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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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,647 ($329/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,978 ($283/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,726 ($1,389/night)
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Morritt's The Londoner
East End, Grand Cayman, Cayman Islands- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($152/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,271 ($610/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $15,285 ($2,184/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,382 ($1,055/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($665/night)
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Royal Islander Club la Plage
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,440 ($206/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,559 ($520/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $875 ($292/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($120/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,467 ($176/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,924 ($561/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,996 ($1,857/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,528 ($306/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,802 ($543/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,138 ($224/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 2–8, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,298 ($550/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 2–9, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,105 ($301/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,999 ($600/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,437 ($1,062/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–16, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $8,647 ($618/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,219 ($460/night)
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Kona Coast Resort
Kailua-Kona, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,772 ($396/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,999 ($600/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,115 ($445/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)