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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Villas at Disneyland Hotel
Anaheim, California- Jan 16–22, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,321 ($387/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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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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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,830 ($1,404/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
- $4,930 ($704/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,291 ($470/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,840 ($549/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,291 ($470/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–20, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,220 ($305/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 16–22, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,145 ($691/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,406 ($481/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,824 ($689/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,824 ($689/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,510 ($1,073/night)
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Sheraton Desert Oasis
Scottsdale, Arizona- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,313 ($330/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,637 ($546/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,583 ($798/night)
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Villas at Disneyland Hotel
Anaheim, California- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,125 ($375/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,775 ($1,111/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($702/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,113 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,982 ($1,140/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–21, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($715/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 17–22, 2027 (5 nights)
- 3 bed/3.5 bath, sleeps 8
- $9,835 ($1,967/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jan 17–22, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($277/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)