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 Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,650 ($1,950/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
Sheraton PGA Vacation Resort
Port St. Lucie, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,138 ($448/night)
Club Wyndham Nashville
Nashville, Tennessee- Dec 25–28, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/night)
Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,740 ($820/night)
Club Mykonos Langebaan
Langebaan, South Africa, Africa- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
Club Wyndham Austin
Austin, Texas- Dec 25–31, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,943 ($324/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,326 ($1,475/night)
Club Wyndham Sea Gardens
Pompano Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,738 ($1,248/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,742 ($249/night)
Morritt's The Londoner
East End, Grand Cayman, Cayman Islands- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $4,603 ($658/night)
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,362 ($766/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,944 ($1,278/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
Hilton Grand Vacations at Trump International Hotel Las Vegas
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,480 ($783/night)
Marriott's Summit Watch
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,680 ($526/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,800 ($1,257/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Massanutten's Mountainside Villas
McGaheysville, Virginia- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,996 ($1,857/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,649 ($521/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Club Wyndham Harbour Lights
San Diego, California- Dec 25–30, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,374 ($275/night)
Marriott's Harbour Lake
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,612 ($373/night)
Club Wyndham National Harbor
National Harbor, Maryland- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($315/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $8,059 ($1,151/night)
The Westin Riverfront Mountain Villas
Avon, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Grand Timber Lodge
Breckenridge, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Club Wyndham Holua Resort at the Mauna Loa Village
Kailua-Kona, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,904 ($2,129/night)
Club Wyndham Nashville
Nashville, Tennessee- Dec 25–29, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,830 ($1,404/night)
Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,930 ($704/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,206 ($744/night)
Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 25–29, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,884 ($983/night)
Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,279 ($1,611/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,990 ($1,284/night)