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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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($891/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,786 ($541/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,328 ($761/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
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Club Wyndham Royal Vista
Pompano Beach, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,772 ($396/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 16–26, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($820/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,898 ($1,557/night)
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The Cliff Club at Snowbird
Snowbird, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $13,105 ($1,872/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,290 ($1,327/night)
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Grand Timber Lodge
Breckenridge, Colorado- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,412 ($345/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 9
- $5,910 ($844/night)
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Royal Haciendas
Playa del Carmen, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,745 ($392/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,290 ($756/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 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- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Royal Cancun (Formerly Club Internacional de Cancun)
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/1 bath, sleeps 5
- $2,423 ($346/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 16–23, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,707 ($1,530/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,693 ($813/night)
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The Ritz-Carlton Club, Aspen Highlands
Aspen, Colorado- Jan 16–23, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,562 ($1,366/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($408/night)
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Novaispania Residences by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 4 bed/4.5 bath, sleeps 12
- $9,071 ($1,296/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,941 ($420/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 16–22, 2027 (6 nights)
- 1 bed/1 bath, sleeps 6
- $2,314 ($386/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,759 ($552/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–17, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $586 ($586/night)
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 3 bed/4 bath, sleeps 10
- $11,470 ($1,639/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,616 ($1,374/night)