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- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,321 ($332/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $3,404 ($681/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,976 ($854/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,275 ($379/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
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Marriott's Harbour Lake
Orlando, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($253/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,594 ($531/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($322/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 3–5, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,139 ($569/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,232 ($446/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $1,996 ($181/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,356 ($123/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,310 ($210/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $968 ($88/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 4–15, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,549 ($232/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,966 ($852/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($87/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($122/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 5–11, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,026 ($338/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jan 5–9, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,251 ($208/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,383 ($230/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,083 ($181/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 5–11, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,895 ($316/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–13, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,967 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,276 ($255/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $2,730 ($248/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–12, 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 6–12, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,861 ($310/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 6–12, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,565 ($1,094/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $3,402 ($309/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 6
- $3,321 ($302/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,830 ($166/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,449 ($132/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,493 ($227/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,733 ($248/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($193/night)