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 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,013 ($288/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,497 ($214/night)
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Hyatt Beach House Resort
Key West, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Marriott's Grande Vista
Orlando, Florida- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,220 ($244/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Feb 14–19, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,129 ($626/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 14–16, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $1,244 ($622/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,565 ($652/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,222 ($460/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,074 ($154/night)
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Westgate Vacation Villas
Kissimmee, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,378 ($340/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,347 ($907/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–18, 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 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Marriott's Harbour Lake
Orlando, Florida- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($222/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–20, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $2,153 ($359/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–17, 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 14–17, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $959 ($320/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–20, 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 14–21, 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 14–17, 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 14–18, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,277 ($319/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,879 ($411/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,590 ($265/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,302 ($615/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–19, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,277 ($319/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–19, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $959 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–25, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,996 ($200/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–19, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 15–20, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($550/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–25, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,685 ($268/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,840 ($263/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–25, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,685 ($268/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,341 ($557/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–20, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–20, 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 15–25, 2027 (10 nights)
- 3 bed/2 bath, sleeps 10
- $3,653 ($365/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–20, 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 15–20, 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 15–19, 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 17–24, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,711 ($387/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Feb 17–21, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $3,687 ($922/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 17–22, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,506 ($301/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 17–27, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,837 ($284/night)
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Daytona Beach Regency
Daytona Beach, Florida- Feb 17–22, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,220 ($244/night)