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
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,579 ($797/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,403 ($486/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
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Marriott's Desert Springs Villas
Palm Desert, California- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
Marriott Vacation Club at Los Sueños
Playa Jaco, Costa Rica- Feb 6–12, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($640/night)
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The Gardens at West Maui
Kapalua, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,440 ($206/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,917 ($417/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Feb 6–13, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,510 ($930/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,185 ($455/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,290 ($470/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Feb 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $4,712 ($942/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,217 ($602/night)
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Marriott's Summit Watch
Park City, Utah- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,000 ($1,000/night)
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Marriott's Summit Watch
Park City, Utah- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 6–13, 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- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's Shadow Ridge - The Villages
Palm Desert, California- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,368 ($338/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,181 ($454/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,072 ($1,296/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Feb 6–13, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $13,105 ($1,872/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 6–13, 2027 (7 nights)
- 1 bed/3 bath, sleeps 8
- $2,968 ($424/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,647 ($1,092/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,309 ($1,187/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,072 ($1,296/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,308 ($1,187/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 7–14, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,275 ($611/night)
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Marriott's Summit Watch
Park City, Utah- Feb 7–12, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,260 ($452/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,527 ($1,218/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,155 ($1,308/night)