https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/Kissimmee en Fri, 05 Jun 2026 22:57:29 -0700 3600 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,756 ($251/night)

]]> https://www.redweek.com/posting/R1480354 Thu, 04 Jun 2026 21:10:18 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,290 ($184/night)

]]> https://www.redweek.com/posting/R1480353 Thu, 04 Jun 2026 21:10:18 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–8, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $919 ($131/night)

]]> https://www.redweek.com/posting/R1480352 Thu, 04 Jun 2026 21:10:18 -0700 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 4–18, 2026 (14 nights)
• 1 bed/1 bath, sleeps 4
• $1,673 ($120/night)

]]> https://www.redweek.com/posting/R1479902 Wed, 03 Jun 2026 17:57:04 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 4–18, 2026 (14 nights)
• 2 bed/2 bath, sleeps 8
• $3,199 ($229/night)

]]> https://www.redweek.com/posting/R1479904 Wed, 03 Jun 2026 17:57:04 -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
• $1,211 ($173/night)

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

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 4–18, 2026 (14 nights)
• 2 bed/2 bath, sleeps 8
• $2,406 ($172/night)

]]> https://www.redweek.com/posting/R1479903 Wed, 03 Jun 2026 17:57:04 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1462189 Fri, 17 Apr 2026 07:41:31 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1462188 Fri, 17 Apr 2026 07:41:31 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1462187 Fri, 17 Apr 2026 07:41:31 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 6–9, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $639 ($213/night)

]]> https://www.redweek.com/posting/R1464440 Thu, 23 Apr 2026 03:00:27 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 6–9, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $355 ($118/night)

]]> https://www.redweek.com/posting/R1464438 Thu, 23 Apr 2026 03:00:27 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 6–9, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $499 ($166/night)

]]> https://www.redweek.com/posting/R1464439 Thu, 23 Apr 2026 03:00:27 -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

Vacation Village at Parkway

Kissimmee, Florida

• Dec 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,932 ($276/night)

]]> https://www.redweek.com/posting/R1443982 Thu, 23 Apr 2026 14:50:48 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,211 ($173/night)

]]> https://www.redweek.com/posting/R1480356 Thu, 04 Jun 2026 21:10:29 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,612 ($230/night)

]]> https://www.redweek.com/posting/R1480357 Thu, 04 Jun 2026 21:10:29 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 14–21, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $839 ($120/night)

]]> https://www.redweek.com/posting/R1480355 Thu, 04 Jun 2026 21:10:29 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–21, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $946 ($189/night)

]]> https://www.redweek.com/posting/R1475921 Sat, 23 May 2026 20:23:43 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–21, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $679 ($136/night)

]]> https://www.redweek.com/posting/R1475920 Sat, 23 May 2026 20:23:43 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–22, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $1,079 ($180/night)

]]> https://www.redweek.com/posting/R1479810 Wed, 03 Jun 2026 13:54:13 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–22, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $1,462 ($244/night)

]]> https://www.redweek.com/posting/R1479811 Wed, 03 Jun 2026 13:54:13 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–21, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $1,312 ($262/night)

]]> https://www.redweek.com/posting/R1475922 Sat, 23 May 2026 20:23:43 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 16–22, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $759 ($127/night)

]]> https://www.redweek.com/posting/R1479809 Wed, 03 Jun 2026 13:54:13 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 17–21, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $599 ($150/night)

]]> https://www.redweek.com/posting/R1480358 Thu, 04 Jun 2026 21:11:01 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 17–21, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $813 ($203/night)

]]> https://www.redweek.com/posting/R1480359 Thu, 04 Jun 2026 21:11:01 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 17–21, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $1,163 ($291/night)

]]> https://www.redweek.com/posting/R1480360 Thu, 04 Jun 2026 21:11:01 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–27, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $1,660 ($184/night)

]]> https://www.redweek.com/posting/R1479962 Wed, 03 Jun 2026 21:39:37 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–27, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $2,275 ($253/night)

]]> https://www.redweek.com/posting/R1479963 Wed, 03 Jun 2026 21:39:37 -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

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–26, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $1,943 ($243/night)

]]> https://www.redweek.com/posting/R1473605 Sun, 17 May 2026 17:26:48 -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 18–26, 2026 (8 nights)
• 1 bed/1 bath, sleeps 4
• $1,012 ($127/night)

]]> https://www.redweek.com/posting/R1473603 Sun, 17 May 2026 17:26:48 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 18–27, 2026 (9 nights)
• 1 bed/1 bath, sleeps 4
• $1,185 ($132/night)

]]> https://www.redweek.com/posting/R1479961 Wed, 03 Jun 2026 21:39:37 -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 18–26, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $1,436 ($179/night)

]]> https://www.redweek.com/posting/R1473604 Sun, 17 May 2026 17:26:48 -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
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1477781 Fri, 29 May 2026 09:31:23 -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 19–26, 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

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1472387 Thu, 14 May 2026 13:25:04 -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

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1468477 Tue, 05 May 2026 07:20:28 -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
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1468481 Tue, 05 May 2026 07:17:10 -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