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- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $830 ($208/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $706 ($176/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $937 ($234/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–20, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($184/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–19, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,012 ($127/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–19, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,436 ($179/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–19, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,943 ($243/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–20, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,275 ($253/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–20, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,185 ($132/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,053 ($579/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,462 ($176/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,198 ($171/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,699 ($121/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,247 ($232/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,112 ($222/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,397 ($171/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,586 ($370/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($432/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,042 ($292/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $499 ($166/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,476 ($211/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,605 ($321/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)