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 MountainSide at Park City
Park City, Utah- Jan 24–28, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($633/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–28, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($715/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,467 ($493/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Villas at Disneyland Hotel
Anaheim, California- Jan 24–27, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,125 ($375/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 24–30, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $6,666 ($1,111/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/night)
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,214 ($243/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 25–29, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,118 ($529/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 25 – Feb 2, 2027 (8 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($344/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 25–29, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,594 ($398/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 25 – Feb 1, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $2,831 ($404/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 25 – Feb 1, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,507 ($1,358/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 26 – Feb 1, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($531/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 26 – Feb 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 26–31, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,743 ($549/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 26–29, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($1,316/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 28 – Feb 4, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,181 ($454/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 28 – Feb 4, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 29 – Feb 4, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($386/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 29 – Feb 5, 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- Jan 29 – Feb 5, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,560 ($1,794/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 29–31, 2027 (2 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($1,756/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,673 ($953/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,730 ($533/night)
Marriott's Summit Watch
Park City, Utah- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,884 ($983/night)
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The Point at Poipu
Koloa, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,275 ($611/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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Casa Dorada at Medano Beach
Cabo San Lucas, Mexico- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/2 bath, sleeps 2
- $7,437 ($1,062/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 29 – Feb 2, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,131 ($533/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,948 ($564/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
- $6,564 ($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)
- 2 bed/2 bath, sleeps 8
- $7,490 ($1,070/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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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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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/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
- $7,328 ($1,047/night)