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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25–30, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($224/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,090 ($1,156/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,380 ($626/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,629 ($204/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,854 ($1,265/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,405 ($201/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,162 ($1,452/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,922 ($275/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26–30, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $555 ($139/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,230 ($319/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,056 ($1,008/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $901 ($129/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 4, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($196/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,268 ($181/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,458 ($208/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,891 ($270/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,277 ($213/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,403 ($486/night)
Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,894 ($556/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($486/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($303/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–31, 2026 (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- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,183 ($312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,309 ($1,187/night)
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Marriott's Imperial Palm Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $4,112 ($588/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,260 ($323/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,786 ($541/night)
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Club Wyndham Palm-Aire
Pompano Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26–30, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($222/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Marriott's Sabal Palms
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($284/night)