Save On Hawaii Hotels With Pleasant Holidays

Start planning your Hawaii Vacation for late 2020.

Book by Jul 31, 2020

Time for Hawaii!

The Hawaiian Islands are slices of paradise in the Pacific, a lush archipelago of hundreds of islands stretching across 1,500 breathtaking miles. Only six of these majestic isles, Kauai, Oahu, Molokai, Lanai, Maui, and the Island of Hawaii (popularly known as “The Big Island”) are currently open to the public.

Book Now for the Guaranteed Lowest Hotel Rates for 2020 when you book a Hawaii Package Vacation1 


Exclusive Bonuses when you book with Pleasant Holiday airfare! Bonuses may include

• Exclusive Reduced Room Rates

• FREE Breakfast, Resort Credit or Food & Beverage Credit

• Savings on Spa Treatments and more!



Our Recommended Hotel Stays

Moana Surfrider, A Westin Resort & SpaDec 01, 2020 - Dec 05, 2020 (5 nights)

Oahu, Waikiki Beach | Historic Banyan Room
USD $993 Per Person Incl taxes
INCLUDES: Lei Greeting & Moana Elixir upon arrival.

Celebrate the best of Honolulu from Moana Surfrider, A Westin Resort & Spa, Waikiki Beach. Widely known as the "First Lady of Waikiki," this historic hotel first opened its doors in 1901 and offers a seamless blend of Victorian elegance and contemporary comfort. Boasting an unbeatable beachfront location, just steps from the immaculate shores of legendary Waikiki Beach and within walking distance of Honolulu's most beloved shopping, dining and entertainment attractions. For your convenience, we provide three distinct, sophisticated room layouts, each one overflowing with thoughtful amenities. In addition, our hotel features a towering banyan tree, a shimmering outdoor pool, a state-of-the-art fitness center, the only beachfront spa in Waikiki and six on-site bars and restaurants.

Sheraton Maui Resort & SpaDec 01, 2020 - Dec 05, 2020 (5 nights)

Maui | Resort View Double
USD $989 Per Person Incl taxes
INCLUDES: Kids 17 & younger stay FREE.

Located on 23 lush oceanfront acres at legendary Pu‘u Keka‘a on Ka‘anapali Beach, Sheraton Maui Resort & Spa invites travelers to experience adventure, romance and family fun on the island of Maui. Relax at the resort’s 142-yard lagoon style pool, taste fresh island cuisine, learn indigenous Hawaiian cultural activities and play at the white sandy beach. Eighty-three percent of the resort’s 508 rooms and suites feature breathtaking views of the Pacific, and sister islands Lanai and Molokai. At sunset, the resort showcases its iconic cliff dive ceremony, a tradition since the resort first opened in 1963. Make lasting memories as you unwind during sunset, snorkel with tropical fish and honu (green sea turtles), learn ukulele with family or rejuvenate at The Spa at Black Rock.

Sheraton Kauai ResortDec 01, 2020 - Dec 05, 2020 (5 nights)

Kauai | Deluxe Garden View
USD $871 Per Person Incl taxes
INCLUDES: Kids 17 & younger stay FREE.

Welcome to an oasis nestled on the world-famous Poipu Beach. From this enviable vantage point, this hotel offers guests intimate access to the Garden Island's endless charms—from spectacular beaches to lush rainforests to world-class golf courses. Relax innewly-renovated guest rooms and suites, where either sparkling oceanfront or lush garden views await. Spend your days soaking in the sun on Poipu Beach or relaxing in a shaded cabana next to the Ocean Pool. Dine at an array of authentic eateries, serving fresh Hawaiian fare in a tropical setting; RumFire Poipu Beach is the signature restaurant boasting spectacular sunset views. Whatever brings you to Kauai, the golden-sand beaches and misty sea breezes will ensure you'll never want to leave.

The Westin Hapuna Beach ResortDec 01, 2020 - Dec 05, 2020 (5 nights)

Kohala Coast, Hawaii | Partial Ocean View
USD $877 Per Person Incl taxes
INCLUDES: Includes 5th night FREE PLUS Kids 17 & younger stay FREE.

The Westin Hapuna Beach Resort stretches along its namesake white-sand beach on the Island of Hawaii. The Kohala Coast is known for its world-class shoreline as well as for the cultural and archaeological gems nestled between its centuries-old lava fields. The resort’s contemporary style contrasts with the lush, manicured gardens and the endless blues of the sky and the ocean. Enjoy four reimagined dining venues influenced by the island’s bounty. Hit the links on the award-winning 18-hole Hapuna Golf Course designed by Arnold Palmer. Cool off in two swimming pools, including a 6,800-square-foot freeform family pool and an adult-exclusive infinity pool, overlooking Hapuna Beach. The WestinWorkout Center and Crossfit Studio are complemented by the Hapuna Spa for rejuvenation and relaxation. You can choose from 249 oversized guest rooms, including 17 suites.

Whether you are interested in a luxury getaway or a budget vacation, looking for romance or adventure, or wanting to travel far or stay close to home. Five-star resort and all-inclusive getaways, adult-only-escapes or family-friendly vacations. Pleasant Holidays has everything you need at the value you want to the places you want to explore!  

Terms & Conditions

1 Rate is per person, land only, based on double occupancy for check-in on 12/01/2020, in room categories shown. Unless otherwise indicated: rates quoted are accurate at time of publication, & are per person, based on double occupancy. Airfare, taxes, surcharges, gratuities, transfers & excursions are additional. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel at check-out; such fee amounts will be advised at the time of booking. Rates, terms, conditions, availability, itinerary, government taxes, surcharges, deposit, payment, cancellation terms/conditions & policies subject to change without notice at any time. Cruise rates capacity controlled. Other restrictions may apply, including, but not limited to baggage limitations & fees, standby policies & fees, non-refundable tickets & change fees with pre-flight notification deadlines, & blackout dates. Fees & policies vary among airlines. Contact airline directly for any details or questions. Not responsible for errors or omissions. Pleasant Holidays acts only as an agent for cruise & tour providers listed. CST# 1007939-10. Copyright©2020 Pleasant Holidays, LLC. All Rights Reserved.