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 Orange Tree Golf Resort
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,742 ($348/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Westgate Park City Resort & Spa
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $935 ($312/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
- $7,464 ($1,066/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Wyndham Reef Resort
East End, Grand Cayman, Cayman Islands- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,020 ($860/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,838 ($977/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 9
- $5,910 ($844/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,345 ($469/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
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,007 ($858/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,039 ($720/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–17, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $586 ($586/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,673 ($558/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,946 ($707/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
- $5,693 ($813/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,487 ($1,070/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,802 ($829/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,076 ($439/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–29, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,000 ($154/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,920 ($209/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
- $4,058 ($580/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)