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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Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,375 ($2,339/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,038 ($720/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,655 ($1,094/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,564 ($938/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–30, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $870 ($174/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($236/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($1,218/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $106,942 ($15,277/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,721 ($1,960/night)
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Westgate Vacation Villas
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,314 ($331/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–31, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $979 ($163/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,705 ($1,529/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,984 ($855/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
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CHOOSE YOUR OWN DATES
Club Wyndham National Harbor
National Harbor, Maryland- Dec 25–31, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,135 ($356/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,557 ($508/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,835 ($1,405/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $21,388 ($3,055/night)
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Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 5 bed/5 bath, sleeps 20
- $21,825 ($3,118/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,611 ($516/night)
La Cabana Beach Resort
Oranjestad, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,944 ($1,421/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,579 ($1,083/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Marriott's Desert Springs Villas
Palm Desert, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 25–28, 2026 (3 nights)
- 1 bed/2 bath, sleeps 5
- $4,276 ($1,425/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($253/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,028 ($1,290/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,173 ($1,310/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,153 ($450/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 4 bed/4 bath, sleeps 12
- $7,655 ($1,094/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,930 ($704/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,925 ($1,561/night)
The Ritz Carlton Club, San Francisco
San Francisco, California- Dec 25–28, 2026 (3 nights)
- 1 bed/1.5 bath, sleeps 4
- $2,478 ($826/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,623 ($1,518/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
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Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
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Desert Breezes Resort
Palm Desert, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,135 ($2,019/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,971 ($567/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,467 ($638/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)