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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,582 ($1,226/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($216/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–24, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,743 ($290/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–24, 2026 (6 nights)
- 3 bed/2 bath, sleeps 10
- $2,397 ($399/night)
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Casa Dorada at Medano Beach
Cabo San Lucas, Mexico- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,743 ($290/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,834 ($1,405/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,740 ($1,249/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,579 ($940/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,099 ($728/night)
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Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,403 ($486/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,099 ($157/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
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Costa Linda Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($385/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($1,095/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–26, 2026 (8 nights)
- 1 bed/2 bath, sleeps 4
- $7,873 ($984/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $14,740 ($2,106/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $8,740 ($1,249/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,382 ($1,055/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,422/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,853 ($1,265/night)
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Falcon Point
Avon, Colorado- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,911 ($844/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,289 ($898/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,993 ($1,713/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,211 ($602/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($220/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,181 ($1,312/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–26, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,366 ($296/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,350 ($1,050/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–31, 2026 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,551 ($196/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,838 ($977/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,294 ($471/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,272 ($1,039/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–31, 2026 (13 nights)
- 2 bed/2 bath, sleeps 8
- $3,696 ($284/night)
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Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)