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 Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,638 ($806/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/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
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,071 ($1,296/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,693 ($385/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 2–4, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,334 ($667/night)
Costa Linda Beach Resort
Oranjestad, Aruba- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($822/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,190 ($456/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 2–4, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $1,109 ($554/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 2–8, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,199 ($533/night)
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,469 ($496/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,766 ($753/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
- $3,268 ($467/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
- $2,641 ($377/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
- $10,380 ($1,483/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/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,851 ($836/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,821 ($403/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $1,769 ($253/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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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,403 ($486/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/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
- $5,910 ($844/night)
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Marriott's Summit Watch
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,420 ($774/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,491 ($784/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
- $7,110 ($1,016/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/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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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($187/night)
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Royal Haciendas
Playa del Carmen, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/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
- $4,930 ($704/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
- $6,074 ($868/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
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)