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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Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $4,565 ($652/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,107 ($872/night)
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The Westin Mission Hills Villas
Rancho Mirage, California- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,358 ($194/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Coral Sands Resort
George Town, Grand Cayman, Cayman Islands- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($253/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,600 ($514/night)
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Four Seasons Residence Club Aviara
Carlsbad, California- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 5–11, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $946 ($158/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–10, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $670 ($134/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–9, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–19, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $7,327 ($523/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 5–11, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,431 ($239/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($221/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,250 ($464/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $4,498 ($643/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–13, 2026 (8 nights)
- 3 bed/2 bath, sleeps 10
- $1,856 ($232/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–11, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($831/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
Royal Haciendas
Playa del Carmen, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($346/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Grand Beach Resort
Orlando, Florida- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,893 ($270/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,347 ($907/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)