Winter Timeshare Rentals

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$6,892 ($985/night)

Verified & Protected

Sheraton Steamboat Resort Villas

Steamboat Springs, Colorado

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

Marriott's Aruba Ocean Club

Palm Beach, Aruba

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$8,853 ($1,265/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected

Sheraton Steamboat Resort Villas

Steamboat Springs, Colorado

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

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$10,380 ($1,483/night)

Verified & Protected

The Westin Lagunamar Ocean Resort Villas & Spa

Cancun, Mexico

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

Verified & Protected

The Westin St. John - Virgin Grand Villas

Cruz Bay, St. John (USVI)

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 6
$8,745 ($1,249/night)

Verified & Protected

The Westin St. John - Coral Vista Villas

Cruz Bay, St. John (USVI)

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Grand Desert

Las Vegas, Nevada

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,791 ($256/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
$4,385 ($626/night)

Verified & Protected

Villa del Arco Beach Resort & Spa

Cabo San Lucas, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/4 bath, sleeps 8
$11,470 ($1,639/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,222 ($603/night)

Verified & Protected

Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,404 ($486/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Grand Desert

Las Vegas, Nevada

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,154 ($165/night)

Verified & Protected

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
$15,558 ($2,222/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,963 ($995/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,472 ($1,210/night)

Verified & Protected

The Ritz-Carlton Club, St. Thomas

East End, St. Thomas (USVI)

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2.5 bath, sleeps 6
$19,645 ($3,274/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$12,777 ($1,825/night)

Verified & Protected

WorldMark Canmore - Banff

Canmore, Alberta, Canada

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($315/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,056 ($1,008/night)

Verified & Protected

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)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$4,214 ($602/night)

Verified & Protected

Kalia Suites by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$4,440 ($634/night)

Verified & Protected

Villa del Palmar Cancun Luxury Beach Resort & Spa

Cancun, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 6
$4,603 ($658/night)

Verified & Protected

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)

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)

Verified & Protected

Sheraton Steamboat Resort Villas

Steamboat Springs, Colorado

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 6
$6,238 ($1,040/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
$9,830 ($1,404/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
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's OceanWatch Villas at Grande Dunes

Myrtle Beach, South Carolina

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,711 ($673/night)

Verified & Protected

The Ritz-Carlton Club, St. Thomas

East End, St. Thomas (USVI)

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2.5 bath, sleeps 6
$17,355 ($2,479/night)

Verified & Protected

Sheraton Steamboat Resort Villas

Steamboat Springs, Colorado

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$7,755 ($1,108/night)

Verified & Protected

Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/night)

Verified & Protected

Villa del Palmar Cabo San Lucas

Cabo San Lucas, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 6
$2,205 ($315/night)

Verified & Protected

Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

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 MountainSide at Park City

Park City, Utah

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,259 ($1,323/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
$10,216 ($1,460/night)

Verified & Protected

Valdoro Mountain Lodge, a Hilton Grand Vacations Club

Breckenridge, Colorado

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,830 ($1,404/night)

Verified & Protected

Westgate Smoky Mountain Resort & Water Park

Gatlinburg, Tennessee

Dec 26, 2026 – Jan 2, 2027 (7 nights)
4 bed/4 bath, sleeps 16
$3,704 ($529/night)

Verified & Protected

The Ritz-Carlton Club, St. Thomas

East End, St. Thomas (USVI)

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3.5 bath, sleeps 8
$20,625 ($2,946/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
$8,413 ($1,202/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

Verified & Protected

The Westin Lagunamar Ocean Resort Villas & Spa

Cancun, Mexico

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,312 ($759/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)