Over 65 Years of Packaged Travel Leadership
Pleasant Holidays: Hawaii, Mexico & Caribbean Guide
Few travel companies in American history match the legacy and staying power of Pleasant Holidays. Established in 1959 as Pleasant Hawaiian Holidays, the company introduced millions of families and couples to the Hawaiian Islands. Today, Pleasant Holidays is a global wholesale travel giant, delivering coordinated flight, hotel, rental car, and cruise packages across the globe.
The Pleasant Holidays & Vincent Vacations Advantage
Pleasant Holidays pairs extensive buying power with Vincent Vacations, an elite agency with Signature Travel Network. When you book your vacation with our team, you access negotiated wholesale airfare, preferred Hertz car rental rates, low deposits, and Signature VIP hotel perks including daily complimentary breakfast and $100+ resort credits.
The quintessential Hawaii vacation experience, perfected by Pleasant Holidays for over 65 years.
Why Travel with Pleasant Holidays?
Booking separate flights, hotel rooms, and rental cars often leads to disjointed cancellation policies and unexpected fees. Pleasant Holidays brings everything together into one unified, guaranteed booking.
1. Unrivaled Hawaii Multi-Island Mastery
Seamlessly island-hop between Oahu, Maui, Kauai, and the Big Island. Pleasant Holidays coordinates inter-island Hawaiian Airlines flights, guaranteed Hertz rental cars, and resort stays with exclusive free nights and dining credits.
2. Comprehensive Mexico & Caribbean Resort Portfolios
From Cancun and Riviera Maya to Los Cabos, Jamaica, and Punta Cana, Pleasant Holidays contracts directly with top all-inclusive resort collections like Hyatt Inclusive Collection, Riu, Iberostar, and Outrigger Resorts.
Explore Maui's renowned Kaanapali and Wailea coasts with verified oceanfront room categories.
Sprawling lagoon pools and private cabanas bundled into vacation packages.
Top Vacation Destinations
1. The Hawaiian Islands: Oahu, Maui, Kauai & Island of Hawaii
Whether you want the cultural excitement and shopping of Honolulu, the romantic sunsets of Maui, the lush dramatic cliffs of Kauai, or the volcanic majesty of Kona, Pleasant Holidays handles every car rental, flight hop, and resort stay.
Spacious oceanfront suites with private plunge pools and 24-hour room service.
Eco-adventure packages in Costa Rica combining Arenal hot springs with Manuel Antonio beaches.
2. Central America, Tahiti & Europe
Beyond Hawaii and beach resorts, Pleasant Holidays offers custom packaging across Costa Rica, Belize, French Polynesia (Tahiti, Moorea, Bora Bora), and major European capitals.
Iconic overwater bungalows in French Polynesia bundled with Air Tahiti Nui flights.
Gourmet dining credits and private romantic beach dinners coordinated by your advisor.
Pre-book snorkeling catamarans and island tours with full supplier protection.
Sunset catamaran sails and seasonal whale watching excursions pre-reserved for your trip.
Comparing Booking Options: Self-Booking vs. Pleasant Holidays via Vincent Vacations
| Vacation Element |
Booking Separately Online |
Pleasant Holidays via Vincent Vacations |
| Rental Car Packaging |
Subject to airport vehicle shortages & surge pricing |
Guaranteed Hertz wholesale rates with free additional drivers |
| Inter-Island Flights |
Booked separately with disconnected luggage policies |
Seamless synchronized Hawaiian Airlines ticketing |
| Hotel Perks |
Standard retail rates with no added value |
Signature Travel Network breakfasts, credits & upgrades |
| Disruption Support |
Stranded managing airline and hotel cancellations alone |
Direct 24/7 advocate intervention by your personal advisor |
| Deposit Rules |
100% upfront payment required on airfare |
Low deposit options with final payment closer to departure |
Why Partner With Vincent Vacations for Pleasant Holidays?
Vincent Vacations is recognized as a premier agency partner with Pleasant Holidays:
- Signature Travel Network Consortium Perks: Daily complimentary breakfast for two, $100 resort credits, room upgrades upon availability, and VIP welcome recognition.
- Certified Hawaii & Caribbean Specialists: Our advisors provide firsthand guidance on which resorts and beaches offer the best experience for your budget.
- Complete Travel Care: If weather disruptions or airline schedule changes occur, we handle all adjustments seamlessly.
Work with an experienced Vincent Vacations advisor to maximize your Pleasant Holidays getaway.
Frequently Asked Questions About Pleasant Holidays
Founded in 1959, Pleasant Holidays is one of America's largest wholesale tour operators, renowned for its Hawaii multi-island vacations, Mexico and Caribbean all-inclusive packages, and Costa Rica getaways.
Vincent Vacations is a top agency partner for Pleasant Holidays and a member of Signature Travel Network. Booking through us provides wholesale rates, Hertz car rental perks, low deposits, and Signature VIP resort amenities.
Yes. Pleasant Holidays packages transpacific flights, inter-island Hawaiian Airlines flights, Hertz rental cars with exclusive discounts, and luxury resort stays into one coordinated reservation.
Clients enjoy complimentary daily breakfast, property credits, priority room upgrades, and 24/7 dedicated support through our agency.
Pleasant Holidays offers Comprehensive Travel Protection featuring Cancel for Any Reason cash reimbursement, price match guarantees, and emergency medical and baggage coverage.
Book Your Pleasant Holidays Vacation Today
Contact a vacation specialist at Vincent Vacations to bundle your flights, luxury resort stays, and rental cars with exclusive Signature perks.
Connect With A Vacation Specialist
Official Offices: Dallas (1341 W. Mockingbird Lane, Suite 600W, Dallas, TX 75247) & Oklahoma City (2200 W. Hefner Road, OKC, Oklahoma 73120).
