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 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,488 ($248/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–20, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $790 ($132/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–17, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $415 ($138/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,830 ($261/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–19, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $710 ($178/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–19, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $897 ($224/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,392 ($199/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $977 ($140/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–19, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $483 ($121/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–18, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–18, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $463 ($154/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 15–18, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $415 ($138/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,926 ($275/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,030 ($147/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,444 ($206/night)
Marriott's Grande Vista
Orlando, Florida- Dec 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–22, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $817 ($163/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,022 ($289/night)
Hilton Grand Vacations at SeaWorld
Orlando, Florida- Dec 17–20, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $583 ($194/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,128 ($226/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,497 ($214/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–20, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $755 ($252/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,083 ($155/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–20, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,039 ($346/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–23, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,778 ($296/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–20, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $551 ($184/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–23, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,312 ($219/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–21, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($235/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,532 ($306/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–21, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,286 ($322/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–23, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $950 ($158/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–21, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($171/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,107 ($158/night)
WorldMark Orlando Kingstown Reef
Orlando, Florida- Dec 18–21, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,165 ($388/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,076 ($297/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,383 ($346/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 18–22, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,765 ($441/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,473 ($210/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($249/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,370 ($171/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 18–22, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,765 ($441/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($236/night)
Aqua Sol, a Hilton Vacation Club
Winter Garden, Greater Orlando, Florida- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($277/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($326/night)