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 Cypress Palms
Kissimmee, Florida- Jan 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($193/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 6–17, 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 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
- $1,074 ($215/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 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/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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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 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 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 6–13, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/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
- $2,651 ($530/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 6–12, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,795 ($299/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 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $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
- $2,492 ($498/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 6–11, 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 7–16, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $2,680 ($298/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,680 ($298/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
- $719 ($180/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $2,202 ($245/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–13, 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 7–11, 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 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,304 ($326/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,777 ($309/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)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–13, 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 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,271 ($318/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–13, 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 7–13, 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 7–13, 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 7–16, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,475 ($164/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 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 8–13, 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 8–13, 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 8–13, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,276 ($255/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 8–11, 2027 (3 nights)
- 3 bed/3 bath, sleeps 10
- $3,622 ($1,207/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $935 ($312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,638 ($806/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($166/night)