https://www.redweek.com/featured/spring-summer-rentals/North+America/United+States/Florida/Kissimmee?sort=date en Sun, 19 Apr 2026 15:38:21 -0700 3600 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 1–8, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1355411 Wed, 29 Oct 2025 11:35:30 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,742 ($249/night)

]]> https://www.redweek.com/posting/R1436191 Wed, 04 Mar 2026 13:24:16 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $555 ($79/night)

]]> https://www.redweek.com/posting/R1419347 Wed, 18 Feb 2026 14:19:57 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $660 ($94/night)

]]> https://www.redweek.com/posting/R1391822 Mon, 08 Dec 2025 12:55:48 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $583 ($83/night)

]]> https://www.redweek.com/posting/R1427025 Wed, 18 Feb 2026 13:24:17 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $583 ($83/night)

]]> https://www.redweek.com/posting/R1415576 Wed, 28 Jan 2026 13:05:14 -0800 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,473 ($210/night)

]]> https://www.redweek.com/posting/R1436292 Tue, 24 Feb 2026 13:21:18 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $583 ($83/night)

]]> https://www.redweek.com/posting/R1427043 Wed, 18 Feb 2026 13:54:24 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 8–15, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1357807 Tue, 04 Nov 2025 12:31:55 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1365506 Wed, 12 Nov 2025 09:19:03 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,204 ($315/night)

]]> https://www.redweek.com/posting/R1397255 Thu, 18 Dec 2025 08:31:10 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,165 ($166/night)

]]> https://www.redweek.com/posting/R1402829 Fri, 19 Dec 2025 10:03:12 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1416468 Wed, 04 Feb 2026 10:08:08 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1447945 Tue, 24 Mar 2026 14:13:35 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 17–24, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1368183 Fri, 14 Nov 2025 14:31:12 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• May 22–27, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $666 ($133/night)

]]> https://www.redweek.com/posting/R1450162 Tue, 07 Apr 2026 10:43:49 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• May 22–25, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $998 ($333/night)

]]> https://www.redweek.com/posting/R1421444 Thu, 29 Jan 2026 08:30:05 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• May 22–29, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $665 ($95/night)

]]> https://www.redweek.com/posting/R1348912 Tue, 11 Nov 2025 21:14:37 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 22–26, 2026 (4 nights)
• 3 bed/3 bath, sleeps 12
• $888 ($222/night)

]]> https://www.redweek.com/posting/R1411017 Wed, 14 Jan 2026 15:40:09 -0800 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,714 ($245/night)

]]> https://www.redweek.com/posting/R1432729 Wed, 15 Apr 2026 12:17:35 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,220 ($174/night)

]]> https://www.redweek.com/posting/R1420903 Wed, 04 Feb 2026 10:15:43 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 23–30, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $1,660 ($237/night)

]]> https://www.redweek.com/posting/R1326858 Fri, 22 Aug 2025 08:46:55 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,532 ($362/night)

]]> https://www.redweek.com/posting/R1421299 Wed, 04 Feb 2026 13:35:34 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• May 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $944 ($135/night)

]]> https://www.redweek.com/posting/R1458556 Fri, 17 Apr 2026 16:16:09 -0700 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1412401 Mon, 02 Feb 2026 12:41:54 -0800

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• May 25–29, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $1,109 ($277/night)

]]> https://www.redweek.com/posting/R1459794 Sat, 11 Apr 2026 12:20:29 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 29 – Jun 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,536 ($219/night)

]]> https://www.redweek.com/posting/R1402486 Tue, 09 Dec 2025 09:14:35 -0800 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• May 29 – Jun 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,434 ($205/night)

]]> https://www.redweek.com/posting/R1450822 Fri, 03 Apr 2026 13:00:37 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 30 – Jun 6, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,440 ($206/night)

]]> https://www.redweek.com/posting/R1441512 Wed, 18 Mar 2026 12:48:55 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1462152 Fri, 17 Apr 2026 08:48:54 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1462158 Fri, 17 Apr 2026 08:52:19 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,536 ($219/night)

]]> https://www.redweek.com/posting/R1358162 Wed, 05 Nov 2025 10:32:41 -0800

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1462591 Sat, 18 Apr 2026 08:21:50 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• May 31 – Jun 7, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $2,157 ($308/night)

]]> https://www.redweek.com/posting/R1416975 Fri, 30 Jan 2026 12:00:23 -0800 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Jun 3–6, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $297 ($99/night)

]]> https://www.redweek.com/posting/R1457561 Mon, 06 Apr 2026 18:12:05 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• Jun 3–8, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $1,385 ($277/night)

]]> https://www.redweek.com/posting/R1425116 Mon, 09 Feb 2026 14:13:55 -0800 Verified & Protected

WorldMark Orlando – Reunion

Kissimmee, Florida

• Jun 4–11, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $3,382 ($483/night)

]]> https://www.redweek.com/posting/R1320323 Tue, 11 Nov 2025 21:14:37 -0800 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• Jun 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,434 ($205/night)

]]> https://www.redweek.com/posting/R1460975 Fri, 17 Apr 2026 14:45:50 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Jun 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,009 ($287/night)

]]> https://www.redweek.com/posting/R1436858 Mon, 16 Mar 2026 10:05:10 -0700 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Jun 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,495 ($214/night)

]]> https://www.redweek.com/posting/R1455545 Wed, 08 Apr 2026 08:00:47 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Jun 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,660 ($237/night)

]]> https://www.redweek.com/posting/R1322002 Tue, 11 Nov 2025 21:14:37 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Jun 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($190/night)

]]> https://www.redweek.com/posting/R1408842 Thu, 15 Jan 2026 08:28:47 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• Jun 7–14, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,887 ($984/night)

]]> https://www.redweek.com/posting/R1448842 Wed, 25 Mar 2026 09:21:08 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• Jun 9–15, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $1,758 ($293/night)

]]> https://www.redweek.com/posting/R1436662 Thu, 12 Mar 2026 15:46:42 -0700

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• Jun 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1462594 Sat, 18 Apr 2026 08:27:47 -0700

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Jun 12–19, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $1,110 ($159/night)

]]> https://www.redweek.com/posting/R1462873 Sun, 19 Apr 2026 07:00:40 -0700

Westgate Vacation Villas

Kissimmee, Florida

• Jun 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $999 ($143/night)

]]> https://www.redweek.com/posting/R1434772 Tue, 17 Feb 2026 09:57:30 -0800 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• Jun 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,495 ($214/night)

]]> https://www.redweek.com/posting/R1432883 Mon, 30 Mar 2026 10:00:47 -0700