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- 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
- $5,748 ($821/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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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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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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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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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 Old Key West Resort
Lake Buena Vista, Florida- Feb 21–24, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,198 ($399/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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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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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,497 ($624/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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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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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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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 25 – Mar 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/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)
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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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,071 ($1,296/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,478 ($497/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Feb 27 – Mar 2, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,515 ($505/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,732 ($819/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,910 ($844/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,869 ($696/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)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,616 ($1,374/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($253/night)
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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)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,311 ($1,187/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,199 ($1,171/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,238 ($891/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 27 – Mar 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,238 ($891/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 28 – Mar 5, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $6,565 ($1,313/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,459 ($637/night)
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Hyatt Beach House Resort
Key West, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 28 – Mar 6, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,709 ($618/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,843 ($549/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 28 – Mar 6, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,484 ($414/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 28 – Mar 6, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,201 ($534/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 25, 2027 – Jan 1, 2028 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,660 ($237/night)