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.
Westgate Vacation Villas
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,314 ($331/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,123 ($303/night)
Vacation Village at Parkway
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (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 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 9, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,825 ($273/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,001 ($286/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,123 ($303/night)
Silver Lake Resort
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,161 ($309/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($330/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,619 ($231/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Silver Lake Resort
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,465 ($209/night)
Silver Lake Resort
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,396 ($199/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,161 ($309/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,238 ($320/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,476 ($211/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (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 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Westgate Town Center
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (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 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,495 ($249/night)
Westgate Vacation Villas
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,749 ($250/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–9, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($246/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–9, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–9, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($131/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,083 ($181/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 10–16, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($122/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,383 ($230/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($131/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($246/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
Vacation Village at Parkway
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,542 ($220/night)
Westgate Vacation Villas
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,306 ($329/night)
Westgate Town Center
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,563 ($223/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,742 ($249/night)
Westgate Vacation Villas
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,358 ($194/night)