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 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–20, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $826 ($138/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,568 ($261/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,504 ($250/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,711 ($194/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,856 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 19–24, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($144/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 19–24, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,370 ($274/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 19–24, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,048 ($210/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 19–26, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,354 ($193/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $923 ($132/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,749 ($250/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($200/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $799 ($160/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($107/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,568 ($261/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 2–8, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $826 ($138/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 4–13, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,397 ($266/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 4–13, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,273 ($141/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 4–13, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,830 ($203/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($260/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–20, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,894 ($207/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,392 ($199/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $968 ($138/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–20, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,857 ($276/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–20, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,057 ($147/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,260 ($210/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 8–14, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $897 ($149/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)