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!
Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Dec 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $614 ($79/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,516 ($1,375/night)
Wyndham Grand Rio Mar, a Margaritaville Vacation Club Resort
Rio Grande, Puerto Rico- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,288 ($499/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($320/night)
Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($700/night)
Eagle Aruba Resort
Oranjestad, Aruba- Dec 20–27, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $6,015 ($785/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,083 ($925/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21, 2026 – Jan 4, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $17,376 ($1,137/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($450/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,663 ($870/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,715 ($1,401/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($375/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,001 ($390/night)
Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,757 ($227/night)
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($850/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,794 ($625/night)
Paradise Island Beach Club
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,039 ($395/night)
Casa del Mar Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($300/night)
Morritt's Grand Resort
East End, Grand Cayman, Cayman Islands- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,238 ($290/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
- $4,984 ($650/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,500/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($850/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $9,486 ($620/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,522 ($1,900/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,100/night)
Windjammer Landing Villa Beach Resort
Castries, St. Lucia- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($450/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,503 ($849/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,595 ($599/night)
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $15,558 ($2,036/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,963 ($385/night)
Oyster Bay Beach Resort
Philipsburg, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Dec 20, 2026 – Jan 16, 2027 (27 nights)
- 2 bed/2 bath, sleeps 8
- $14,151 ($480/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,100/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,379 ($1,357/night)
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $12,653 ($1,655/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,426 ($970/night)
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,824 ($760/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,382 ($440/night)
Barcelo Aruba
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,993 ($520/night)
Barcelo Aruba
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,298 ($429/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,723 ($1,140/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,936 ($1,299/night)
The Crane, a Hilton Grand Vacations Club
St. Philip, Barbados- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($350/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
- $2,619 ($340/night)
Barcelo Aruba
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,565 ($595/night)
Barcelo Aruba
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,306 ($430/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,888 ($2,079/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($300/night)
Hyatt Hacienda Del Mar
Dorado, Puerto Rico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($600/night)