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.
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,069 ($414/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,302 ($260/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,302 ($260/night)
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,542 ($220/night)
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)
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)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,123 ($303/night)
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,772 ($396/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,657 ($380/night)
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)
Sheraton Vistana Resort
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,512 ($216/night)
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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)
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($332/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $5,748 ($821/night)
Parc Soleil by Hilton Grand Vacations
Orlando, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($277/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,165 ($388/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,682 ($420/night)
Marriott's Grande Vista
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,153 ($450/night)
Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $3,731 ($933/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($222/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,047 ($292/night)
Marriott's Grande Vista
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Las Palmeras by Hilton Grand Vacations
Orlando, Florida- Dec 29, 2026 – Jan 1, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,495 ($498/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 3, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,069 ($414/night)
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 1, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $3,132 ($1,044/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 29, 2026 – Jan 1, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $583 ($194/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 1, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,297 ($432/night)
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $3,243 ($1,081/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($662/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($332/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($443/night)
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,748 ($583/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 9, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $3,213 ($357/night)
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $4,184 ($837/night)
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,730 ($683/night)
Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,965 ($593/night)
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,743 ($549/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,336 ($260/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,712 ($542/night)
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $866 ($433/night)