Winter Timeshare Rentals

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Wyndham Reef Resort

East End, Grand Cayman, Cayman Islands

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 2
$3,840 ($549/night)

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Kalia Suites by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,017 ($431/night)

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The Westin Lagunamar Ocean Resort Villas & Spa

Cancun, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,786 ($541/night)

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Villa del Arco Beach Resort & Spa

Cabo San Lucas, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$3,077 ($440/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,977 ($711/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,803 ($1,543/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,380 ($626/night)

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Kalia Suites by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,786 ($541/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$7,495 ($1,071/night)

Verified & Protected Voted Top Pick 2026

Pueblo Bonito Sunset Beach Resort & Spa

Cabo San Lucas, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 10
$7,651 ($1,093/night)

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Club Wyndham Park City

Park City, Utah

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,129 ($876/night)

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Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$5,748 ($821/night)

Verified & Protected Voted Top Pick 2026

Harborside Resort at Atlantis

Paradise Island, Bahamas

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

Verified & Protected Voted Top Pick 2026

The Westin Kierland Villas

Scottsdale, Arizona

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,565 ($652/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

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Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$12,886 ($1,841/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,891 ($270/night)

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The Westin Lagunamar Ocean Resort Villas & Spa

Cancun, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected Voted Top Pick 2026

Harborside Resort at Atlantis

Paradise Island, Bahamas

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$4,183 ($598/night)

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Divi Village Golf and Beach Resort

Oranjestad, Aruba

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,314 ($331/night)

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Villa del Palmar Flamingos

Nuevo Vallarta, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 6
$3,839 ($548/night)

Verified & Protected Voted Top Pick 2026

Marriott's MountainSide at Park City

Park City, Utah

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,199 ($1,171/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$7,873 ($1,125/night)

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The Westin Lagunamar Ocean Resort Villas & Spa

Cancun, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,423 ($346/night)

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Hilton Vacation Club Lake Tahoe Resort

South Lake Tahoe, California

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,380 ($626/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,094 ($728/night)

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Grand Lodge on Peak 7

Breckenridge, Colorado

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$12,995 ($1,856/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$6,510 ($930/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 2
$4,112 ($588/night)

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Divi Village Golf and Beach Resort

Oranjestad, Aruba

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,123 ($303/night)

Hanalei Bay Resort

Princeville, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,192 ($1,027/night)

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The Ridge Tahoe

Stateline, Nevada

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 2
$944 ($135/night)

Verified & Protected Voted Top Pick 2026

Marriott's MountainSide at Park City

Park City, Utah

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,726 ($1,389/night)

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Holiday Inn Club Vacations New Orleans Resort

New Orleans, Louisiana

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,186 ($455/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

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The Ritz-Carlton Club, Vail

Vail, Colorado

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 6
$15,285 ($2,548/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,181 ($1,312/night)

Verified & Protected Voted Top Pick 2026

Marriott's Newport Coast Villas

Newport Coast, California

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$15,067 ($2,152/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,749 ($393/night)

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The Club at Solaz, Los Cabos

San Jose del Cabo, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/4 bath, sleeps 12
$15,481 ($2,212/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,749 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,181 ($1,312/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,502 ($1,215/night)