« Back to Vacations

Escape to the tropical Sheraton Maui Resort & Spa with Pleasant Holidays
from $1,439 pp

  • Duration: 6 Days
  • Destinations: Hawaii

Discover Hawaii's natural beauty when you stay at the Sheraton Maui Resort & Spa. Anchored at the famed Black Rock overlooking Kaanapali Beach, make lasting memories as you snorkel with tropical fish and honu (green sea turtles), learn ukulele with family or experience the iconic Torch Lighting and Cliff Dive ceremony at sunset at this spectacular beachfront resort.Take a dip in the oceanfront lagoon pool. Explore several large swimming areas on a floating beanbag chair, interconnected by lava-rock waterways, along with a lazy river and a waterslide. Make your stay your own with the help of Pleasant Holidays and AAA Travel.

Founded over 60 years ago, Pleasant Holidays is one of the largest travel companies in the United States offering customized vacation packages all over the world! Plan everything with a AAA Travel advisor: your flight, accommodation preference — all-inclusive or luxury, renting a car, sightseeing activities, and even travel protection coverage to preserve what you have to look forward to.

Special Offers and Member Benefits:

  • Up to $100 per booking savings*
    • $50 activity credit
    • $50 savings off next vacation
  • Kids 17 & younger stay FREE!
  • 24/7 Member Care
  • Best Price Guarantee

Travel with Peace of Mind

  • $99 per person - Cancel-for-any-reason coverage **
  • Travel suppliers with enhanced health, safety and sanitation protocols
  • Participation in the United States Tour Operators Association $1 Million Travelers Assistance Program

Where You Will Stay:

Located on 23 lush oceanfront acres at legendary Pu’u Keka’a on Ka’anapali Beach, the newly renovated 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. The ideal choice for honeymoons.

What You Will See:

Relax at the resort's spa, swim in the lagoon pool, or explore nearby Lahaina. Immerse yourself in Hawaiian culture on a hiking tour with a local guide or at the nightly Cliff Dive Ceremony with live entertainment. Learn to paddleboard, scuba or snorkel.

Resort Amenities Include: 

  • 142-Yard Lagoon-Style Pool
  • The Spa at Black Rock
  • Hawaiian cultural activities
  • Tennis
  • Koi Pond and more!

Where You May Eat:

ROCKsalt: Experience exotic spices, ingredients and flavors combined with local products from Hawaii farms as you indulge in globally-inspired plates that are playful, flavorful and alluring. The menu includes small and large plates, all of which are meant to be shared. 

Mai Tai Bar: Located steps from Kaanapali Beach, Mai Tai Bar is your ideal setting for sipping on drinks and savoring tasty poolside snacks.

Dinner Under the Stars: This program features enticing menus, private butler and your personal selection of dining location among 23 acres of foliage and ocean views.

 
Call to Book 1-800-222-7448
Additional Information

Rate is per person, land only, based on double occupancy, for a five-night stay beginning on 12/13/2021 in a Resort View room. Age restrictions may apply.

*$50 per booking savings. Does not apply to air/car only packages. In addition, members will receive a "Bounce Back Offer" to be booked within 12 months of their original booking with no travel expiration date. $50 per booking savings off of the member's next vacation to non-Mainland USA / international travel that includes three nights accommodations. Member Benefit doubles on packages 5 nights or more. Bounce Back does not apply to Air by Pleasant. United States bounce back/FTC 3-night minimum. Groups: Negotiated on a case-by-case basis. Call for more details.

**$99 Per Person Cancel-For-Any-Reason, Travel Protection Coverage valid on new bookings through 03/31/21. Cash back and future travel credit options available, prices may vary. Call a AAA Travel advisor for more details.

General Terms and Conditions: Unless otherwise indicated: rates quoted are accurate at time of publication, & are per person, based on double occupancy. Airfare, taxes, surcharges, gratuities, transfers & excursions are additional. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel at check-out; such fee amounts will be advised at the time of booking. Rates, terms, conditions, availability, itinerary, government taxes, surcharges, deposit, payment, cancellation terms/conditions & policies subject to change without notice at any time. Cruise rates capacity controlled. Other restrictions may apply, including, but not limited to baggage limitations & fees, standby policies & fees, non-refundable tickets & change fees with pre-flight notification deadlines, & blackout dates. Fees & policies vary among airlines. Contact airline directly for any details or questions. 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. Pleasant Holidays is registered with the State of Florida as a Seller Of Travel ST#37983. Copyright©2021 Pleasant Holidays, LLC. All Rights Reserved.

