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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 31 – Feb 5, 2027 (5 nights)
- 1 bed/1 bath, sleeps 6
- $1,818 ($364/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 31 – Feb 5, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($1,095/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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 31 – Feb 6, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,222 ($370/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 31 – Feb 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $17,465 ($2,495/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
- $7,218 ($1,031/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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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 31 – Feb 4, 2027 (4 nights)
- 3 bed/2 bath, sleeps 8
- $3,949 ($987/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 31 – Feb 7, 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- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,181 ($1,312/night)
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 31 – Feb 5, 2027 (5 nights)
- 3 bed/3 bath, sleeps 8
- $5,475 ($1,095/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,546 ($1,078/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,658 ($237/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,692 ($813/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 1–8, 2027 (7 nights)
- Studio/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 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,568 ($510/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Feb 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,431 ($686/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,020 ($860/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,764 ($1,109/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 1–5, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($470/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Feb 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,707 ($672/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 2–14, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $7,677 ($640/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,128 ($875/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Feb 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,218 ($1,031/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 4–11, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,076 ($439/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 4–11, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,202 ($743/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 4–11, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Feb 5–12, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Feb 5–10, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($397/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,766 ($681/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 5–8, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,752 ($584/night)
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Club Wyndham Avenue Plaza
New Orleans, Louisiana- Feb 5–10, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $1,931 ($386/night)