Book Now

Booking Details







Special Rates

Holidays at Islander Resort

Celebrate the Islander Way

Celebrate the holiday season island-style at Islander Resort! Enjoy our special holiday offers, dining menus, and activities. 

A View Of A River

Holiday Offers 

A Vase Of Flowers Sitting On A Chair In Front Of A Fence

Tropical Togetherness Thanksgiving Package

Join us at Bayside Villas by Islander Resort to celebrate the Thanksgiving holiday with your own private Villa for up to six guests ideal for gathering with family and friends.  Plus, enjoy a 3-course Thanksgiving dinner with all the fixings served to your Villa created by our Islander Executive Chef.

Book Now

A Pool Next To A Body Of Water

Advance Purchase Offer

Plan your holiday getaway now with our Advance Purchase offer. Book your festive visit to Islander Resort to receive up to 15% off our best available rate. 

Book Now

Holiday Activities

Exciting holiday adventures for guests of Islander Resort & Bayside Villas.

A Green Boat On A Body Of Water

Sandbar with Santa, at the Islamorada Sandbar 

12/20-12/24 - 12-2pm 

Join Islander Girl Snorkel & Tours to visit Santa at the Islamorada Sandbar. Receive a complimentary framed photo to remember this special holiday moment! Limited space available. 

Call 305-712-0032 to reserve your spot. 

Adult | $85

Child (under 12 years old) | $60


Ornament Making at the Tiki Hut

Mondays at 3pm

Explore your creative side with a holiday flair with this special ornament decoration activity at the tiki hut. 


Set Sail with Santa 

December 20th-24th | 3pm-5pm 

Join us for this exciting holiday boat excursion with Santa, cookies, and a photo session. 

Price: $50 (up to 2 people per sail) 

Duration: 20 minute guided sail with Santa


Pin the star on the Christmas Tree 

December 24 at 3pm 

Join us at the Tiki Hut on Christmas Eve to pin the star onto our property’s Christmas tree. 


Paper Plate Holiday Crafts 

December 21st 3-5pm

Enjoy arts and crafts for the entire family with this paper plate festive craft activity at the Tiki Hut! 

Holiday Sale

Enjoy up to 40% off your island escape getaway with our best rates of the year.

Learn More

Sign Up for Our Newsletter