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 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,524 ($218/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,202 ($172/night)
Verified & Protected
Marriott's Harbour Lake
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($386/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
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $626 ($157/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($191/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,198 ($240/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–30, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–30, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
Verified & Protected
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,529 ($218/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($550/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,114 ($186/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,865 ($266/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 BoardWalk Villas
Lake Buena Vista, Florida- Dec 27–31, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $3,478 ($870/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 Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $888 ($178/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,532 ($255/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 4, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($184/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $790 ($198/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 10, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,440 ($174/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–31, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27–31, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,043 ($174/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($221/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)
- 3 bed/3 bath, sleeps 12
- $4,112 ($588/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 4, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,158 ($270/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
Sheraton Vistana Villages
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 10, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,993 ($285/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 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $990 ($198/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,356 ($113/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($105/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($105/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($105/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $817 ($163/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,163 ($194/night)