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 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–14, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $424 ($141/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
- $719 ($180/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)
Sheraton Vistana Resort
Orlando, 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
- $759 ($152/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 8
- $4,603 ($658/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 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,202 ($172/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)
- 2 bed/2 bath, sleeps 8
- $1,532 ($219/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,512 ($216/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,092 ($182/night)
Vacation Village at Parkway
Kissimmee, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $971 ($139/night)
The Houses at Summer Bay Orlando
Clermont, Florida- Dec 13–20, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,314 ($331/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)
- 2 bed/2 bath, sleeps 8
- $1,286 ($184/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,231 ($205/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $870 ($124/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,434 ($205/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–18, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($83/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,638 ($234/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)
- 2 bed/2 bath, sleeps 8
- $1,198 ($200/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–18, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $755 ($151/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–18, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $666 ($133/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($163/night)
Marriott's Grande Vista
Orlando, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Marriott's Grande Vista
Orlando, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–18, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $604 ($151/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 14–17, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,734 ($248/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–18, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($134/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $924 ($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 14–18, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $343 ($86/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,488 ($248/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–17, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,339 ($191/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–17, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $463 ($154/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)
- 2 bed/2 bath, sleeps 8
- $1,154 ($192/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,048 ($210/night)