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 Aruba Ocean Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,185 ($455/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,866 ($267/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 9–16, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,279 ($326/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 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- Jan 10–17, 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- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,638 ($806/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,510 ($1,085/night)
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Marriott's Summit Watch
Park City, Utah- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 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- Jan 10–15, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,488 ($298/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,140 ($591/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–19, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($608/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 10–13, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,346 ($449/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $14,740 ($2,106/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,892 ($1,149/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,242 ($248/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,712 ($542/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,298 ($550/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $3,082 ($616/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,726 ($1,389/night)