2020 Hawaii Vacations

The Guaranteed Lowest Prices on All Four Islands

  • Exclusive reduced room rates
  • Spa discounts
  • Kids stay FREE offers
  • And more
Kauai Marriott Resort

Kauai Marriott Resort

Majestic waterfalls, blue lagoons, and lush tropical surroundings distinguish this deluxe Hawaiian resort set on beautiful Kalapaki Bay.

3 nights with air from $745

Sheraton Kona Resort & Spa at Keauhou Bay, Island of Hawaii

Sheraton Kona Resort & Spa at Keauhou Bay, Island of Hawaii

Dramatic views, a romantic bayside chapel and multi-level pools and waterslide fill this 22-acre tropical playground. Indulge in luxurious treatments at Ho´ola Spa, irresistible island fare and daily Cultural Performances at this Kona Coast resort.

3 nights with air from $615

Moana Surfrider, A Westin Resort & Spa, Waikiki

Moana Surfrider, A Westin Resort & Spa, Waikiki

Renowned as “The First Lady of Waikiki,” this legendary resort built in 1901 blends Victorian elegance and modern amenities into a truly memorable experience. Replenish at the oceanfront Moana Lani Spa and dine on gourmet cuisine at The Beachhouse at the Moana.

3 nights with air from $815

The Royal Hawaiian, A Luxury Collection Resort, Waikiki

The Royal Hawaiian, A Luxury Collection Resort, Waikiki

Built in 1927, the “Pink Palace of the Pacific,” offers discerning travelers a luxury experience. Guests can enjoy the historic ambiance or the new Mailani Tower with its exclusive lounge, a private haven within the resort.

3 nights with air from $915

The Westin Maui Resort & Spa, Kaanapali Beach

The Westin Maui Resort & Spa, Ka’anapali Beach

Set on the widest stretch of Ka’anapali Beach, this oceanfront resort pampers guests with generous amenities and an award-winning spa. Take the plunge at the expansive aquatic playground with its thrilling waterslide and private adults-only pool, and enjoy the on-site luau.

3 nights with air from $839

Hawaii - Hot Deals EXCLUSIVE $100 OFF per booking offer: Valid on new bookings made 8/26 - 10/27/19 for travel 8/26/19 - 6/30/20. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required. Savings is $100 per booking, taken at time of booking and reflected in rates shown.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]