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.
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,920 ($1,560/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($731/night)
Verified & Protected
Sunburst Resort
Steamboat Springs, Colorado- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,544 ($221/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,711 ($194/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,650 ($189/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($80/night)
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Verified & Protected
Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
Verified & Protected
Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,559 ($520/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $875 ($292/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,172 ($391/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,782 ($969/night)
Club Wyndham Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,469 ($496/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,742 ($249/night)
Verified & Protected
Hyatt Vacation Club at Northstar Lodge
Truckee, California- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,797 ($828/night)
Verified & Protected
Grand Solmar Pacific Dunes Resort Golf & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,358 ($765/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,528 ($306/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–8, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($258/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–8, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,640 ($440/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($152/night)
Verified & Protected
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,402 ($486/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $7,382 ($1,055/night)
Verified & Protected
Hyatt Main Street Station, A Hyatt Residence Club
Breckenridge, Colorado- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,712 ($673/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,821 ($403/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Verified & Protected
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,462 ($495/night)
Verified & Protected
Royal Haciendas
Playa del Carmen, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,584 ($798/night)
Verified & Protected
Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 2–7, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,284 ($657/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,957 ($422/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,045 ($864/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,053 ($579/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,704 ($529/night)
Verified & Protected
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,440 ($206/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)