https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/Kissimmee?sort=date en Sun, 05 Apr 2026 15:07:26 -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
• $830 ($208/night)

]]> https://www.redweek.com/posting/R1453026 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

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 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)
• 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 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 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 11–20, 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 11–19, 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 11–20, 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)
• 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

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 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/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

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/R1421719 Thu, 22 Jan 2026 02:08:47 -0800

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,053 ($579/night)

]]> https://www.redweek.com/posting/R1455722 Thu, 02 Apr 2026 12:15:51 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 19, 2026 – Jan 2, 2027 (14 nights)
• 2 bed/2 bath, sleeps 8
• $2,462 ($176/night)

]]> https://www.redweek.com/posting/R1451090 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 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 19–26, 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 19–26, 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

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

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

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
• $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)
• 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 20, 2026 – Jan 3, 2027 (14 nights)
• 2 bed/2 bath, sleeps 8
• $3,112 ($222/night)

]]> https://www.redweek.com/posting/R1452661 Thu, 26 Mar 2026 21:37:16 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20, 2026 – Jan 3, 2027 (14 nights)
• 2 bed/2 bath, sleeps 8
• $2,397 ($171/night)

]]> https://www.redweek.com/posting/R1452660 Thu, 26 Mar 2026 21:37:16 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1451659 Thu, 26 Mar 2026 09:24:41 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20–23, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $355 ($118/night)

]]> https://www.redweek.com/posting/R1451420 Wed, 25 Mar 2026 16:27:27 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1444185 Fri, 13 Mar 2026 09:26:38 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $2,586 ($370/night)

]]> https://www.redweek.com/posting/R1437644 Thu, 19 Mar 2026 11:22:41 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,022 ($432/night)

]]> https://www.redweek.com/posting/R1445870 Wed, 01 Apr 2026 14:10:47 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1451660 Thu, 26 Mar 2026 09:24:41 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1451661 Thu, 26 Mar 2026 09:24:41 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20–23, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $639 ($213/night)

]]> https://www.redweek.com/posting/R1451422 Wed, 25 Mar 2026 16:27:27 -0700

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,042 ($292/night)

]]> https://www.redweek.com/posting/R1451393 Wed, 25 Mar 2026 15:17:11 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 20–23, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $499 ($166/night)

]]> https://www.redweek.com/posting/R1451421 Wed, 25 Mar 2026 16:27:27 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,476 ($211/night)

]]> https://www.redweek.com/posting/R1436151 Wed, 11 Mar 2026 11:40:20 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Dec 21–26, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $1,605 ($321/night)

]]> https://www.redweek.com/posting/R1440509 Thu, 05 Mar 2026 13:52:01 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 21–28, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1451675 Thu, 26 Mar 2026 09:29:42 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 21–28, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1451677 Thu, 26 Mar 2026 09:29:42 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 21–28, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1451676 Thu, 26 Mar 2026 09:29:42 -0700