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
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,020 ($860/night)
Verified & Protected
Grand Lodge on Peak 7
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
WorldMark Scottsdale
Scottsdale, Arizona- Jan 23 – Feb 20, 2027 (28 nights)
- 1 bed/1 bath, sleeps 4
- $5,849 ($209/night)
Verified & Protected
The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,151 ($1,164/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $10,380 ($1,483/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,977 ($711/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,521 ($360/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,740 ($820/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,701 ($957/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)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/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
- $7,818 ($1,117/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)
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
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
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
Villas at Disneyland Hotel
Anaheim, California- Jan 24–27, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,125 ($375/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
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,467 ($493/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,909 ($485/night)
Verified & Protected
Villas at Disneyland Hotel
Anaheim, California- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,674 ($446/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
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
- $8,200 ($1,171/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 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
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 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)
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
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)
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
- $7,600 ($1,086/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
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/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
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
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 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
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
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)