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.
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 11–15, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($131/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($246/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($160/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $799 ($200/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($110/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–13, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,794 ($233/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–13, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,488 ($124/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–13, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,179 ($182/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($246/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 7–11, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($131/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,563 ($223/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,840 ($263/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 25, 2027 – Jan 1, 2028 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,660 ($237/night)