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.
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Hilton Grand Vacations at the Flamingo
Las Vegas, Nevada- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,434 ($205/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,579 ($940/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–8, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Pono Kai
Kapaa, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,769 ($253/night)
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 4–11, 2026 (7 nights)
- 1 bed/3 bath, sleeps 8
- $2,478 ($354/night)
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,358 ($194/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,780 ($254/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Westgate Town Center
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,009 ($287/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–7, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $832 ($278/night)
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $971 ($139/night)
WorldMark Kona Resort
Kailua-Kona, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,849 ($264/night)
Lagonita Lodge
Big Bear Lake, California- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $971 ($139/night)
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,742 ($249/night)
Grandview at Las Vegas
Las Vegas, Nevada- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,126 ($161/night)
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 4–12, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($752/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,619 ($374/night)
Grand Timber Lodge
Breckenridge, Colorado- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($284/night)
Wyndham La Cascada
San Antonio, Texas- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,742 ($249/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
The Westin Kierland Villas
Scottsdale, Arizona- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,473 ($782/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,467 ($352/night)
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 4–10, 2026 (6 nights)
- 2 bed/3 bath, sleeps 6
- $5,312 ($885/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,543 ($363/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,588 ($227/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,505 ($358/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,676 ($525/night)
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 5–10, 2026 (5 nights)
- 1 bed/1 bath, sleeps 6
- $4,925 ($985/night)
Seawatch On-the-Beach Resort
Fort Myers Beach, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,994 ($285/night)
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Dec 5–10, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,082 ($216/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,268 ($467/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 5–13, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $848 ($106/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($625/night)
Grand Colorado on Peak 8
Breckenridge, Colorado- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)