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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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Feb 13–20, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,669 ($1,524/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 13–27, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $5,397 ($385/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,851 ($264/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,110 ($1,016/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($1,545/night)
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Grand Colorado on Peak 8
Breckenridge, Colorado- Feb 13–20, 2027 (7 nights)
- 1 bed/1.5 bath, sleeps 4
- $5,911 ($844/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,610 ($944/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
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Sheraton Vistana Villages
Orlando, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–19, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,848 ($407/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,591 ($656/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,688 ($384/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Mayan Palace Acapulco
Acapulco, Mexico- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 7
- $4,290 ($613/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 13–20, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,181 ($1,312/night)
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Mayan Palace Acapulco
Acapulco, Mexico- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 7
- $4,290 ($613/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,470 ($781/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 13–20, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,745 ($1,249/night)
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Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Feb 13–20, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,977 ($1,140/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Feb 13–20, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,977 ($1,140/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 13–18, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 13–18, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,352 ($270/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,092 ($156/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 13–18, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,839 ($368/night)
Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 13–27, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,920 ($209/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,237 ($462/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Feb 13–18, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($152/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,512 ($216/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Feb 13–17, 2027 (4 nights)
- 3 bed/2 bath, sleeps 8
- $940 ($235/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,237 ($462/night)