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 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,731 ($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
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 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 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/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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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,497 ($500/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
- $3,290 ($470/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,072 ($1,296/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
- $7,110 ($1,016/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
- $2,532 ($362/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)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
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Sheraton Lakeside Terrace Villas at Mountain Vista
Avon, Colorado- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/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
- $8,200 ($1,171/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
- $5,748 ($821/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
- $7,655 ($1,094/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)
Aspen Mountain Residences
Aspen, Colorado- Feb 20–23, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($1,153/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 20–27, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,840 ($549/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
- $8,582 ($1,226/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Feb 20–25, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($714/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
- $5,534 ($791/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/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)
- Studio/1 bath, sleeps 4
- $3,513 ($502/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
- $7,328 ($1,047/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 21–28, 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 21–28, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,076 ($439/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,412 ($630/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 21–28, 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 21–26, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($485/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,256 ($751/night)
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Marriott's Desert Springs Villas
Palm Desert, California- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($986/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 21–26, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $1,440 ($288/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 21–26, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,178 ($436/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,654 ($1,093/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,914 ($583/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Feb 21–26, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,660 ($732/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 21–26, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,069 ($414/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,053 ($579/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 21–26, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,314 ($463/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Feb 21–26, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,562 ($712/night)
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Sheraton Desert Oasis
Scottsdale, Arizona- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)