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
WorldMark Steamboat Springs Resort
Steamboat Springs, Colorado- Jan 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 12–17, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,096 ($419/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 13–18, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($833/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 13–17, 2027 (4 nights)
- 3 bed/3 bath, sleeps 10
- $4,385 ($1,096/night)
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 14–24, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($275/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,711 ($673/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 14–19, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $1,932 ($386/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,531 ($362/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($660/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,545 ($1,078/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,015 ($1,716/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,045 ($1,006/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,015 ($1,716/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,268 ($467/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,471 ($412/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,919 ($703/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,083 ($298/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,974 ($1,568/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,038 ($720/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–20, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $5,475 ($1,095/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 15–17, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $870 ($435/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 15–22, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $20,735 ($2,962/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 15–22, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $16,811 ($2,402/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,321 ($554/night)
Verified & Protected
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 15–19, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,255 ($564/night)