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 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/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 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/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 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
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 #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
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
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
Hyatt Beach House Resort
Key West, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/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 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
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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/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
- $10,924 ($1,561/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 6
- $746 ($249/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 17–25, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,446 ($306/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($731/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–25, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,251 ($156/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/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
- $1,637 ($546/night)
Verified & Protected
Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 18–21, 2027 (3 nights)
- Studio/1 bath, sleeps 2
- $1,442 ($481/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 6
- $2,039 ($291/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
Vista Encantada Spa Resort & Residences
Cabo San Lucas, Mexico- Jan 18–25, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 18–29, 2027 (11 nights)
- 2 bed/2 bath, sleeps 6
- $2,965 ($270/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
- $6,238 ($891/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 18–22, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($769/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)
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 18–22, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($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
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)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 18–23, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,711 ($542/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,833 ($1,405/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)
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 8
- $1,194 ($298/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
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 18–23, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,396 ($279/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
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
CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 18–22, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $247 ($62/night)