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.
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–6, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,273 ($255/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–13, 2026 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,680 ($223/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($125/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $937 ($234/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,524 ($218/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 2–10, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $879 ($110/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $799 ($114/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 2–10, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($209/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 3–7, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,026 ($256/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 3–7, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
Vacation Village at Parkway
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,033 ($148/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–7, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–7, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Westgate Town Center
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–8, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–8, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–13, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $919 ($115/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–13, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,760 ($220/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–19, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,937 ($210/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–10, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–10, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($100/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–19, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($111/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($160/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $892 ($149/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–17, 2026 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,022 ($184/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–17, 2026 (11 nights)
- 2 bed/2 bath, sleeps 8
- $1,647 ($150/night)
Vacation Village at Parkway
Kissimmee, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $971 ($139/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–17, 2026 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,066 ($97/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $573 ($95/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,092 ($182/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Silver Lake Resort
Kissimmee, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,444 ($206/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–12, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $759 ($152/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–11, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $604 ($151/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–12, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,127 ($161/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–12, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($100/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–11, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $343 ($86/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $755 ($108/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 7–11, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($134/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $755 ($108/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $626 ($157/night)