Grand Wailea Spring Sale

Exclusive FREE 3-day convertible, SUV, Jeep or luxury car rental + daily breakfast credit and 15% off spa treatments

on minimum 3-night stays. Book by 2/24/19 for travel 1/31 - 12/14/19 with no blackout dates.

Book Online or Call 877-487-2835

Grand Wailea room

FREE 3-day UPGRADED rental car at the Grand Wailea, A Waldorf Astoria Resort

These incredible prices include roundtrip airfare, 3 luxurious nights at the Grand Wailea, a FREE lei greeting, a $15 per person daily breakfast credit, 15% off spa treatments, and FREE 3-day upgraded car rental.

Need more time in paradise? Our vacations are customizable for any length of stay, conveniently departing from most major US gateways.

Travel anytime before December 14, 2019, but we're seeing best rates for Spring travel. Example rates per person for 2 travelers departing 2/18, returning 2/21:
From San Francisco (SFO) – 3 nights with air from $880
From Los Angeles (LAX) – 3 nights with air from $886
From Las Vegas (LAS) – 3 nights with air from $965     
From San Diego (SAN) – 3 nights with air from $968     
From Boston (BOS) – 3 nights with air from $1,120
From New York (JFK) – 3 nights with air from $1,237

FREE 3-day UPGRADED rental car when booking

• Moana Surfrider, a Westin Resort & Spa, Waikiki
• The Royal Hawaiian, A Luxury Collection Resort, Waikiki
• Kauai Marriott Resort
• Sheraton Kona Resort & Spa at Keauhou Bay

Get our lowest rates, available online only, for travel to

• Oahu
• Maui
• Kauai
• Island of Hawaii
Rates are based on roundtrip air travel as listed above, for select travel 1/31 - 12/14/19, and are per person, based on double occupancy.

FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 1/30 - 2/24/19 for travel 1/31 - 12/14/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required. Bookings receive FREE a 3-day convertible, SUV, Jeep or luxury car rental; additional car rental days may be added at additional rate. Value of 3-day car rental may not be redeemed for cash or discounted off the vacation package price. Age restrictions may apply for car rental.

* 2019 Exclusive Rates and Extras at the Grand Wailea: Valid on new bookings for travel 1/4/19 - 1/3/20 in select room categories. Savings is based on hotel room rate for a five-night stay compared to highest available rate for comparable Terrace room category. Subject to availability. $15 breakfast credit per adult is available in Café Kula or the Grand Dining Room. Roundtrip transpacific airfare required.
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.]