Christmas Programming

Make memories for a lifetime this holiday at Villas of Grand Cypress Orlando. This season we are offering a fun-filled, jam packed activities schedule with something for every member of the family. 

Holiday Programming: 
Weekend Events November 29 – December 20 
Daily Events December 21 – January 3


10:00 am to 12:00 pm | 3:00 pm to 5:00 pm

Calling all potential elves! Santa is extra busy this year and he needs your help. The Villas of Grand Cypress Elves-In-Training Program will teach you all you need to know to make it on the North Pole.

Holiday Programming: 
Weekends November 29 – December 20 
Daily December 21 – January 3

Hot Cocoa Happy Hour

1:30 pm to 3:30 pm

Nothing says holiday time like a cup of hot chocolate, even when it’s 70 degrees out. Join us poolside during Hot Cocoa Happy Hour for buy one, get one cocoa and a cookie for only $3. If you get too hot drinking this chocolaty treat, then jump into the pool for a perfect 84 degree dip. 

Holiday Programming:       
Weekends November 29 – December 20          
Daily December 21 – January 3

Holiday Story Telling

2:00 pm to 3:00 pm

Join us at the pool for a traditional holiday story. Learn why the Grinch stole Christmas, find out if Frosty melts, and discover what really happened the night before Christmas. 

Holiday Programming:
Weekends November 29 – December 20 
Daily December 21 – January 3

Family Style Dessert

6:00 pm to 8:00 pm

Join us for dinner in The Club or Nine18 between 6pm and 8pm and we’ll provide a complimentary chef-selected family style dessert with plenty of sweet goodness for each member of the family that consumed an entree. 

Holiday Programming:
Weekends November 29 – December 20 
Daily December 21 – January 3

Poolside Holiday Movies & We Want S'More

Saturdays December 20 - January 3 | 7:00 pm

Gather around the resort's poolside firepits to enjoy the irresistible combination of fresh Florida breezes, crunchy graham crackers, toasty marshmallows, and warm gooey chocolate--the perfect recipe for family togetherness or romantic alone time. Catch your favorite holiday movies playing poolside on the "big screen!"

Breakfast With Santa

Sunday December 21 | 8:00 am to 10:00 am

Join Santa for breakfast at the Club. Bring a toy for Toys for Tots and save $5 off per person* for each toy donated. Breakfast will be served family style and based on the following price scale:

  • Adults $22.95
  • Kids 13 and under $15.95
  • Kids 2 and under complimentary

'Twas the Night Before Christmas

Tuesday December 23 | 6:00 pm to 8:00 pm

Deck the halls and jingle your bells; this is NOT going to be a silent night! Join in the fun as we gather together for holiday trivia, hot chocolate, and caroling to spread holiday cheer. Oh what fun it is to sing...with an evening of Christmas caroling. 

Retired Elf Program & Gift Wrap Station

Tuesday December 23

Learn how to make (and drink) festive holiday cocktails and nibble on savory seasonal tapas while you get your gift wrapping done in time for the big day!

Christmas Dinner

Thursday December 25 | 11:00 am to 10:00 pm

Join us from 11:00 am  to 10:00 pm in the Club and 1:00 pm to 10:00 pm in Nine18 for our gourmet holiday feast, featuring a Key West lobster risotto, a holiday spice marinated rib eye pave, all the trimmings, and an extra special holiday chestnut fig cake. Pricing for Christmas dinner is $55 per adult and $25 per child.

Click Here to see our Holiday Menu.