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 Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/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
- $6,020 ($860/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25, 2026 – Jan 6, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,462 ($122/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)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/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)
- 3 bed/3 bath, sleeps 10
- $6,510 ($930/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
- $4,930 ($704/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 25–31, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,079 ($180/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
- $5,366 ($767/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
- $4,494 ($642/night)
Verified & Protected
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
- $5,366 ($767/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)
- Studio/1 bath, sleeps 4
- $2,042 ($292/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
- $4,467 ($638/night)
Verified & Protected
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)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/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)
- Studio/1 bath, sleeps 4
- $2,096 ($299/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)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,238 ($891/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25, 2026 – Jan 6, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,776 ($231/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($299/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25, 2026 – Jan 6, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,122 ($177/night)
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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
- $9,726 ($1,389/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 6
- $4,603 ($658/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)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,506 ($301/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
- $5,693 ($813/night)
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CHOOSE YOUR OWN DATES
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
- $5,693 ($813/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25–31, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($216/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 2, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,310 ($289/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 2, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,695 ($212/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25–31, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,743 ($290/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,384 ($626/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,764 ($538/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,347 ($907/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($253/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,802 ($543/night)
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Coconut Mallory Marina & Resort
Key West, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/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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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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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
- $7,731 ($1,104/night)
Verified & Protected
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
- $8,502 ($1,215/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
- $3,188 ($455/night)