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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 16–22, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,251 ($542/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,200 ($314/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,964 ($852/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,898 ($1,557/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,650 ($1,093/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–22, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,598 ($766/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,775 ($1,111/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,650 ($189/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($80/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,054 ($290/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,911 ($844/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,929 ($704/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $746 ($249/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $603 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,901 ($700/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,637 ($546/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,802 ($467/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,100 ($525/night)
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Villas at Disneyland Hotel
Anaheim, California- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,674 ($446/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)