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 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $919 ($131/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,756 ($251/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,290 ($184/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–18, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,199 ($229/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–18, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,406 ($172/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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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 4–18, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–9, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–9, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 6–9, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $499 ($166/night)
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Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Vacation Village at Parkway
Kissimmee, Florida- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–21, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $946 ($189/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–21, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $679 ($136/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–22, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,079 ($180/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–22, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,462 ($244/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–21, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,312 ($262/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–22, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($127/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–21, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,163 ($291/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–21, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $599 ($150/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 17–21, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $813 ($203/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
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–26, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,943 ($243/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 18–27, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,185 ($132/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–27, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($184/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–27, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,275 ($253/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,012 ($127/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 18–26, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,436 ($179/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
- $3,077 ($440/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 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/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
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/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
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/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
- $2,423 ($346/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)