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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Sheraton Vistana Resort
Orlando, Florida- Dec 22–30, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $999 ($125/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,699 ($1,528/night)
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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)
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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)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23, 2026 – Jan 4, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $3,561 ($297/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23, 2026 – Jan 4, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,900 ($158/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23, 2026 – Jan 4, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,734 ($145/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23, 2026 – Jan 4, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($109/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23, 2026 – Jan 4, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,702 ($225/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23, 2026 – Jan 4, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $3,025 ($252/night)
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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)
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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
- $1,764 ($196/night)
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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)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $3,077 ($769/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–27, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,383 ($346/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($236/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–27, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $737 ($184/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–27, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($249/night)
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WorldMark Orlando – Reunion
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,641 ($377/night)
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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)
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Hilton Grand Vacations at Tuscany Village
Orlando, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $3,534 ($883/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,519 ($217/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($303/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23–28, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($149/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,141 ($228/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,699 ($243/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,312 ($262/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 23–28, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $568 ($114/night)
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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)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–28, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $870 ($174/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 23–31, 2026 (8 nights)
- Studio/1 bath, sleeps 5
- $8,118 ($1,015/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($326/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 23–29, 2026 (6 nights)
- Studio/1 bath, sleeps 5
- $4,930 ($822/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,107 ($158/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,134 ($591/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,759 ($1,966/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $527 ($176/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $790 ($263/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 24–26, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,123 ($562/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–29, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $870 ($174/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($326/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($236/night)