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
- $4,276 ($611/night)
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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
- $6,782 ($969/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,302 ($615/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
- $2,750 ($550/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–21, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($216/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,840 ($263/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–21, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,743 ($290/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–21, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $2,397 ($399/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,341 ($557/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 15–21, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,743 ($290/night)
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Daytona Beach Regency
Daytona Beach, Florida- Feb 17–22, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,220 ($244/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Feb 17–21, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $3,687 ($922/night)
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Daytona Beach Regency
Daytona Beach, Florida- Feb 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $1,109 ($222/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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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)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 19 – Mar 1, 2027 (10 nights)
- 3 bed/2 bath, sleeps 10
- $4,141 ($414/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 19 – Mar 1, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($222/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 19 – Mar 1, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,990 ($299/night)
Eagle's Nest Beach Resort
Marco Island, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/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
- $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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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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Marriott's Oceana Palms
Riviera Beach, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Feb 19–23, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,065 ($516/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 19–25, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,969 ($661/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 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
- $5,802 ($829/night)
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The Galleon Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/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
- $6,783 ($969/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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,126 ($447/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)
- 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
- $6,891 ($984/night)
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Vacation Village at Weston
Weston, Florida- Feb 20–27, 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- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,586 ($370/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,746 ($392/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
- $6,891 ($984/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 2, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,837 ($284/night)