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 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,043 ($174/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $799 ($114/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,202 ($172/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $463 ($154/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($105/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,048 ($171/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($104/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $990 ($198/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,387 ($198/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,136 ($162/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($105/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,554 ($213/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($105/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $817 ($163/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,585 ($198/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,295 ($162/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,356 ($113/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $415 ($138/night)
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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 29, 2026 – Jan 4, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,238 ($206/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 29, 2026 – Jan 4, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,003 ($167/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)
Verified & Protected
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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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 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,138 ($224/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 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
- $839 ($120/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 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,083 ($181/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,383 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($122/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 8–13, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 8–13, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 8–13, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/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 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)
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 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 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 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)