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 Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Sheraton Broadway Resort Villas
Myrtle Beach, South Carolina- Dec 19–30, 2026 (11 nights)
- 2 bed/2 bath, sleeps 8
- $665 ($60/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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Divi Little Bay Beach & Racquet Club
Little Bay Beach, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,380 ($1,483/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,462 ($1,495/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $19,100 ($2,729/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,742 ($249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,091 ($1,156/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,856 ($265/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($362/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19–25, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,590 ($265/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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Woodstone at Massanutten & Woodstone Casas
McGaheysville, Virginia- Dec 19–26, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $2,314 ($331/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,143 ($1,592/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $15,067 ($1,076/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,687 ($527/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,690 ($1,242/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,693 ($813/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $10,380 ($1,483/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,742 ($249/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,550 ($221/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19–25, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,590 ($265/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,925 ($1,561/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,726 ($1,389/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,910 ($844/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,825 ($546/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,129 ($876/night)
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Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,836 ($548/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,488 ($1,498/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($486/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,056 ($1,008/night)