Grand Wailea 2019 Sale
Exclusive FREE 3-day intermediate car rental + Ocean View room + daily breakfast credit and 15% off spa treatments

  • on minimum 3-night stays

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 in an Ocean View or Run of House room, 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 20, 2019, but we're seeing best rates for travel in late August or October. Example rates per person for 2 travelers departing 8/26/19 or 10/28/19:

From San Francisco (SFO) – 3 nights with air from $895 pp
From Los Angeles (LAX) – 3 nights with air from $975 pp

Explore these other exclusive Pleasant Holidays Hawaii Deals

• The Royal Hawaiian, A Luxury Collection Resort, Waikiki
• Moana Surfrider, a Westin Resort & Spa, Waikiki
• Kauai Marriott Resort
• Sheraton Kona Resort & Spa at Keauhou Bay
Rates are based on roundtrip air travel as listed above, for select travel through 12/20/19, and are per person, based on double occupancy.

FREE 3-Day Hertz Car Rental offer: Valid on new bookings made through 7/31/19 for travel through 12/20/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required. Bookings receive FREE a 3-day intermediate 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.]