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 29 – Feb 1, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $876 ($292/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 29 – Feb 1, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($195/night)
Eagle's Nest Beach Resort
Marco Island, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 29 – Feb 2, 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 29 – Feb 5, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 29–30, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $487 ($487/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 29 – Feb 1, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $1,057 ($352/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 29 – Feb 2, 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 29 – Feb 2, 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 29 – Feb 2, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,077 ($269/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,355 ($765/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 30–31, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $719 ($719/night)
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Fantasy Island Resort II
Daytona Beach Shores, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($253/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 7, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,004 ($251/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 12, 2027 (13 nights)
- 3 bed/2 bath, sleeps 10
- $3,657 ($281/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,290 ($756/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,831 ($547/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,789 ($827/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,321 ($474/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 9, 2027 (10 nights)
- 3 bed/2 bath, sleeps 10
- $2,924 ($292/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 9, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,607 ($161/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Gulf Tides of Longboat Key
Longboat Key, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 9, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,399 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 30 – Feb 6, 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- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
Hyatt Windward Pointe Resort
Key West, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 12, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,000 ($154/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 30–31, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $423 ($423/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,451 ($922/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 7, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,343 ($168/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)