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.
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,581 ($369/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,123 ($303/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,276 ($325/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,302 ($260/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,302 ($260/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,743 ($549/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,302 ($260/night)
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
Grand Solmar Pacific Dunes Resort Golf & Spa
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,274 ($1,039/night)
Simpson Bay Resort and Marina
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,849 ($264/night)
WorldMark Steamboat Springs Resort
Steamboat Springs, Colorado- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Southern California Beach Club
Oceanside, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,505 ($358/night)
The Westin Kierland Villas
Scottsdale, Arizona- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,153 ($450/night)
Club Wyndham Resort at Avon
Avon, Colorado- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,470 ($1,639/night)
Tahiti Village
Las Vegas, Nevada- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,657 ($380/night)
Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,649 ($521/night)
Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,185 ($455/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,274 ($1,039/night)
Club Wyndham Midtown 45
New York City, New York- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 2
- $2,314 ($386/night)
Club Wyndham Resort at Avon
Avon, Colorado- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($160/night)
Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $892 ($149/night)
Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($134/night)
The Westin Mission Hills Villas
Rancho Mirage, California- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($497/night)
Grand Solmar Pacific Dunes Resort Golf & Spa
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,200 ($1,171/night)
Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,291 ($470/night)
Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
Wyndham Vacation Resorts Royal Garden at Waikiki
Honolulu, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Dec 27–31, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $535 ($134/night)
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Dec 27–30, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $463 ($154/night)
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Dec 27–30, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $415 ($138/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,113 ($1,159/night)
Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,085 ($298/night)
The Westin Mission Hills Villas
Rancho Mirage, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,819 ($2,260/night)
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/4 bath, sleeps 10
- $14,636 ($2,091/night)
The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,432 ($1,633/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,740 ($820/night)
Marriott's Shadow Ridge - The Villages
Palm Desert, California- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,840 ($406/night)
Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,749 ($393/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,369 ($2,053/night)
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,428 ($347/night)
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $9,290 ($1,327/night)