Maui Luxury Escape w/Flights & Car

For under $1000 per person, get a luxury Hawaii vacation that includes flight and rental car.

The Deal

TOP 20 – Sells out quickly!

The period after Christmas is one of the best times to get a deal on a Hawaii vacation. Escape the winter chill with this 5-star package that offers big savings — the hotel alone costs over $700 per night in the winter.

For $939 per person, this vacation includes:

  • Nonstop roundtrip flights to Maui
  • 3 nights at the luxe Grand Wailea, a Waldorf Astoria Resort (additional nights can be added)
  • Daily breakfast
  • 15% off spa treatments
  • Midsize car rental for 3 days

Depart: At the time of publication, we found the $939 price available for 3-night stays departing Jan. 9-16, 20-31; Feb. 1-9, 11 from San Francisco.

Other departure cities, like Los Angeles, Chicago, Boston and New York City, are also discounted.

Note: Pricing is per person, based on two travelers sharing a room. Solo traveler pricing is available upon request. Air and hotel taxes are included.

* Rates are based on roundtrip air travel as listed above, for select travel 1/4 – 2/21/19, and are per person, based on double occupancy. * 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. Subject to availability. Daily breakfast 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.]

When You Can Go

Jan. 9-16, 20-31; Feb. 1-9, 11


Up to $750 off DIY pricing

How to Book

In your search results, you may get an error message in a yellow box that says “There was a problem with your request” if you change your travel dates. Please ignore and proceed as pricing and dates will be correct.

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