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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Villas at Disneyland Hotel
Anaheim, California- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,674 ($446/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,604 ($434/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,554 ($511/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,554 ($511/night)
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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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/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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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 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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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)
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
- $7,219 ($1,031/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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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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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 26–30, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,985 ($496/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 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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 28 – Feb 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/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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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)
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 28 – Feb 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 6
- $1,796 ($359/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
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 #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)
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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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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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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 Ritz-Carlton Club, Vail
Vail, Colorado- Jan 29–31, 2027 (2 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($1,756/night)
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
- $4,603 ($658/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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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
- $3,622 ($517/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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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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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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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
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/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)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Jan 30 – Feb 6, 2027 (7 nights)
- 6 bed/6 bath, sleeps 12
- $5,475 ($782/night)
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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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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,105 ($1,015/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,294 ($471/night)