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 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,214 ($243/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Marriott's Desert Springs Villas
Palm Desert, California- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($1,545/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,336 ($334/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,586 ($1,084/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Marriott's Summit Watch
Park City, Utah- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,442 ($777/night)
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Marriott's Summit Watch
Park City, Utah- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,984 ($712/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,412 ($630/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 14–19, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,178 ($436/night)
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Westgate Park City Resort & Spa
Park City, Utah- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,015 ($1,716/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,472 ($1,210/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,996 ($1,857/night)
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Westgate Park City Resort & Spa
Park City, Utah- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Marriott's Summit Watch
Park City, Utah- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,557 ($1,365/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($1,545/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 14–19, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,689 ($538/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,856 ($837/night)
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Marriott's Grande Vista
Orlando, Florida- Feb 14–21, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,240 ($463/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 6
- $1,330 ($266/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,943 ($1,420/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($604/night)
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Marriott's Summit Watch
Park City, Utah- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,925 ($1,561/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 15–20, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($572/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)