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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,651 ($1,093/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
- $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
- $11,470 ($1,639/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 2
- $1,165 ($166/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($299/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
- $8,962 ($1,280/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
- $3,077 ($440/night)
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Coconut Mallory Marina & Resort
Key West, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 3, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,917 ($213/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,764 ($1,109/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 3, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($293/night)
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Club Wyndham Santa Barbara
Pompano Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,724 ($246/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 25–31, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,039 ($173/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
- $16,484 ($2,355/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 25–31, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,585 ($264/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- 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 Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/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
- $7,928 ($1,132/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $19,100 ($2,729/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/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
- $3,764 ($538/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $9,290 ($1,327/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
- $7,110 ($1,016/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $7,655 ($1,094/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
- $4,385 ($626/night)
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Four Seasons Residence Club Aviara
Carlsbad, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,925 ($1,561/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,990 ($1,284/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
- $1,165 ($166/night)
Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/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
- $9,835 ($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
- $14,848 ($2,121/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 2
- $3,268 ($467/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
- $3,840 ($549/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,560 ($1,794/night)
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Vista Mirage Resort
Palm Springs, California- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/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)
- 1 bed/1 bath, sleeps 4
- $6,320 ($903/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
- $15,830 ($2,261/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,565 ($938/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 2, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,695 ($212/night)