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
Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,952 ($422/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,625 ($271/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,066 ($152/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $932 ($186/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,688 ($670/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $6,510 ($930/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,303 ($329/night)
Verified & Protected
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 4 bed/4 bath, sleeps 16
- $6,560 ($937/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (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 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($200/night)
Verified & Protected
Marriott's Harbour Lake
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,222 ($317/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,632 ($326/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($441/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,632 ($326/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $5,440 ($777/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,743 ($549/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 27–31, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $3,478 ($870/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,632 ($326/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,216 ($203/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $5,668 ($810/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($248/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 9
- $6,892 ($985/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,161 ($309/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,004 ($286/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $13,105 ($1,872/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,497 ($214/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($144/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,030 ($206/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($147/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $746 ($186/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,956 ($280/night)