aug 2026 17:43:38 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 14–20, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $445 ($74/night)

]]> https://www.redweek.com/posting/R1506854 Mon, 03 Aug 2026 09:12:53 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 15–22, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $492 ($70/night)

]]> https://www.redweek.com/posting/R1505352 Thu, 30 Jul 2026 11:59:07 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 16–20, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $352 ($88/night)

]]> https://www.redweek.com/posting/R1510227 Mon, 10 Aug 2026 10:45:51 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 16–19, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $250 ($83/night)

]]> https://www.redweek.com/posting/R1498947 Thu, 16 Jul 2026 11:53:49 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 16–21, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $399 ($80/night)

]]> https://www.redweek.com/posting/R1505221 Thu, 30 Jul 2026 08:30:29 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 16–23, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $492 ($70/night)

]]> https://www.redweek.com/posting/R1512324 Fri, 14 Aug 2026 21:50:59 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 17–23, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $456 ($76/night)

]]> https://www.redweek.com/posting/R1499486 Fri, 17 Jul 2026 15:52:37 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 17–24, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $511 ($73/night)

]]> https://www.redweek.com/posting/R1501729 Wed, 22 Jul 2026 17:37:52 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 18–23, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $399 ($80/night)

]]> https://www.redweek.com/posting/R1508174 Wed, 05 Aug 2026 13:06:59 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,536 ($219/night)

]]> https://www.redweek.com/posting/R1440392 Tue, 03 Mar 2026 04:50:03 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• Sep 18–20, 2026 (2 nights)
• 3 bed/3 bath, sleeps 12
• $455 ($228/night)

]]> https://www.redweek.com/posting/R1433488 Wed, 11 Mar 2026 14:37:52 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,536 ($219/night)

]]> https://www.redweek.com/posting/R1443717 Tue, 10 Mar 2026 05:09:33 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 18–22, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $352 ($88/night)

]]> https://www.redweek.com/posting/R1493886 Mon, 06 Jul 2026 07:08:36 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1449146 Fri, 17 Apr 2026 05:04:18 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1443700 Tue, 10 Mar 2026 05:11:10 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,198 ($171/night)

]]> https://www.redweek.com/posting/R1444703 Wed, 11 Mar 2026 10:16:19 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• Sep 18–20, 2026 (2 nights)
• 3 bed/3 bath, sleeps 12
• $455 ($228/night)

]]> https://www.redweek.com/posting/R1433660 Wed, 11 Mar 2026 14:01:17 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1449139 Fri, 17 Apr 2026 05:02:14 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 20–27, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1450197 Fri, 17 Apr 2026 05:08:41 -0700 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• Sep 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $995 ($142/night)

]]> https://www.redweek.com/posting/R1471805 Thu, 14 May 2026 14:33:36 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 21–25, 2026 (4 nights)
• 2 bed/2 bath, sleeps 10
• $1,544 ($386/night)

]]> https://www.redweek.com/posting/R1489929 Mon, 29 Jun 2026 17:49:51 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Sep 25 – Oct 2, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,856 ($265/night)

]]> https://www.redweek.com/posting/R1430184 Wed, 04 Mar 2026 09:00:17 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 25 – Oct 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1451219 Fri, 17 Apr 2026 05:26:08 -0700 Verified & Protected

Westgate Towers

Kissimmee, Florida

• Sep 25 – Oct 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,354 ($193/night)

]]> https://www.redweek.com/posting/R1447693 Fri, 17 Apr 2026 04:37:12 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Sep 25 – Oct 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1448353 Fri, 17 Apr 2026 04:50:52 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Sep 26 – Oct 3, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,849 ($264/night)

]]> https://www.redweek.com/posting/R1509434 Thu, 13 Aug 2026 07:52:51 -0700 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• Sep 26 – Oct 3, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1470065 Thu, 07 May 2026 11:03:24 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Sep 27–30, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $196 ($65/night)

]]> https://www.redweek.com/posting/R1506003 Sat, 01 Aug 2026 01:51:48 -0700