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
Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,276 ($325/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,629 ($204/night)
Verified & Protected
Hilton Grand Vacations at SeaWorld
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,745 ($392/night)
Verified & Protected
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
Marriott's Royal Palms
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,290 ($470/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,542 ($220/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,405 ($201/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,922 ($275/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,590 ($265/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,253 ($282/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
Verified & Protected
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,891 ($270/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–31, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,352 ($270/night)
Verified & Protected
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 26–28, 2026 (2 nights)
- Studio/1 bath, sleeps 5
- $1,495 ($748/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,180 ($197/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
Verified & Protected
Marriott's Imperial Palm Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $4,112 ($588/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($164/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 26–29, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $2,100 ($700/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($330/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 4, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,546 ($283/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 4, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($196/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,800 ($800/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,380 ($626/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
Verified & Protected
Marriott's Royal Palms
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–29, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $648 ($216/night)
Verified & Protected
Marriott's Sabal Palms
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,262 ($466/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
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
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 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
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
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
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
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
- $5,473 ($782/night)