Fireworks over New York City
Festive Christmas lights on piƱata and building in mexico
Couple with santa hats on Caribbean beach
Ice skaters at night in European Christmas Market

Holiday Season Vacations & Celebrations

This year, start a new tradition – mark a special occasion with vacation to remember. Celebrate an enduring romance, mark a milestone birthday, honor a special person, welcome new beginnings, or immerse yourself in a new culture. Travel is a great way to connect with family and friends, embrace unique experiences and create holiday vacation memories to last all year round.
New Year's Fireworks in Las Vegas

USA Holiday Season Vacations

Ring in the new year in Las Vegas; trade in a traditional Thanksgiving with theme park thrills; spend winter break on the slopes or with a warm drink enjoying the sparkling beauty of a mountain resort. The possibilities are endless.

Festive holiday flags on Mexican church

Mexico Holiday Season Vacations

The holiday season in Mexico means three weeks of festivals, religious events and traditional foods to enjoy. Combine it with balmy winter weather for the perfect family getaway.

Maui Beach at Sunset

Hawaii Holiday Season

Experience the joy and festivities of the holiday season, and save on vacations to Oahu, Maui and Kauai with exclusive offers only available through Pleasant Holidays.

Woman in Santa hat on Caribbean beach

Christmas in the Caribbean

Celebrate the old and welcome in the new in the Caribbean, with street parties that stretch into the night and unique foods and gifts available at no other time of year.

Tahiti Beach

Tahiti Holiday Season

Spend a relaxing winter vacation in paradise on the Islands of Tahiti. Elevate your experience with a stay in an overwater villa for a vacation  unlike any other.