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
Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,759 ($552/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,291 ($470/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,740 ($820/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,840 ($549/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,291 ($470/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–20, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,220 ($305/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,034 ($1,576/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 16–22, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,145 ($691/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
Verified & Protected
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($359/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
Verified & Protected
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,726 ($532/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,650 ($1,093/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–22, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,598 ($766/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,090 ($1,156/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 16–22, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,854 ($476/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $995 ($142/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Verified & Protected
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,200 ($314/night)
Verified & Protected
Grand Timber Lodge
Breckenridge, Colorado- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,739 ($391/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,271 ($610/night)
Shell Island Beach Club
Sanibel Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,200 ($314/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,898 ($1,557/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,132 ($447/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,964 ($852/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)