Upgrade Your Winter Holiday Plans

Home view of Caribbean Sea and pool.
Pease Bay House’s backyard views of the Caribbean Sea.

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

Paradise awaits at . This seaside mansion retreat has four bedrooms and gorgeous interiors. Head to the Famous Rum Point just a short walk from your villa. Perfect for families or friends looking for a tropical winter getaway to escape cold days.
Available Dec. 11 – 26 and Jan. 4 – 31; Rates from $1,100 per night

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 Villa during a stunning sunset.
Stunning Cayman sunset reflecting off 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

Villa Caymanas
Old World charm meets chic island living at Villa Caymanas


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!