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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,596 ($599/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,303 ($615/night)
Verified & Protected
Aspen Mountain Residences
Aspen, Colorado- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,764 ($441/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,194 ($2,028/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,281 ($326/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,510 ($1,073/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,362 ($195/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,462 ($292/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,938 ($388/night)
Verified & Protected
Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 17–22, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($768/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,220 ($244/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Long Wharf
Newport, Rhode Island- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $839 ($120/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,497 ($500/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,578 ($316/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,647 ($1,092/night)
Verified & Protected
Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–22, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($550/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,984 ($712/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,058 ($580/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $311 ($78/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,929 ($704/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,901 ($700/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 17–24, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,041 ($577/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($497/night)
Verified & Protected
Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,654 ($1,093/night)
Verified & Protected
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $577 ($115/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 17–23, 2027 (6 nights)
- 2 bed/3 bath, sleeps 6
- $6,565 ($1,094/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $471 ($118/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,015 ($1,716/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $671 ($96/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,113 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,982 ($1,140/night)