https://www.redweek.com/featured/winter-rentals/North+America/United+States/Florida/Kissimmee en Tue, 05 May 2026 19:22:41 -0700 3600 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 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 5–8, 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 5–12, 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 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 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 5–8, 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 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

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

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 11–16, 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

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

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

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

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 - 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
• $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
• $7,432 ($1,062/night)

]]> https://www.redweek.com/posting/R1455722 Wed, 15 Apr 2026 10:06:26 -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

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 - West Village

Kissimmee, Florida

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,440 ($206/night)

]]> https://www.redweek.com/posting/R1468474 Tue, 05 May 2026 07:08:56 -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
• $1,440 ($206/night)

]]> https://www.redweek.com/posting/R1444174 Fri, 13 Mar 2026 09:25:29 -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
• $1,878 ($268/night)

]]> https://www.redweek.com/posting/R1465361 Thu, 30 Apr 2026 10:39:24 -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
• $2,042 ($292/night)

]]> https://www.redweek.com/posting/R1451393 Tue, 14 Apr 2026 08:11:12 -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

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1469100 Tue, 05 May 2026 05:20:09 -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 - 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 - River Island

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,886 ($412/night)

]]> https://www.redweek.com/posting/R1458584 Fri, 17 Apr 2026 11:19:27 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,110 ($159/night)

]]> https://www.redweek.com/posting/R1464977 Wed, 29 Apr 2026 08:18:59 -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 - East Village

Kissimmee, Florida

• Dec 20–27, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $3,069 ($438/night)

]]> https://www.redweek.com/posting/R1468074 Sat, 02 May 2026 07:59:09 -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

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

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Dec 22, 2026 – Jan 3, 2027 (12 nights)
• 2 bed/2 bath, sleeps 8
• $3,256 ($271/night)

]]> https://www.redweek.com/posting/R1450734 Tue, 14 Apr 2026 06:02:15 -0700 Verified & Protected

WorldMark Orlando – Reunion

Kissimmee, Florida

• Dec 23–30, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1419507 Mon, 16 Feb 2026 10:26:38 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,987 ($284/night)

]]> https://www.redweek.com/posting/R1467704 Fri, 01 May 2026 15:33:16 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 25, 2026 – Jan 1, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,404 ($486/night)

]]> https://www.redweek.com/posting/R1446407 Fri, 03 Apr 2026 18:18:32 -0700 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• Dec 25, 2026 – Jan 1, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,932 ($276/night)

]]> https://www.redweek.com/posting/R1466242 Tue, 05 May 2026 07:03:55 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $866 ($124/night)

]]> https://www.redweek.com/posting/R1451111 Wed, 25 Mar 2026 07:22:14 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 26, 2026 – Jan 1, 2027 (6 nights)
• 2 bed/2 bath, sleeps 8
• $986 ($164/night)

]]> https://www.redweek.com/posting/R1455655 Thu, 02 Apr 2026 09:41:50 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,560 ($937/night)

]]> https://www.redweek.com/posting/R1455740 Wed, 15 Apr 2026 10:01:34 -0700