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 Aruba Ocean Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,775 ($825/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,321 ($474/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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Caribbean Palm Village
Oranjestad, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,769 ($253/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,758 ($537/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,871 ($553/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,779 ($540/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,350 ($478/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $10,380 ($1,483/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 13, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,215 ($301/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 13, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,378 ($241/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 13, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,337 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 13, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,288 ($163/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,109 ($1,016/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,355 ($765/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,521 ($646/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 13, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,215 ($301/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 9, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,924 ($292/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,365 ($766/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,996 ($999/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,445 ($349/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 31 – Feb 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $6,892 ($985/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,077 ($440/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,545 ($1,078/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)