Christmas Timeshare Rentals in Kissimmee
Celebrated each year on December 25, Christmas is the time for family traditions and festive travel. With schools and many businesses closed between Christmas Eve and New Year's Day, the holiday season is perfect for a getaway - whether you're dreaming of a snowy winter wonderland at a ski resort or a sunny beach Christmas with your loved ones!
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($350/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $932 ($120/night)
Club Wyndham Reunion
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $3,840 ($500/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,619 ($471/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($150/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($400/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($500/night)
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($500/night)
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($500/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $971 ($125/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,234 ($159/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($200/night)
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 ($200/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,358 ($175/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $405 ($50/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,704 ($220/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,165 ($150/night)
Silver Lake Resort
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($250/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($250/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,123 ($275/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,886 ($375/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,619 ($340/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $971 ($125/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($325/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($350/night)
Mystic Dunes Resort & Golf Club
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,002 ($129/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,104 ($199/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,323 ($199/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,434 ($185/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 10
- $1,550 ($200/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 22–27, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($240/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,465 ($189/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,465 ($189/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,352 ($305/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,319 ($170/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,512 ($195/night)
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,467 ($320/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($250/night)
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,085 ($270/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 3 bed/3 bath, sleeps 12
- $2,150 ($325/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,627 ($245/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($250/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,510 ($285/night)
Westgate Town Center
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($120/night)
Silver Lake Resort
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($275/night)