Winter Rentals
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 14–21, 2025 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,550 ($221/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 14–21, 2025 (7 nights)
- 4 bed/4 bath, sleeps 16
- $666 ($95/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $552 ($79/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 14–21, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($377/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($248/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($248/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,527 ($218/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–22, 2025 (3 nights)
- 2 bed/2 bath, sleeps 8
- $502 ($167/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,088 ($155/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($198/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,687 ($241/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($315/night)
Verified & Protected
Hilton Vacation Club Aqua Sol Orlando West
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 3 bed/3 bath, sleeps 10
- $1,932 ($276/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,166 ($167/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/1.5 bath, sleeps 8
- $1,220 ($174/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($159/night)
Verified & Protected
Hilton Vacation Club Aqua Sol Orlando West
Kissimmee, Florida- Dec 20–24, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $666 ($166/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $555 ($79/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,434 ($205/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,088 ($155/night)
Verified & Protected
Vacation Village at Parkway
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $666 ($95/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $955 ($136/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,286 ($184/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,586 ($370/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
Verified & Protected
Vacation Villas at Fantasy World
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–26, 2025 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,264 ($211/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($253/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,878 ($268/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,286 ($184/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,286 ($184/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
WorldMark Orlando – Reunion
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,987 ($284/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
Verified & Protected
Westgate Towers
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,320 ($189/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($143/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($143/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,749 ($393/night)
Verified & Protected
Silver Lake Resort
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
Verified & Protected
Vacation Village at Parkway
Kissimmee, Florida- Dec 21, 2025 – Jan 4, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($173/night)
Verified & Protected
Vacation Villas at Fantasy World
Kissimmee, Florida- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($190/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 21–26, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $855 ($171/night)