Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,022 ($289/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–20, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $551 ($184/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,370 ($171/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($249/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,076 ($297/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($236/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,107 ($158/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,383 ($346/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($326/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/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
- $6,892 ($985/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,198 ($171/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,136 ($162/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–22, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $507 ($169/night)
Westgate Town Center
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,381 ($197/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 ($314/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
- $3,077 ($440/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 ($209/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–23, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $627 ($157/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
- $1,330 ($190/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
- $1,319 ($188/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,513 ($502/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–25, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,169 ($292/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,123 ($303/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $1,242 ($177/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 ($276/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 ($166/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $684 ($228/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $855 ($214/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 ($385/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–27, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,336 ($167/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 ($276/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 ($374/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
- $2,968 ($424/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
- $2,161 ($309/night)
Silver Lake Resort
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/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
- $2,750 ($393/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
- $1,396 ($199/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
- $2,306 ($329/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
- $2,306 ($329/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
- $2,042 ($292/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,986 ($284/night)