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- Feb 20–28, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,144 ($268/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 2, 2027 (10 nights)
- 3 bed/2 bath, sleeps 10
- $3,897 ($390/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 2, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,109 ($211/night)
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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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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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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 20–23, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,997 ($666/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 BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,459 ($637/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,125 ($625/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Feb 20–24, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,063 ($516/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–27, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($322/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($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
- $5,709 ($816/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($502/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $959 ($320/night)
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Hyatt Beach House Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,198 ($399/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 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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Hyatt Windward Pointe Resort
Key West, Florida- Feb 21 – Mar 6, 2027 (13 nights)
- 2 bed/2 bath, sleeps 6
- $6,543 ($503/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–27, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,180 ($197/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–28, 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 21–25, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $959 ($240/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 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($441/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,594 ($319/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($502/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,791 ($597/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,198 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–27, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $2,153 ($359/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Feb 21–23, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $1,039 ($519/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–28, 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 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,277 ($319/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
- $7,110 ($1,016/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Feb 21–23, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $852 ($426/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 22 – Mar 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 22 – Mar 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,694 ($813/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 22 – Mar 1, 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 22 – Mar 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)