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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,723 ($1,246/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,260 ($323/night)
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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
- $3,186 ($455/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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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
- $1,476 ($211/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 4, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($184/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,532 ($255/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $937 ($187/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
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Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- Studio/1 bath, sleeps 3
- $2,750 ($550/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,295 ($259/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/night)
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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)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,980 ($283/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 4, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,687 ($281/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,251 ($179/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,450 ($290/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,976 ($795/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 5, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,745 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 5, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,074 ($179/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($202/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,154 ($288/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $941 ($188/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $582 ($194/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $817 ($272/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $2,238 ($746/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($662/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,707 ($1,530/night)
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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)
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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)
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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)
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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)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $2,111 ($704/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,627 ($542/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,826 ($609/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,439 ($688/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 2, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,509 ($755/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 6, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,585 ($431/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,374 ($344/night)