https://www.redweek.com/featured/spring-summer-rentals/North+America/United+States/Florida/Kissimmee?sort=date en Fri, 10 Apr 2026 09:59:38 -0700 3600 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• Apr 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 10
• $2,804 ($401/night)

]]> https://www.redweek.com/posting/R1419369 Sat, 17 Jan 2026 11:43:04 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• Apr 23–30, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1444169 Fri, 13 Mar 2026 09:23:59 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Apr 24 – May 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($190/night)

]]> https://www.redweek.com/posting/R1451407 Mon, 30 Mar 2026 06:54:20 -0700 Verified & Protected

Club Wyndham Reunion

Kissimmee, Florida

• Apr 25 – May 2, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1444693 Wed, 01 Apr 2026 09:09:19 -0700 Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

• Apr 26 – May 3, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,462 ($209/night)

]]> https://www.redweek.com/posting/R1442924 Fri, 13 Mar 2026 07:49:29 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• Apr 26 – May 10, 2026 (14 nights)
• 2 bed/2 bath, sleeps 8
• $3,062 ($219/night)

]]> https://www.redweek.com/posting/R1442061 Wed, 25 Mar 2026 08:32:24 -0700 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

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $583 ($83/night)

]]> https://www.redweek.com/posting/R1415570 Wed, 28 Jan 2026 13:04:52 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $777 ($111/night)

]]> https://www.redweek.com/posting/R1427008 Wed, 18 Feb 2026 13:24:26 -0800 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

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $583 ($83/night)

]]> https://www.redweek.com/posting/R1417601 Wed, 28 Jan 2026 13:04:36 -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
• $1,088 ($155/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 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

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

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/R1415576 Wed, 28 Jan 2026 13:05:14 -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
• $777 ($111/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

Club Wyndham Cypress Palms

Kissimmee, Florida

• May 10–14, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $503 ($126/night)

]]> https://www.redweek.com/posting/R1452403 Thu, 26 Mar 2026 14:45:44 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• May 12–15, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $336 ($112/night)

]]> https://www.redweek.com/posting/R1447804 Tue, 17 Mar 2026 12:49:43 -0700 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

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

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

Club Wyndham Cypress Palms

Kissimmee, Florida

• May 16–20, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $414 ($104/night)

]]> https://www.redweek.com/posting/R1447893 Tue, 17 Mar 2026 14:47:31 -0700 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

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 18–21, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $243 ($81/night)

]]> https://www.redweek.com/posting/R1448617 Thu, 19 Mar 2026 06:31:05 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

• May 22–29, 2026 (7 nights)
• 3 bed/3 bath, sleeps 11
• $1,660 ($237/night)

]]> https://www.redweek.com/posting/R1316168 Tue, 11 Nov 2025 21:14:37 -0800 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
• $887 ($296/night)

]]> https://www.redweek.com/posting/R1421444 Thu, 29 Jan 2026 08:30:05 -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 - West Village

Kissimmee, Florida

• May 22–26, 2026 (4 nights)
• 3 bed/3 bath, sleeps 12
• $1,054 ($264/night)

]]> https://www.redweek.com/posting/R1411017 Wed, 14 Jan 2026 15:40:09 -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
• $1,329 ($190/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 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($190/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

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 Wed, 08 Apr 2026 15:37:12 -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 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• May 25–30, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $601 ($120/night)

]]> https://www.redweek.com/posting/R1447706 Tue, 17 Mar 2026 11:00:37 -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
• $1,654 ($236/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 - West Village

Kissimmee, Florida

• May 31 – Jun 5, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $505 ($101/night)

]]> https://www.redweek.com/posting/R1439118 Wed, 18 Mar 2026 14:09:35 -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 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 1–5, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $305 ($76/night)

]]> https://www.redweek.com/posting/R1456733 Sat, 04 Apr 2026 13:54:50 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Jun 1–7, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $539 ($90/night)

]]> https://www.redweek.com/posting/R1453033 Fri, 27 Mar 2026 12:19:09 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Jun 1–8, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $667 ($95/night)

]]> https://www.redweek.com/posting/R1447809 Tue, 17 Mar 2026 12:54:03 -0700