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
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
Verified & Protected
Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,759 ($552/night)
Verified & Protected
The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,746 ($249/night)
Verified & Protected
Caribbean Palm Village
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($253/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–28, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($715/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,065 ($516/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 24–29, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,527 ($505/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,440 ($888/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($625/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($477/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–27, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,436 ($479/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $2,739 ($548/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,739 ($963/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,458 ($494/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,604 ($434/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,090 ($1,156/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–28, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($633/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,944 ($1,421/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,214 ($243/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($611/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 24 – Feb 7, 2027 (14 nights)
- 3 bed/2 bath, sleeps 8
- $6,565 ($469/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 24–30, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $6,666 ($1,111/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–31, 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 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)