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 Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $15,939 ($2,277/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,635 ($1,234/night)
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Windjammer Landing Villa Beach Resort
Castries, St. Lucia- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $3,949 ($564/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $11,470 ($1,639/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,884 ($983/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($1,218/night)
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Sheraton Lakeside Terrace Villas at Mountain Vista
Avon, Colorado- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,707 ($1,530/night)
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,472 ($1,210/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27–31, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $3,458 ($865/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $7,099 ($1,183/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $5,473 ($782/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
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Villa La Valencia Beach Resort & Spa
San Jose del Cabo, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,458 ($494/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
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Marriott's Phuket Beach Club
Phuket, Thailand- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,303 ($2,043/night)
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Four Seasons Residence Club Aviara
Carlsbad, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,474 ($782/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,744 ($1,249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,199 ($1,171/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2026 – Jan 8, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $5,768 ($481/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $6,227 ($1,038/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,308 ($1,187/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,800 ($1,543/night)
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Westgate Park City Resort & Spa
Park City, Utah- Dec 27, 2026 – Jan 3, 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- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,764 ($1,109/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,925 ($985/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,146 ($1,164/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,183 ($598/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($322/night)
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Voted Top Pick 2026
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,764 ($1,109/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Marriott's Harbour Lake
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,876 ($696/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)