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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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,843 ($549/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,201 ($534/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,661 ($443/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,233 ($647/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
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The Galleon Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,655 ($1,094/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,126 ($447/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,590 ($265/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,590 ($265/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,180 ($197/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,654 ($1,093/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,891 ($984/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,839 ($368/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,352 ($270/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,586 ($370/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–24, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,114 ($279/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–24, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,524 ($381/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–24, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,114 ($279/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–24, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $826 ($206/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,352 ($270/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,978 ($283/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,711 ($387/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,891 ($984/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,366 ($296/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($220/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 3 bed/2 bath, sleeps 10
- $3,269 ($409/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,366 ($296/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21 – Mar 7, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,932 ($281/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,998 ($800/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $3,262 ($652/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Feb 21–22, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $523 ($523/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 21–27, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,177 ($363/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $888 ($178/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)