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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,617 ($517/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,290 ($1,327/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 19–25, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,871 ($645/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Feb 19–23, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $941 ($235/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,800 ($1,257/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,930 ($990/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Gold Point Resort
Breckenridge, Colorado- Feb 19–26, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $4,222 ($603/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Feb 19–26, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,978 ($283/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 1, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,602 ($289/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($220/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 1, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $3,583 ($398/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,217 ($602/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,366 ($296/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 3 bed/2 bath, sleeps 10
- $3,269 ($409/night)
La Cabana Beach Resort
Oranjestad, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,535 ($505/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,711 ($387/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Hacienda del Mar Resort
Cabo San Lucas, Mexico- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $5,312 ($759/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 4 bed/5 bath, sleeps 10
- $7,655 ($1,094/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,201 ($534/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,661 ($443/night)
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Marriott's Summit Watch
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,835 ($548/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,843 ($549/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,504 ($584/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,374 ($625/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,905 ($1,701/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,148 ($735/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Feb 20–27, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,336 ($619/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,733 ($533/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,213 ($459/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,069 ($581/night)