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- 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 15–20, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($572/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 18–25, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,459 ($637/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 19–24, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,929 ($586/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 19–25, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,802 ($467/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,876 ($696/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 19–21, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,495 ($748/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 19–26, 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- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,655 ($1,094/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 20–23, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,997 ($666/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,661 ($443/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,264 ($453/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 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- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,018 ($1,288/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,201 ($534/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,654 ($1,093/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,565 ($938/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,587 ($655/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,459 ($637/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,109 ($1,016/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,843 ($549/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($253/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,013 ($503/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($502/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($502/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,198 ($399/night)
Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 21–28, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,986 ($284/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,497 ($624/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 25 – Mar 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 26–28, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,222 ($611/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)