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 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,444 ($206/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
- $790 ($198/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $626 ($157/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–14, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–13, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($160/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–14, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,128 ($226/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–12, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–14, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($170/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–12, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $499 ($166/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–12, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $586 ($195/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($170/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,128 ($226/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $862 ($172/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,144 ($229/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–15, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($160/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $595 ($119/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,532 ($219/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,202 ($172/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–18, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $573 ($95/night)
Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–17, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($100/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $892 ($149/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,092 ($182/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $759 ($152/night)
Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
Westgate Town Center
Kissimmee, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,696 ($242/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–19, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $635 ($106/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $870 ($124/night)