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!
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,022 ($786/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,266 ($949/night)
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2.5 bath, sleeps 6
- $30,545 ($2,000/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
- $15,830 ($2,071/night)
Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $932 ($120/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,657 ($345/night)
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $33,815 ($2,214/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $26,620 ($1,743/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21, 2026 – Jan 4, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $26,730 ($1,750/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,614 ($1,650/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,090 ($1,057/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,647 ($999/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)
Sea Palace Resort
Philipsburg, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,358 ($175/night)
Divi Dutch Village Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($375/night)
Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,919 ($510/night)
Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($500/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,276 ($295/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,532 ($1,115/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,746 ($1,143/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $5,290 ($690/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,968 ($910/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,314 ($300/night)
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,846 ($1,025/night)
Eagle Aruba Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,200 ($285/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,314 ($300/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($500/night)
Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,679 ($610/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,039 ($395/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
- $2,505 ($325/night)
The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($650/night)
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($743/night)
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,269 ($949/night)
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($429/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,361 ($1,486/night)
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $7,056 ($921/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 Aruba Surf Club
Palm Beach, Aruba- Dec 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $10,379 ($1,357/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,350 ($829/night)
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $22,915 ($3,000/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
- $5,366 ($700/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,742 ($225/night)
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 18–26, 2026 (8 nights)
- 1 bed/2 bath, sleeps 4
- $3,504 ($399/night)
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,688 ($349/night)
Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $699 ($90/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,742 ($225/night)
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,549 ($855/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,076 ($400/night)