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 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,197 ($1,028/night)
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Gold Point Resort
Breckenridge, Colorado- Jan 1–8, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,874 ($839/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,838 ($977/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,564 ($938/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,266 ($1,038/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,908 ($701/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,930 ($990/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,763 ($1,109/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,404/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,380 ($1,483/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,083 ($1,012/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,893 ($699/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,696 ($242/night)
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Marriott's Royal Palms
Orlando, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,306 ($329/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,600 ($1,514/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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WorldMark Midway
Midway, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,976 ($854/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,976 ($854/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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The Villas at Disney's Grand Californian Hotel & Spa
Anaheim, California- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $3,213 ($1,071/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,679 ($668/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($822/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 1–5, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $479 ($120/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,584 ($1,226/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($2,465/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,852 ($1,693/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–7, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $684 ($342/night)