Departure Dates
Start: March 1, 2021
End: January 3, 2022
Price: $1,439 pp


Get an Estimate
Get an Estimate
Product Code: AAA-FIS20_090120_PH_CC

All pricing and offers for accommodations and other non-air travel are per person, based on double occupancy, capacity controlled and subject to availability and change without notice. Pricing does not include taxes, fees, fuel surcharges, gratuities, resort fees, or airfare unless otherwise noted and is valid on new bookings only. Prices, fees, and other restrictions are subject to supplier policies. All offers, including but not limited to, bonus amenities, upgrades, prices, and group benefits are based on select dates, resorts, room categories, and/or fare codes. Specialty pricing may require proper identification. Cancellation penalties, blackout dates, and other restrictions may apply. When traveling outside the United States a valid passport is required. It is the sole responsibility of the passenger to have the proper documentation and identification required by the United States and other governments at the time of travel. When passports are required, it must be valid for a minimum of six months past your date of return. AAA strongly recommends the purchase of AAA Travel Protection. Usage of a credit card for travel arrangements may provide additional protection, please consult your credit card policies. Under certain circumstances the package price may be subject to supplemental price increases imposed by the supplier. Price increases include, but are not limited to fuel surcharges, taxes or fluctuations in foreign exchange markets that may be imposed after the date of purchase. Air-inclusive prices do not include government imposed taxes and fees, including but not limited to a September 11th Security Fee, U.S. or international government imposed taxes and fees, Federal Excise Fees, among others. Some carriers charge additional fees for checked bags, fuel surcharge, meals, etc. Please check the carriers website for details. Air-inclusive pricing is based on select departure cities. Prices from other cities may vary. AAA Northeast acts solely as a sales agent for travel suppliers and is not responsible for the actions or inactions of such suppliers. We monitor all of the information presented on our website; however, we do not assume responsibility for any errors or omissions in the content of the offers displayed. Review full Travel Disclosure and Consent at time of booking.

Airfare, taxes, surcharges, gratuities, transfers, port charges and excursions are additional unless otherwise indicated. Fuel surcharges, government taxes, other surcharges, deposit, payment and cancellation terms/conditions are subject to change without notice. Baggage fees are not included in your trip cost, you should re-verify with the airline directly or on their website prior to your departure for current details on allowable luggage pieces, fees, size and weight limitations since they vary from airline to airline. See link to research baggage fees and information: http://www.iflybags.com. Rates quoted are per person, land only, based on adult double occupancy unless otherwise stated. Discounts, products, vendors, rates, terms, conditions, availability and itinerary are subject to change without notice. Cruise rates are capacity controlled. Certain restrictions may apply. AAA members must make advance reservations through AAA Travel to obtain Member Benefits and savings. Member Benefits may vary based on departure date. Be advised that any and all costs associated with air reservations made outside of these packages will not be refunded by AAA or the tour operator in the event of an unforeseen change and/or cancellation by you and/or the tour operator. Not responsible for errors or omissions. Rates are accurate at the time of printing and are subject to availability and change. AAA Northeast acts only as an agent for the various tour and/or cruise providers listed and is not responsible for the actions or inactions of such providers. AAA Vacations® Best Price Guarantee and 24/7 Member Care are applicable to AAA members only. If you book a qualifying AAA Vacations® cruise or tour package and find a valid better rate for the exact itinerary within 24 hours of your booking, AAA will match the lower rate and send you a $50 AAA Vacations® future travel credit certificate. Certain restrictions apply. Visit AAA.com/AAAVacations for full details.

AAA Travel Alert: During these uncertain times, many travel destinations have implemented COVID-19-related health and safety restrictions and entry requirements. Please check to see if local authorities, hotels, cruise lines, tour operators, attractions, and restaurants at your intended travel destination have issued health and safety-related alerts, entry requirements or other restrictions. These new travel restrictions may be imposed or amended with little warning. Failure to comply with applicable rules may result in denied entry or quarantine upon arrival. (Note: As things change, so do policies. We’ll do our best to stay on top of things, but always be sure to check with a provider directly.)