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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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,850 ($475/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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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 20–23, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,997 ($666/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,459 ($637/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Marriott's Desert Springs Villas
Palm Desert, California- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/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
- $5,094 ($728/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)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,840 ($549/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $12,010 ($1,716/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/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
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,898 ($1,557/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,527 ($361/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,350 ($478/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
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The Galleon Resort
Key West, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,636 ($377/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
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,466 ($495/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,001 ($429/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/night)
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Marriott's Shadow Ridge - The Villages
Palm Desert, California- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,352 ($270/night)
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Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,851 ($264/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
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Feb 20–27, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,652 ($1,522/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,108 ($1,444/night)
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Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Feb 20–27, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,908 ($701/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,337 ($334/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,126 ($447/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,164 ($1,024/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Royal Haciendas
Playa del Carmen, Mexico- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
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Club Wyndham Oceanside Pier Resort
Oceanside, California- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Feb 20–27, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,706 ($1,529/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)