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.
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($424/night)
The Royal Sands
Cancun, Mexico- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
The Royal Sands
Cancun, Mexico- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,478 ($354/night)
WorldMark Kihei Resort
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,856 ($265/night)
Hyatt High Sierra Lodge
Incline Village, Nevada- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,382 ($483/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,136 ($162/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $12,042 ($1,720/night)
The Westin Riverfront Mountain Villas
Avon, Colorado- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,535 ($219/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,129 ($876/night)
Hyatt Vacation Club at Sirena del Mar
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,579 ($1,083/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,687 ($527/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,924 ($1,561/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,410 ($1,201/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,894 ($271/night)
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
The Resort at Diamante
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 1 bed/1.5 bath, sleeps 4
- $2,123 ($303/night)
Garza Blanca Resort & Spa Los Cabos
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,657 ($380/night)
Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,123 ($303/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,832 ($690/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,000 ($714/night)
Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,169 ($292/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,679 ($668/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($819/night)
The Royal Sands
Cancun, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,470 ($1,639/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,915 ($2,416/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,638 ($806/night)
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,734 ($391/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
The Galleon Resort
Key West, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($543/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,173 ($1,310/night)