Christmas Timeshare Rentals in Caribbean
Celebrated each year on December 25, Christmas is the time for family traditions and festive travel. With schools and many businesses closed between Christmas Eve and New Year's Day, the holiday season is perfect for a getaway - whether you're dreaming of a snowy winter wonderland at a ski resort or a sunny beach Christmas with your loved ones!
Westwind II Club
Nassau, Bahamas- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,358 ($175/night)
Morritt's Grand Resort
East End, Grand Cayman, Cayman Islands- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,665 ($215/night)
Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,627 ($210/night)
Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($550/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,996 ($1,831/night)
Morritt's Grand Resort
East End, Grand Cayman, Cayman Islands- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,276 ($295/night)
Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($200/night)
Morritt's Grand Resort
East End, Grand Cayman, Cayman Islands- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($375/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- Studio/1 bath, sleeps 4
- $11,088 ($725/night)
Wyndham Grand Rio Mar, a Margaritaville Vacation Club Resort
Rio Grande, Puerto Rico- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,612 ($339/night)
Royal Islander Club la Plage
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,818 ($235/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,233 ($1,600/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,088 ($1,450/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,522 ($1,900/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($300/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,004 ($1,570/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,149 ($1,720/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 3 bed/5 bath, sleeps 12
- $7,274 ($950/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,832 ($630/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $5,366 ($700/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $9,944 ($1,300/night)
Morritt's The Londoner
East End, Grand Cayman, Cayman Islands- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,276 ($295/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $27,493 ($3,600/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,094 ($2,106/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,977 ($649/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,565 ($595/night)
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,996 ($1,569/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,000/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,326 ($1,350/night)
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($600/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,062 ($398/night)
Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Dec 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $545 ($70/night)
Divi Dutch Village Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,428 ($315/night)
Limetree Beach Resort by Club Wyndham
Southside, St. Thomas (USVI)- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($300/night)
Divi Dutch Village Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Divi Dutch Village Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Divi Dutch Village Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($150/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,805 ($1,675/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $27,493 ($3,600/night)
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 18–26, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $17,465 ($2,000/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($400/night)
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($639/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $14,827 ($970/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,852 ($1,550/night)
The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 10
- $9,830 ($1,285/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,200/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,045 ($920/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $28,256 ($1,850/night)