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- Feb 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)
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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
- $1,260 ($210/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,974 ($282/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,471 ($210/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,057 ($151/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–18, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,524 ($218/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–18, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($159/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–18, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,070 ($296/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–17, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,826 ($304/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–17, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,339 ($223/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($334/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $968 ($242/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–17, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $977 ($163/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 11–15, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–18, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,874 ($312/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–18, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($228/night)
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Westgate Town Center
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,563 ($223/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–15, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,136 ($379/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–15, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $604 ($201/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–18, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($167/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–15, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $808 ($269/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–19, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,046 ($292/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–19, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $901 ($150/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–19, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($207/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,092 ($156/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,512 ($216/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–27, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,563 ($197/night)
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Westgate Vacation Villas
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,001 ($286/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,066 ($152/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)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,004 ($286/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–27, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $1,791 ($138/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–27, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $3,365 ($259/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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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $932 ($186/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($248/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 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($141/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,861 ($266/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,418 ($203/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)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–28, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,647 ($206/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–28, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,132 ($142/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–28, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,144 ($268/night)