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
Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Jan 4–11, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,290 ($1,327/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,584 ($798/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,058 ($580/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,832 ($1,405/night)
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WorldMark Park City
Park City, Utah- Jan 4–11, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $6,129 ($876/night)
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Paradise Village Beach Resort & Spa
Nuevo Vallarta, Mexico- Jan 4–12, 2027 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($439/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,982 ($1,140/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 5–12, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,640 ($377/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Jan 5–9, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,093 ($1,156/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,083 ($1,012/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,034 ($719/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 5–11, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,234 ($539/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,854 ($979/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,651 ($530/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,492 ($498/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 9
- $9,276 ($1,855/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,001 ($600/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,466 ($693/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,933 ($587/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 6–12, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,565 ($1,094/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 6–10, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,100 ($525/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,466 ($693/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,996 ($599/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,965 ($593/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,933 ($587/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 6–10, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,188 ($547/night)
Verified & Protected
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 6–12, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,334 ($556/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,091 ($1,156/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 7–12, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
Verified & Protected
The Villas at Disney's Grand Californian Hotel & Spa
Anaheim, California- Jan 7–10, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $2,020 ($673/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 7–11, 2027 (4 nights)
- 1 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Verified & Protected
Villa La Estancia Cabo San Lucas
Cabo San Lucas, Mexico- Jan 7–10, 2027 (3 nights)
- 2 bed/3 bath, sleeps 6
- $2,096 ($699/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,218 ($1,031/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,987 ($855/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 8–12, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,188 ($547/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Jan 8–22, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $4,058 ($290/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,001 ($429/night)
Verified & Protected
Eagle's Nest Beach Resort
Marco Island, Florida- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Sheraton Mountain Vista Villas
Avon, Colorado- Jan 8–12, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,760 ($440/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)