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.
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)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/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)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,121 ($1,017/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 Kauai Beach Club
Lihue, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,711 ($673/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/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)
Villas at Disneyland Hotel
Anaheim, California- Dec 25–27, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,985 ($992/night)
Club Wyndham Austin
Austin, Texas- Dec 25–29, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,163 ($291/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)
The Pointe on the Bay
Ocean City, Maryland- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $1,932 ($276/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,204 ($172/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,467 ($638/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)
Grand Luxxe at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $6,785 ($969/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)
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)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/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)
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)
Club Wyndham Resort at Avon
Avon, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/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)
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)
Westgate Vacation Villas
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,314 ($331/night)
Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,145 ($592/night)
The Ritz Carlton Club, San Francisco
San Francisco, California- Dec 25–28, 2026 (3 nights)
- 1 bed/1.5 bath, sleeps 4
- $2,478 ($826/night)
Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,165 ($166/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Dec 25–29, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $790 ($198/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)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Dec 25–31, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($216/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)
Club Wyndham Flagstaff
Flagstaff, Arizona- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Kahana Villa Resort
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, 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
- $3,710 ($530/night)
Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Dec 25, 2026 – Jan 3, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($221/night)
Hurricane House
Sanibel Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,328 ($761/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/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)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)