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 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 6–17, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,061 ($96/night)
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Club Wyndham National Harbor
National Harbor, Maryland- Jan 6–10, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,778 ($444/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)
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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
- $2,493 ($227/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 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 6–17, 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 6–17, 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 6–17, 2027 (11 nights)
- 2 bed/2 bath, sleeps 6
- $3,321 ($302/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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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 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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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 6–11, 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 6–11, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/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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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 6–10, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,100 ($525/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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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 6–10, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,188 ($547/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 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 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)
- 2 bed/2 bath, sleeps 6
- $1,550 ($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
- $986 ($164/night)
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Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,091 ($1,156/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 6
- $1,795 ($299/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 7–13, 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 7–16, 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 7–11, 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)
- 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)
- 3 bed/2 bath, sleeps 10
- $2,680 ($298/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 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 7–13, 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 7–13, 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 7–16, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,475 ($164/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,218 ($1,031/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 7–12, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)