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- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,229 ($205/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($221/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
- $932 ($186/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)
Verified & Protected
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)
- 1 bed/1 bath, sleeps 4
- $427 ($85/night)
Verified & Protected
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- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,310 ($210/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–8, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $897 ($224/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–8, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($131/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–8, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($246/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–8, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–8, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $395 ($99/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,549 ($232/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,356 ($123/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $1,996 ($181/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $968 ($88/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)
- 2 bed/2 bath, sleeps 8
- $1,083 ($181/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 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,251 ($208/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($87/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,074 ($215/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,061 ($96/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,449 ($132/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,493 ($227/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,733 ($248/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($193/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $459 ($92/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 7–14, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 7–14, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $591 ($84/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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
- $1,932 ($276/night)