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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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,476 ($211/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,712 ($673/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $13,650 ($1,950/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,277 ($319/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,586 ($370/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,184 ($883/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,620 ($946/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($549/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,138 ($523/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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Garza Blanca Resort & Spa Los Cabos
Cabo San Lucas, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,129 ($876/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,257 ($751/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $24,005 ($3,429/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,652 ($1,522/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $5,420 ($903/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,375 ($2,339/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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Westgate Park City Resort & Spa
Park City, Utah- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,039 ($434/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,972 ($1,996/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
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Villa La Valencia Beach Resort & Spa
San Jose del Cabo, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $3,949 ($564/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($813/night)
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Club Regina Los Cabos
San Jose del Cabo, Mexico- Dec 20–27, 2026 (7 nights)
- 1 bed/1.5 bath, sleeps 4
- $2,276 ($325/night)
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($284/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,600 ($1,086/night)
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Marriott's Harbour Lake
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($813/night)
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Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,833 ($262/night)
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Villa La Estancia Beach Resort & Spa Riviera Nayarit
Nuevo Vallarta, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $5,475 ($782/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
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Marriott's Shadow Ridge - The Villages
Palm Desert, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,053 ($579/night)
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Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 10
- $1,769 ($253/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,887 ($984/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,432 ($1,633/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)