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
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
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,758 ($460/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($551/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
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
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 24–26, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $981 ($491/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
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/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
- $1,098 ($220/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
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,379 ($476/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 25–29, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,118 ($529/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 25–29, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $247 ($62/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 25 – Feb 2, 2027 (8 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($344/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham South Shore
Zephyr Cove, Nevada- Jan 25–29, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($249/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 25–29, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $471 ($118/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 25 – Feb 2, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,870 ($234/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Nashville
Nashville, Tennessee- Jan 25–29, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $311 ($78/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham South Shore
Zephyr Cove, Nevada- Jan 25–29, 2027 (4 nights)
- 3 bed/2 bath, sleeps 8
- $1,207 ($302/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 25–29, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $471 ($118/night)
WorldMark Steamboat Springs Resort
Steamboat Springs, Colorado- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,292 ($899/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 25–29, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $710 ($178/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 25 – Feb 1, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,734 ($1,248/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 25 – Feb 3, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $3,786 ($421/night)
Verified & Protected
Club Wyndham Riverside Suites
San Antonio, Texas- Jan 25–29, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $343 ($86/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 25–29, 2027 (4 nights)
- 3 bed/2 bath, sleeps 8
- $995 ($249/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 26 – Feb 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 26–29, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($1,316/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 26 – Feb 1, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($531/night)
Verified & Protected
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Jan 26–30, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $555 ($139/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 26–31, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,743 ($549/night)
Verified & Protected
Daytona SeaBreeze
Daytona Beach, Florida- Jan 26–31, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $999 ($200/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 27 – Feb 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,914 ($416/night)
Verified & Protected
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 27 – Feb 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,204 ($315/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 27 – Feb 2, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,795 ($299/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 27 – Feb 6, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,607 ($161/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 27 – Feb 6, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,399 ($240/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 27 – Feb 6, 2027 (10 nights)
- 3 bed/2 bath, sleeps 10
- $2,924 ($292/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 27 – Feb 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 27 – Feb 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,475 ($246/night)