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 Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,470 ($781/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,763 ($197/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,532 ($362/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
- $7,541 ($1,077/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,072 ($439/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $613 ($102/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($209/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,711 ($673/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,057 ($580/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–27, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,754 ($306/night)
Costa Linda Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,584 ($798/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,321 ($237/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($521/night)
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Club Wyndham Resort at Avon
Avon, Colorado- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,704 ($741/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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The Summit at Massanutten
McGaheysville, Virginia- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $1,219 ($174/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)
- 3 bed/2 bath, sleeps 8
- $13,050 ($1,864/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
- $7,110 ($1,016/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
- $10,380 ($1,483/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $12,004 ($1,715/night)
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Marriott Vacation Club Pulse at Custom House, Boston
Boston, Massachusetts- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/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
- $8,723 ($1,246/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18–24, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/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
- $2,366 ($296/night)
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The Manhattan Club
New York City, New York- Dec 18–21, 2026 (3 nights)
- 1 bed/2 bath, sleeps 4
- $2,085 ($695/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,427 ($102/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/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
- $4,930 ($704/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)
Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 18–26, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($412/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 18–25, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 18–27, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,185 ($132/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
- $7,274 ($1,039/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $9,835 ($1,405/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
- $3,540 ($506/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($224/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
- $3,894 ($556/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $14,194 ($1,014/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
- $7,274 ($1,039/night)