Why Pleasant Holidays?

Trust your vacation planning to the experts. They’ve been providing unforgettable, one-of-a-kind vacation packages for 60 years. What’s more, thier US-based travel advisors are passionate about travel, and are readily available to help us help you, before, during and after your trip.

Book Hawaii with the Experts

• Voted Best Tour Operator Hawaii 15 Consecutive Years
• Lowest Hawaii Hotel Rates & Added Values at Oceanfront Resorts on 4 Islands
• Most Competitive Private Fares on Major Airlines to Hawaii & Inter Island Flights
• First Class & Premium Economy Seating Flight Options
• 60 Certified Hawaii Destination Specialist Reservations Agents
• 200+ Hotels, Condos, Villas & Private Homes on 6 Islands
• 900+ Hawaii Sightseeing Tours, Events & Luaus with Premium Seating
• NCL Hawaiian Islands Cruises Year-Round Honolulu & Pre/Post Stay Options
• Exclusive Hertz Check-In at Hawaii Airport Locations
• Fresh Flower Lei Greetings at Hawaii Airport Locations Available

Best Price Guarantee

At Pleasant Holidays, you'll find friendly, knowledgeable service is complemented by a commitment to providing our customers with great value. Which is why, if you find a lower price on the same vacation package elsewhere, they'll match it!

Vacations Your Way

 Whether you're planning a luxury getaway or travel on a shoestring budget, you're in the mood for romance or adventure, or you want to travel across the world or around the bend. From five-star resorts and all-inclusive options to villas and fully equipped condominiums with the conveniences of home, from adults-only-escapes to family-friendly getaways, from urban oasises to sprawling jungle resorts, your Pleasant Holidays vacation can be anything you want it to be.

The strength of our partnerships allows us to offer you greater value. Free nights, exclusive savings, free breakfast offers, free car rentals, room or car rental upgrades, and special amenities are possibilities. 

Everything You Need, All In One Place

Pleasant Holidays offer flights, hotels and vacation rentals, car rental and airport transfer options, sightseeing tours and activities as well as travel protection – all in one place.

Bundle your vacation for lower pricing than when you purchase the individual components of your trip separately. That's because we negotiate special deals with our suppliers that help you save more.