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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $603 ($201/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $746 ($249/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $804 ($201/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
- $2,576 ($515/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,902 ($484/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,802 ($467/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
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)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/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
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($332/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($249/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $995 ($249/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
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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,194 ($298/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–21, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,995 ($714/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $896 ($299/night)
Verified & Protected
Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
Verified & Protected
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($359/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
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,619 ($524/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
The Ritz-Carlton Club, Lake Tahoe
Truckee, California- Jan 18–25, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $14,195 ($2,028/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,874 ($696/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 18–22, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,327 ($582/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–22, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $995 ($249/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–22, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,802 ($829/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 18–31, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,746 ($211/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,963 ($423/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 18–22, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,188 ($547/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–22, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $804 ($201/night)
WorldMark Steamboat Springs Resort
Steamboat Springs, Colorado- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–22, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($249/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 18–23, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)