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
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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Club Wyndham Austin
Austin, Texas- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
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Club Wyndham Austin
Austin, Texas- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,795 ($256/night)
La Cabana Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,542 ($506/night)
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Club Wyndham Austin
Austin, Texas- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/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
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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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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Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
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Ocean Enclave by Hilton Grand Vacations
Myrtle Beach, South Carolina- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $15,830 ($2,261/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 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)
- 1 bed/2 bath, sleeps 4
- $5,202 ($743/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,233 ($1,748/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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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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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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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/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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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 18–24, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($548/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)
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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 Orange Tree Golf Resort
Scottsdale, Arizona- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($187/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 Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,036 ($1,148/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/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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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,057 ($580/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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/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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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
- $6,946 ($992/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–23, 2026 (5 nights)
- 3 bed/2 bath, sleeps 10
- $2,083 ($417/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)
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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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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $999 ($143/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–22, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,268 ($317/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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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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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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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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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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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
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/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)