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 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,074 ($215/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 29 – Feb 7, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,145 ($127/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 29 – Feb 7, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,157 ($240/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 29 – Feb 7, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($187/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
- $1,365 ($195/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 1–6, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($233/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 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,268 ($181/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 7–13, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,431 ($239/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 7–13, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($185/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 7–13, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($127/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 8–11, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $604 ($201/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 8–11, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $786 ($262/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,003 ($201/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 10–15, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $706 ($141/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,035 ($148/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,926 ($275/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–22, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,454 ($273/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–22, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($146/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–16, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $507 ($169/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–16, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $684 ($228/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–16, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–22, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,839 ($204/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–28, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,719 ($194/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,634 ($272/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–28, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,570 ($255/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,216 ($203/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–20, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $875 ($146/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,013 ($288/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,497 ($214/night)