Save On Hawaii Hotels With Pleasant Holidays

Start planning your Hawaii Vacation for 2020.

Book by Dec 31, 2019

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 Reduced Room Rates

• FREE Breakfast, Resort Credit or Food & Beverage Credit

• Up to 15% Savings on Spa Treatments and more!



Our Recommended Hotels 

Grand Wailea Maui2May 18, 2020 - May 23, 2020 (5 nights)

Maui | Run of House
USD $1,983 Per Person Incl taxes
INCLUDES: Exclusive room rate and $15 per person per day resort credit PLUS 15% savings on spa treatments!

Embark on a vacation like never before with 40 acres of lush tropical gardens and endless activities to choose from – the ultimate destination for an immersive Hawaiian getaway. With an endless supply of activities, adventures and excitement, there’s a reason Grand Wailea is consistently ranked among the world’s best resorts by leading travel consumer reports and industry peers.

Sheraton Maui Resort & Spa3May 18, 2020 - May 23, 2020 (5 nights)

Maui | Resort View
USD $1,403 Per Person Incl taxes
INCLUDES: Exclusive room rate, $30 dining credit per day valid at ROCKsalt and extra person fee waived–valued at up to $200 per night!

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.

Moana Surfrider, A Westin Resort & Spa4May 18, 2020 - May 23, 2020 (5 nights)

Oahu, Waikiki Beach | Banyan City
USD $1,335 Per Person Incl taxes
INCLUDES: Exclusive room rate; daily Moana Beach Club access for two with light breakfast; light midday snack and SuperFoodsRX™ elixir; and evening pupus, wine and beer5, soft drinks and more; PLUS 15% savings on spa treatments!

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 Kona Resort & Spa at Keauhou Bay6May 18, 2020 - May 23, 2020 (5 nights)

Kailua-Kona | Mountain View
USD $1,035 Per Person Incl taxes
INCLUDES: Exclusive room rate and daily continental breakfast buffet for two PLUS 15% savings on spa treatments!

With an unmatched location on the iconic lava rocks of the Big Island's Kona Coast, Sheraton Kona Resort & Spa at Keauhou Bay offers a captivating blend of adventure, culture, heritage and authentic Hawaiian hospitality. Nestled atop the lava rock cliffs of the Kona Coast, our ocean side retreat overlooks Keauhou's giant manta ray coastal feeding grounds and is minutes from Kona Coffee farms, a short drive from snorkeling in Kealakekua Bay and the closest resort to Volcanoes National Park. Embrace island life in our oceanfront pool, at Ho'ola Spa, or via watersports and traditional Hawaiian activities, such as snorkeling in the bay, cultural tours, and hula lessons.

Kaua'i Marriott Resort7May 18, 2020 - May 23, 2020 (5 nights)

Lihue | Pool View
USD $1,300 Per Person Incl taxes
INCLUDES: Exclusive reduced rates, $50 food & beverage credit per room for stays of 1-4 nights or $100 food & beverage credit per room for stays of 5 nights or longer PLUS 10% savings on spa treatments!

Come to Kaua’i, the Garden Island of Hawaii, and treat yourself to breathtaking bay views & beachside fun at Kaua'i Marriott Resort. Ideally set in Lihue, just 2 miles from the airport, this stylish, contemporary resort hotel features top-tier amenities and modern rooms and suites with panoramic ocean, garden or pool views. Dine on-site at five restaurants. Bask in the sun, surf in the bay or float around in the largest one-level outdoor pool in Hawaii. Workout on your own schedule in our 24-hour fitness center or book a pampering spa treatment or massage. Avid golfers return again and again to meet the challenge of our Jack Nicklaus signature golf course, the longest in Hawaii. Our resort on beautiful Kalapaki Bay is also an ideal location for bachelorette parties and destination weddings. Whatever brings you to our island, we look forward to welcoming you with the spirit of Aloha.

Terms & Conditions

1Guaranteed Lowest Hotel Rates for 2020 Hawaii Package Vacations: All offers require inclusion of roundtrip transpacific air and accommodations. Certain restrictions apply. All offers and programs are subject to availability, change or cancellation without notice. Blackout dates may apply. 2Grand Wailea Package: Requires Run of House or Run of Ocean accommodations. Resort credit is $15 per paying adult per day, which will be posted to guest incidental account; no cash refund will be given for any unused resort credit. Resort credit may be applied towards food and beverage at any Grand Wailea restaurants including Café Kula, Spa Treatment, Resort Charge, Parking and Grand Wailea retail outlets. Valid on new bookings for travel 1/4/20 – 12/24/20. 3Sheraton Maui Resort & Spa Package: Requires Resort View or Ocean View accommodations. Offer applies to a limited number of rooms and is based on availability. Value of extra person fee waiver is based on two additional guests staying in same room using existing bedding. Valid on new bookings for travel 1/4/20 – 1/3/21. 4Moana Surfrider, A Westin Resort & Spa Package: Requires Banyan City, Tower City or Diamond Ocean accommodations. Valid on new bookings for travel 1/3/20 – 1/2/21. 5Age restrictions may apply. 6Sheraton Kona Resort & Spa at Keauhou Bay Package: Requires Mountain View or Ocean View accommodations. Valid on new bookings for travel 1/3/20 – 1/4/21. 7Kauai Marriott Resort Package: Requires Pool View or Ocean View accommodations. Food & beverage credit valid at Kukui’s on Kalapaki Beach, Aupaka Terrace or Toro Tei Sushi Bar. Credit may not be applied toward room rate, tax, resort fee, parking or any other charges. Unused credits are non-refundable and have no cash value. Spa and salon services must be booked upon arrival. Valid on new bookings for select travel 1/3/20 – 1/2/21. *Rate is per person, based on double occupancy, for check-in on 5/18/2020, in room categories listed, & includes roundtrip coach air transportation from YYZ as shown. See General Disclaimer for terms and conditions of air-inclusive offer. General Disclaimer for All Offers. Unless otherwise indicated: rates quoted are accurate as of November 2, 2019, are per person, based on double occupancy and are for the lowest accommodation category. Gratuities, transfers & excursions are additional. Advertised rates are subject to additional taxes and surcharges, however, such amounts, if collected by Pleasant Holidays, are included in land-only and air-inclusive advertised rates. Daily resort or facility fees payable directly to the hotel at check-out may apply; such fee amounts are excluded from advertised rates and will be advised at the time of booking. Rates may not be available on all travel dates. Airline tickets may be non-refundable. Additional restrictions may apply, including, but not limited to, baggage charges for first and/or second checked bag, advance purchase requirements, & blackout dates. Itinerary changes/cancellations are subject to Pleasant Holidays-imposed fees from $25 (for Canada or contiguous U.S. travel) or from $50 (for all other travel) per person, in addition to any applicable airline or other supplier-imposed change/cancellation penalties, plus applicable fare differentials (certain changes involve pre-notification deadlines). Airline fees & policies may vary; contact Pleasant Holidays for information. For baggage fees & other details, see www.iflybags.com. Rates involving roundtrip air transportation from other gateways may differ. Rates, terms, conditions, availability, itinerary, government taxes, surcharges, deposit, payment & cancellation terms & policies are subject to change without notice. Cruise rates capacity controlled. Advance reservations through AAA Travel required to obtain Member Benefits & savings which may vary based on departure date. Not responsible for errors or omissions. Pleasant Holidays acts only as an agent for cruise & tour providers listed. CST# 1007939-10. Copyright©2019 Pleasant Holidays, LLC. All Rights Reserved.


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