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 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 16–23, 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- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Coconut Beach Resort
Key West, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Marriott's Villas at Doral
Miami, Florida- Jan 16–22, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $5,793 ($966/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–30, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,734 ($195/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–30, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,175 ($227/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,734 ($248/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 16–22, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,251 ($542/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,007 ($858/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–22, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,816 ($803/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 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- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,076 ($439/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 9
- $5,910 ($844/night)
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Shell Island Beach Club
Sanibel Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,535 ($362/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,990 ($570/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,345 ($469/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–17, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $586 ($586/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,504 ($250/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,462 ($292/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,711 ($194/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,281 ($326/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,856 ($133/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,082 ($616/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,596 ($599/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,764 ($441/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,589 ($227/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,362 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $671 ($96/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 17–22, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,472 ($494/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 17–24, 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- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)