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.
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 29, 2026 – Jan 4, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $653 ($109/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,088 ($218/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $870 ($174/night)
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Westgate Vacation Villas
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,467 ($176/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($120/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $591 ($84/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,138 ($224/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($246/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 11–15, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($131/night)
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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- Jan 12–16, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($160/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $799 ($200/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,268 ($181/night)
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Westgate Vacation Villas
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($233/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,035 ($148/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,926 ($275/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–22, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,839 ($204/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–22, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($146/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–22, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,454 ($273/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,497 ($214/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,013 ($288/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,074 ($154/night)
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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)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)