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 Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,162 ($595/night)
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Club Wyndham Clearwater Beach Resort
Clearwater, Florida- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,204 ($441/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
- $5,361 ($766/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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Four Seasons Residence Club Aviara
Carlsbad, California- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($547/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
- $11,252 ($1,607/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
- $5,748 ($821/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
- $7,464 ($1,066/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
- $8,418 ($1,203/night)
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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
- $9,290 ($1,327/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
- $5,693 ($813/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,207 ($315/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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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 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 Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($1,545/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
- $5,175 ($739/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 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 Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,506 ($301/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)
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 10
- $18,550 ($2,650/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 Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,325 ($865/night)
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Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,801 ($829/night)
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Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Marriott Vacation Club at Los Sueños
Playa Jaco, Costa Rica- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/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
- $4,493 ($642/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
- $8,036 ($1,148/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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/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)
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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,932 ($281/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
- $11,252 ($1,607/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $7,328 ($523/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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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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The Summit at Massanutten
McGaheysville, Virginia- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $1,439 ($206/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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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 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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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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,506 ($301/night)