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 Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 13–17, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,196 ($549/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–19, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–19, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,475 ($246/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–19, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,795 ($299/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–19, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,475 ($246/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–19, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,795 ($299/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 13–17, 2027 (4 nights)
- 3 bed/3 bath, sleeps 10
- $3,513 ($878/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,458 ($780/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,568 ($261/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 14–20, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,674 ($612/night)
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Club Wyndham Clearwater Beach Resort
Clearwater, Florida- Jan 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,549 ($387/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–20, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $826 ($138/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–21, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 14–20, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,367/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Plantation Beach Club at South Seas Island Resort
Captiva, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 15–29, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,343 ($96/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 15–29, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,706 ($193/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,471 ($412/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 15–29, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,159 ($226/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,759 ($552/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–27, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($193/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,374 ($98/night)
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Club Wyndham Royal Vista
Pompano Beach, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–27, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,493 ($227/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–27, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,061 ($96/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)