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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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,734 ($248/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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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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 4–8, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($660/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 5–11, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,083 ($181/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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/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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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 Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–10, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,077 ($269/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $459 ($92/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 6–11, 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 6–12, 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 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–12, 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 6–13, 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 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,830 ($166/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–13, 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 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 6–10, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,304 ($326/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,074 ($215/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,996 ($599/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–17, 2027 (11 nights)
- 3 bed/2 bath, sleeps 10
- $3,321 ($302/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/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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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 6–10, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,271 ($318/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 9
- $9,276 ($1,855/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 Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/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 6–10, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,304 ($326/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
- $852 ($170/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/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
- $2,651 ($530/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,466 ($693/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–13, 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 6–10, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($180/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
- $2,492 ($498/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 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–11, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/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
- $986 ($164/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 6
- $1,550 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–11, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,077 ($269/night)