https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/Kissimmee?sort=date en Tue, 14 Apr 2026 17:47:11 -0700 3600 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $937 ($234/night)

]]> https://www.redweek.com/posting/R1453025 Fri, 27 Mar 2026 11:54:13 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $706 ($176/night)

]]> https://www.redweek.com/posting/R1453024 Fri, 27 Mar 2026 11:54:13 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1460672 Mon, 13 Apr 2026 17:56:05 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,022 ($432/night)

]]> https://www.redweek.com/posting/R1430189 Wed, 04 Mar 2026 08:56:26 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1460673 Mon, 13 Apr 2026 17:56:05 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1460671 Mon, 13 Apr 2026 17:56:05 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 5–8, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $439 ($146/night)

]]> https://www.redweek.com/posting/R1457085 Sun, 05 Apr 2026 19:49:21 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 5–8, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $586 ($195/night)

]]> https://www.redweek.com/posting/R1457086 Sun, 05 Apr 2026 19:49:21 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 5–8, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $826 ($275/night)

]]> https://www.redweek.com/posting/R1457087 Sun, 05 Apr 2026 19:49:21 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1459965 Sun, 12 Apr 2026 06:40:46 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1459964 Sun, 12 Apr 2026 06:40:46 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 7–14, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1459963 Sun, 12 Apr 2026 06:40:46 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1447720 Tue, 17 Mar 2026 11:06:34 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 8–15, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1447718 Tue, 17 Mar 2026 11:06:34 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1447719 Tue, 17 Mar 2026 11:06:34 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–20, 2026 (9 nights)
• 1 bed/1 bath, sleeps 4
• $1,185 ($132/night)

]]> https://www.redweek.com/posting/R1448822 Thu, 19 Mar 2026 14:40:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–16, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $946 ($189/night)

]]> https://www.redweek.com/posting/R1460544 Mon, 13 Apr 2026 15:17:34 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–19, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $1,436 ($179/night)

]]> https://www.redweek.com/posting/R1447743 Tue, 17 Mar 2026 11:28:28 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–19, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $1,943 ($243/night)

]]> https://www.redweek.com/posting/R1447744 Tue, 17 Mar 2026 11:28:28 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–16, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $1,312 ($262/night)

]]> https://www.redweek.com/posting/R1460545 Mon, 13 Apr 2026 15:17:34 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–20, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $2,275 ($253/night)

]]> https://www.redweek.com/posting/R1448824 Thu, 19 Mar 2026 14:40:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–20, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $1,660 ($184/night)

]]> https://www.redweek.com/posting/R1448823 Thu, 19 Mar 2026 14:40:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–19, 2026 (8 nights)
• 1 bed/1 bath, sleeps 4
• $1,012 ($127/night)

]]> https://www.redweek.com/posting/R1447742 Tue, 17 Mar 2026 11:28:28 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 11–16, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $679 ($136/night)

]]> https://www.redweek.com/posting/R1460543 Mon, 13 Apr 2026 15:17:34 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Dec 12–19, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1430187 Wed, 04 Mar 2026 09:08:21 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–20, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $511 ($128/night)

]]> https://www.redweek.com/posting/R1457402 Mon, 06 Apr 2026 13:43:24 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–20, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $977 ($244/night)

]]> https://www.redweek.com/posting/R1457404 Mon, 06 Apr 2026 13:43:24 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–20, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $719 ($180/night)

]]> https://www.redweek.com/posting/R1457403 Mon, 06 Apr 2026 13:43:24 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Dec 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1425604 Wed, 18 Feb 2026 10:36:10 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Dec 18–25, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1421758 Thu, 22 Jan 2026 02:12:51 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1456716 Sat, 04 Apr 2026 13:13:36 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1456714 Sat, 04 Apr 2026 13:13:36 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1456715 Sat, 04 Apr 2026 13:13:36 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Dec 18–25, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1421719 Thu, 22 Jan 2026 02:08:47 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–27, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $1,436 ($179/night)

]]> https://www.redweek.com/posting/R1458707 Thu, 09 Apr 2026 02:48:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–27, 2026 (8 nights)
• 1 bed/1 bath, sleeps 4
• $1,012 ($127/night)

]]> https://www.redweek.com/posting/R1458706 Thu, 09 Apr 2026 02:48:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–27, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $1,943 ($243/night)

]]> https://www.redweek.com/posting/R1458708 Thu, 09 Apr 2026 02:48:22 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19, 2026 – Jan 2, 2027 (14 nights)
• 2 bed/2 bath, sleeps 8
• $3,247 ($232/night)

]]> https://www.redweek.com/posting/R1451091 Wed, 25 Mar 2026 06:30:06 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1436867 Wed, 11 Mar 2026 14:47:44 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1444204 Fri, 13 Mar 2026 09:27:44 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1447327 Mon, 16 Mar 2026 15:00:38 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,198 ($171/night)

]]> https://www.redweek.com/posting/R1427776 Tue, 03 Feb 2026 09:29:02 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–23, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $511 ($128/night)

]]> https://www.redweek.com/posting/R1457575 Mon, 06 Apr 2026 19:03:09 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1447328 Mon, 16 Mar 2026 15:00:38 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–23, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $719 ($180/night)

]]> https://www.redweek.com/posting/R1457576 Mon, 06 Apr 2026 19:03:09 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1447326 Mon, 16 Mar 2026 15:00:38 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19, 2026 – Jan 2, 2027 (14 nights)
• 1 bed/1 bath, sleeps 4
• $1,699 ($121/night)

]]> https://www.redweek.com/posting/R1451089 Wed, 25 Mar 2026 06:30:06 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1444174 Fri, 13 Mar 2026 09:25:29 -0700