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.
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $768 ($154/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–27, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($167/night)
Marriott's Harbour Lake
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
Las Palmeras by Hilton Grand Vacations
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 4
- $2,772 ($396/night)
Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,802 ($543/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,522 ($304/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Silver Lake Resort
Kissimmee, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 22, 2026 – Jan 3, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,929 ($244/night)
Holiday Inn Club Vacations Orlando Breeze Resort
Davenport, Florida- Dec 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,020 ($860/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 22–28, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,478 ($413/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($278/night)
Hilton Grand Vacations at Tuscany Village
Orlando, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,856 ($265/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 22–26, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $844 ($211/night)
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 22–26, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($824/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 22–26, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,054 ($264/night)
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 22–27, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,512 ($216/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($284/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–27, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $737 ($184/night)
Hilton Grand Vacations at SeaWorld
Orlando, Florida- Dec 23, 2026 – Jan 2, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($275/night)
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $3,077 ($769/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 23, 2026 – Jan 1, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,781 ($198/night)
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 23–28, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,568 ($714/night)
Hilton Grand Vacations at SeaWorld
Orlando, Florida- Dec 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,385 ($277/night)
WorldMark Orlando – Reunion
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,641 ($377/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,660 ($415/night)
Mystic Dunes Resort & Golf Club
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,311 ($187/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($388/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–26, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $507 ($169/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $999 ($250/night)
Hilton Grand Vacations at Tuscany Village
Orlando, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,489 ($641/night)
Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Dec 23–26, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,830 ($610/night)
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 23–31, 2026 (8 nights)
- Studio/1 bath, sleeps 5
- $8,118 ($1,015/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $604 ($201/night)
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 24–25, 2026 (1 night)
- Studio/1 bath, sleeps 4
- $517 ($517/night)
Marriott's Royal Palms
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($553/night)
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 24–26, 2026 (2 nights)
- Studio/1 bath, sleeps 5
- $3,108 ($1,554/night)
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 24–25, 2026 (1 night)
- Studio/1 bath, sleeps 4
- $606 ($606/night)
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $2,804 ($935/night)
Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,238 ($320/night)
Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $3,347 ($1,116/night)