
Turn your upcoming snow days into beach days and celebrate the holidays Cayman style!
Family get-togethers can be full of stress from impressing the in-laws to last-minute holiday shopping for the season’s must-have gifts. Oh, and let’s not forget the freezing temps, wind chill factor, and snow accumulations–it’s the most wonderful time of the year!!
Leave the stress of the holidays behind and treat the whole family to a relaxing vacation under the warm Cayman sun. Give the kids holiday memories of swimming with sea turtles, or their first foray to Stingray City. Spoil yourself with some “Me-Time” lounging on the beach with a good book, or posting up by the pool with your favorite glass of wine staring off into the ocean horizon. A Cayman holiday trip is one vacation your family won’t ever forget.
Here’s a quick round up of homes with winter availability for both families and couples alike:
Pease Bay House
Looking for a home with wow factor? Pease Bay House is a gated five bedroom villa with a tennis court. Yes, you read that right–a tennis court! Gift your family tennis rackets this year and make holiday shopping a breeze! Pease Bay House continues to impress our guests with its breathtaking ocean views, beachside private pool, beautiful interiors and contemporary decor.
Available Dec. 18 – 27 and Jan. 5 – 31; Rates from $2,350 per night
Kirk Kove
Kirk Kove is the perfect couples retreat. If you’ve ever dreamed of leaving the relatives behind during the holidays, then escape to this intimate cottage for two. No offense to Grandma but everyone needs a break now and then! Stay in paradise, without breaking the bank, in this tropical getaway.
Available Dec. 1 – 26; Rates form $285 per night
Coconut Walk
Treat yourself to a luxury winter holiday you’ll remember for years to come at Coconut Walk. You’ll feel like a celebrity with airport pickup and drop-off, housekeeping services, and even plush comfy robes and slippers for a high end spa feel in your own private villa. Guaranteed to impress your mother-in-law.
Available Dec. 9 – 26 and Jan. 5 -16; Rates from $5,000 per night
Villa Zara
Ring in the New Year Cayman Style
Can’t make it to Cayman for the Christmas holiday? No worries! Come to Cayman and kick off 2019 in style. There’s no better way to start off the new year than a few weeks in paradise.

Olympus
Olympus is a modern gem perfect for a girl’s trip! Hire Perfectly Pampered for a spa day at the house, add a happy hour on the rooftop patio and you have an epic beach day to start 2019 in high style. This luxurious island getaway will make a vacation you won’t soon forget.
Available Jan. 13 – Feb. 15; Rates from $2,150 per night
Picture Perfect
Located on the South Coast, Picture Perfect has everything you need for a perfect vacation. This four bedroom villa enjoys a grassy backyard with oceanfront pool and hot tub, plus an elevated sun deck overlooking a private stretch of beach. However, the real draw to this villa is its proximity to Smith Cove, a public beach spot popular with locals for crystal clear water and great snorkeling.
Available Jan. 4 – 20; Rates from $960 per night
Villa Caymanas
On the opposite side of the island, along Old Man Bay in Northside, is Villa Caymanas. This 4 bedroom Spanish colonial villa mixes Old World charm with modern amenities from a private pool with ocean views to a home gym, and a king master suite with walk-in closet and ensuite bath. Villa Caymanas is also popular with avid snorkelers as it sits off one of the island’s more popular coral reefs, Babylon.
Available Dec. 1 – 22 and Jan. 3 – 31; Rates from $610 per night

Don’t delay planning your 2019 Cayman escape. Spring break dates are open across a majority of our villas but will fill up by February. Secret tip: Seasonal rates drop April 15th just in time for summer vacations!
Hop over to our search page to find your villa escape today!