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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 Deluxe Suite

Oceanfront Deluxe One Bedroom Double Suite
  • Oct. $1,674
  • Nov. $1,261
  • Dec. $1,261
  • Jan. $1,261
  • Feb. $1,361
  • Mar. $2,085

Oceanfront Suite

Oceanfront King Suite
  • Oct. $1,550
  • Nov. $1,199
  • Dec. $1,199
  • Jan. $1,199
  • Feb. $1,299
  • Mar. $1,899

Chelsea Deluxe Two Bedroom Condo

Caribbean Chelsea 2 Bedroom Deluxe Living Room 1 Scaled
  • Oct. $1,880
  • Nov. $1,416
  • Dec. $1,416
  • Jan. $1,416
  • Feb. $1,516
  • Mar. $2,302

Ocean View Two Bedroom Condo

Caribbean Cayman Tower 2 Bedroom Angled Oceanfront Condo
  • Oct. $2,046
  • Nov. $1,571
  • Dec. $1,571
  • Jan. $1,571
  • Feb. $1,671
  • Mar. $2,519

Oceanfront Deluxe Two Bedroom Condo

Oceanfront Deluxe Two Bedroom Condo
  • Oct. $2,356
  • Nov. $1,726
  • Dec. $1,726
  • Jan. $1,726
  • Feb. $1,826
  • Mar. $2,984

Oceanfront Two Bedroom Condo

Caribbean Cayman 2 Bedroom Oceanfront Condo Living Room
  • Oct. $2,232
  • Nov. $1,664
  • Dec. $1,664
  • Jan. $1,664
  • Feb. $1,764
  • Mar. $2,798

Chelsea Three Bedroom Condo

Caribbean Chelsea Three Bedroom Deluxe Living room JPG
  • Oct. $2,542
  • Nov. $1,881
  • Dec. $1,881
  • Jan. $1,881
  • Feb. $1,981
  • Mar. $3,201

Ocean View Deluxe Three Bedroom Condo

Ocean View Deluxe Three Bedroom Condo
  • Oct. $2,852
  • Nov. $2,098
  • Dec. $2,098
  • Jan. $2,098
  • Feb. $2,198
  • Mar. $3,604

Ocean View Three Bedroom Condo

Caribbean Cayman 3 Bedrom Angled Oceanfront Condo Master Bedroom JPG
  • Oct. $2,728
  • Nov. $2,036
  • Dec. $2,036
  • Jan. $2,036
  • Feb. $2,136
  • Mar. $3,418

Oceanfront Deluxe Three Bedroom Condo

Oceanfront Deluxe Three Bedroom Condo
  • Oct. $3,038
  • Nov. $2,191
  • Dec. $2,191
  • Jan. $2,191
  • Feb. $2,291
  • Mar. $3,883

Oceanfront Three Bedroom Condo

Oceanfront Three Bedroom Condo
  • Oct. $2,914
  • Nov. $2,129
  • Dec. $2,129
  • Jan. $2,129
  • Feb. $2,229
  • Mar. $3,697

Oceanfront Deluxe Three Bedroom Corner Condo

Oceanfront Deluxe Three Bedroom Corner Condo
  • Oct. $3,100
  • Nov. $2,222
  • Dec. $2,222
  • Jan. $2,222
  • Feb. $2,322
  • Mar. $3,976

Oceanfront Three Bedroom Corner Condo

Oceanfront 3 bedroom corner condo
  • Oct. $3,224
  • Nov. $2,284
  • Dec. $2,284
  • Jan. $2,284
  • Feb. $2,384
  • Mar. $4,162

Oceanfront Deluxe Four Bedroom Condo

Oceanfront Deluxe Four Bedroom Condo
  • Oct. $3,534
  • Nov. $2,501
  • Dec. $2,501
  • Jan. $2,501
  • Feb. $2,601
  • Mar. $4,565

Oceanfront Four Bedroom Condo

Oceanfront Four Bedroom Condo
  • Oct. $3,410
  • Nov. $2,439
  • Dec. $2,439
  • Jan. $2,439
  • Feb. $2,539
  • Mar. $4,379

Additional Winter Rental Details