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Winter Rentals - Enjoy the Sun and Sand

Looking to get away from the snow?

Oftentimes, winter is the best season to spend your time at the beach! There’s no need to bring along the snow gear, but maybe a warm jacket! Temperatures at the beach remain cool from November to March, but nothing compared to the freezing cold and feet of snow the North experiences every year. There are a variety of ways to enjoy your winter season with a lavish getaway  at The Caribbean Resort. From seasonal shows and events to holiday shopping and dining experiences, you will have plenty to keep you busy during your winter escape. Your monthly rental will feature all of the comforts of home, including a fully-equipped kitchen, comfortable accommodations, cable TV, WiFi Internet access, and so much more! Trade in the ice and snow for the beach and sand with your extended Winter stay at The Caribbean Resort!

Snowbirds Receive Additional Benefits:

Call us today at (866) 650-1448 and a winter rental expert will be happy to assist you!

Winter Rental Rates

Oceanfront Suite

Caribbean Dominican Oceanfront King Suite Living Room JPG
  • Oct. $1,550
  • Nov. $1,199
  • Dec. $1,199
  • Jan. $1,199
  • Feb. $1,299
  • Mar. $1,899

Chelsea 2 BR Condo

Caribbean Chelsea 2 Bedroom Deluxe Living Room 1 Scaled
  • Oct. N/A
  • Nov. $1,599
  • Dec. $1,349
  • Jan. $1,349
  • Feb. $1,549
  • Mar. N/A

Chelsea 3 BR Condo

Caribbean Chelsea Three Bedroom Deluxe Living room JPG
  • Oct. N/A
  • Nov. $1,699
  • Dec. $1,499
  • Jan. $1,499
  • Feb. $1,699
  • Mar. N/A

Angle Oceanfront 2 BR Condo

Caribbean Cayman Tower 2 Bedroom Angled Oceanfront Condo
  • Oct. $1,999
  • Nov. $1,699
  • Dec. $1,449
  • Jan. $1,449
  • Feb. $1,649
  • Mar. $2,699

Oceanfront 2 BR Condo

Caribbean Cayman 2 Bedroom Oceanfront Condo Living Room
  • Oct. $1,999
  • Nov. $1,699
  • Dec. $1,449
  • Jan. $1,449
  • Feb. $1,649
  • Mar. $2,699

Angle Oceanfront 3 BR Condo

Caribbean Cayman 3 Bedrom Angled Oceanfront Condo Master Bedroom JPG
  • Oct. $2,799
  • Nov. $1,799
  • Dec. $1,599
  • Jan. $1,599
  • Feb. $1,799
  • Mar. $2,999

Oceanfront 3 BR Condo

Caribbean Cayman 3 Bedroom Oceanfront Condo Living Room
  • Oct. $2,799
  • Nov. $1,799
  • Dec. $1,599
  • Jan. $1,599
  • Feb. $1,799
  • Mar. $2,999

Additional Winter Rental Details