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.
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20, 2026 – Jan 1, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,795 ($150/night)
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Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,390 ($341/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,497 ($500/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,107 ($158/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20, 2026 – Jan 1, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,467 ($206/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20, 2026 – Jan 1, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $3,339 ($278/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,586 ($370/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($346/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 9
- $6,782 ($969/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
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Marriott's Harbour Lake
Orlando, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($404/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Dec 20–22, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $952 ($476/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
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Parc Soleil by Hilton Grand Vacations
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,123 ($303/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,107 ($158/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,605 ($321/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21, 2026 – Jan 1, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,664 ($151/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 21–25, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $2,685 ($671/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,436 ($287/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21, 2026 – Jan 1, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,283 ($208/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $768 ($154/night)
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Hilton Grand Vacations at SeaWorld
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,519 ($217/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,076 ($297/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,057 ($211/night)
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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)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21, 2026 – Jan 1, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $3,094 ($281/night)
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Silver Lake Resort
Kissimmee, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 22, 2026 – Jan 2, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,730 ($157/night)
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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)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 22–30, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,268 ($159/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 22–30, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,734 ($217/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 22, 2026 – Jan 2, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($294/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
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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
- $3,256 ($271/night)
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Hilton Grand Vacations at Tuscany Village
Orlando, Florida- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,204 ($315/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 22–30, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,362 ($295/night)