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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $12,560 ($1,570/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,685 ($669/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/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
- $13,650 ($1,950/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
- $9,830 ($1,404/night)
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Garza Blanca Resort & Spa Cancun
Cancun, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $10,598 ($1,514/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $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
- $6,946 ($992/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,114 ($279/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $16,920 ($2,417/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,546 ($1,078/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,800 ($971/night)
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Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,198 ($171/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
- $7,639 ($1,091/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 19, 2026 – Jan 1, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $1,721 ($132/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $941 ($134/night)
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La Cabana Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,204 ($315/night)
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Grand Luxxe Spa Suites at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,176 ($1,311/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/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 Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,238 ($891/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 19, 2026 – Jan 1, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,964 ($228/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $16,920 ($2,417/night)
Marriott's Grande Vista
Orlando, Florida- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 3 bed/3 bath, sleeps 12
- $8,745 ($625/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
- $6,402 ($914/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,094 ($728/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,925 ($1,561/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19–22, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $648 ($216/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,565 ($938/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,500 ($214/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,407 ($1,201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19, 2026 – Jan 1, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $3,544 ($273/night)
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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
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,666 ($524/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19, 2026 – Jan 1, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,632 ($202/night)
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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
- $6,113 ($873/night)
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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
- $6,402 ($914/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $5,702 ($815/night)
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Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)