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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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Dec 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,096 ($419/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 11–16, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($419/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,058 ($1,151/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,382 ($483/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,243 ($892/night)
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Corazon Cabo Resort & Spa
Cabo San Lucas, Mexico- Dec 12–19, 2026 (7 nights)
- 3 bed/4 bath, sleeps 12
- $6,838 ($977/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,204 ($315/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Villa del Palmar Cabo San Lucas
Cabo San Lucas, Mexico- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,069 ($438/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,330 ($619/night)
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Marriott's Summit Watch
Park City, Utah- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,579 ($797/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,745 ($392/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,344 ($478/night)
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Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,876 ($696/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Marriott's Summit Watch
Park City, Utah- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,440 ($206/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,925 ($1,561/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Corazon Cabo Resort & Spa
Cabo San Lucas, Mexico- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
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Royal Islander Club la Plage
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,486 ($498/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($922/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,778 ($1,397/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 9
- $5,257 ($1,314/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,488 ($355/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,820 ($689/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,914 ($416/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,031 ($576/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–16, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,132 ($447/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)