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 Point at Poipu
Koloa, Hawaii- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($912/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
- $5,584 ($798/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
- $6,120 ($874/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- 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 Aruba Ocean 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 Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,957 ($708/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,692 ($385/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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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/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)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/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
- $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
- $5,148 ($735/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
- $6,892 ($985/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,821 ($689/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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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $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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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/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)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,350 ($1,050/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
- $4,276 ($611/night)
The Point at Poipu
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,599 ($657/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
- $2,711 ($542/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,887 ($472/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,347 ($587/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,821 ($689/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
- $2,903 ($415/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,345 ($469/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
- $4,494 ($642/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,821 ($689/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Marriott's Grande Vista
Orlando, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,192 ($548/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,192 ($548/night)
Royal Haciendas
Playa del Carmen, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)