Maui Beach, Lanai in background

Maui Vacation Packages

 
Maui consistently lands atop travel-magazine reader polls as one of the world's best, most romantic islands. Why? How about a wealth of glorious beaches, luxe resorts, gourmet cuisine, fantastic luaus, and world-class windsurfing, whale watching, snorkeling, diving and hiking? Maui is known as the 'Valley Island' because of its two large extinct volcanoes divided by a tropical central valley. It's the second-largest of the Hawaiian islands and the most developed of the Neighbor Islands. Its windsurfing and surf spots are some of the best in the world.
 

Hawaii's Best Deals

  • Up to 60% OFF room rates
  • Buy One Activity, Get One for 60% OFF
  • Book by 1/13/19 for travel through 12/31/19
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
  • Lahaina Shores Beach Resort
    Lahaina Shores Beach Resort
    Lahaina, Maui Our 2.5-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Set on the ocean's edge in Lahaina Town along historic Front Street, this condo resort features spacious accommodations and a wealth of activities at your doorstep.

    • Studio Mountain View Premier
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)

    3 nights with flight from $643+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
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  • Ka'anapali Beach Hotel
    Ka'anapali Beach Hotel
    Kaanapali Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    This beautiful hotel is set amongst tropical gardens and features traditional Hawaiian touches.

    • Pool View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • No resort fee
    • Complimentary hula shows, daily interactive Hawaiian cultural activities, year round children's program, daily arts and crafts fair and departure Kukui lei ceremony
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $804+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Ka'anapali Beach Hotel
    Ka'anapali Beach Hotel
    Kaanapali Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    This beautiful hotel is set amongst tropical gardens and features traditional Hawaiian touches.

    • Pool View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • No resort fee
    • Complimentary hula shows, daily interactive Hawaiian cultural activities, year round children's program, daily arts and crafts fair and departure Kukui lei ceremony
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $839+

    Los Angeles, California (LAX) departures, valid for travel 03/18/19
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  • Aston Kaanapali Shores
    Aston Kaanapali Shores
    Kaanapali Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This deluxe condominium resort combines the comfort and convenience of a condominium with hotel-caliber services.
    • Hotel
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $891+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Sheraton Maui Resort & Spa
    Sheraton Maui Resort & Spa
    Kaanapali Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    This oceanfront resort in the heart of Kaanapali, Maui features recently renovated rooms and suites ideal for honeymoons.

    • Resort View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $955+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Grand Wailea, A Waldorf Astoria Resort
    Grand Wailea, A Waldorf Astoria Resort
    Wailea, Maui Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Voted one of the Best Resort in Hawaii in the 2018 Condé Nast Readers' Choice Awards, this luxury Hilton beachfront resort offers spacious rooms, 9 pools, 3-story tube slide, spa, fine dining with championship golf nearby.
    • Run of House
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Daily continental breakfast in Cafe Kula or Grand Dining Room for ages 18 & older
    • 15% off spa services
    • Complimentary lei greeting and welcome drink
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1045+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • The Westin Maui Resort & Spa, Kaanapali
    The Westin Maui Resort & Spa, Kaanapali
    Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Commanding a spectacular stretch of Kaanapali Beach, this magnificent resort offers a family-friendly getaway.
    • Mountain View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1053+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • The Westin Nanea Ocean Villas
    The Westin Nanea Ocean Villas
    Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Located on North Ka’anapali Beach, this new resort features spacious one, two and three-bedroom villas with luxurious amenities accommodating up to 8 adults.
    • Resort View One Bedroom Villa
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • 3 breakfast buffet vouchers per stay (valid for stays January 3 - December 21, 2019)
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1202+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • The Westin Kaanapali Ocean Resort Villas
    The Westin Kaanapali Ocean Resort Villas
    Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Set on 26 pristine oceanfront acres, this resort offers a unique blend of resort and villa-style living.
    • Studio Island View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1271+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
  • Wailea Beach Resort - Marriott, Maui
    Wailea Beach Resort - Marriott, Maui
    Wailea, Maui Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This magnificent resort on 22 oceanfront acres on Maui's sunny side has been transformed to embrace the beauty of its natural surroundings.

    • Garden View
    • Hawaii Vacation Sale - Up to 60% OFF on room rates in honor of Pleasant Holidays 60th anniversary
    • Includes FREE transfers for all Waikiki hotels and Buy One Get One 60% OFF on activities (excluding activities that include air/helicopter)
    • Connecting rooms available upon request
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1429+

    San Francisco, California (SFO) departures, valid for travel 03/18/19
    See Details
Hawaii - Best Deals offers: Valid on new bookings made 10/29/18 - 1/13/19 for travel 10/29/18 - 12/31/19. Accommodation at participating resort and roundtrip transpacific airfare required. Room rate savings and minimum night stay vary by participating resort. Travelers will receive a voucher valid to buy one activity and get one activity of equal or lesser value for 60% off the retail value redeemable at any Pleasant Activities Center or the Pleasant Holidays Island Orientation in Hawaii or via the Hawaii Call Center by calling 1-888-229-7770. Fees and surcharges are excluded and must be paid for both tours. Limit of one discounted activity per booking. Offer does not apply to activities involving flights (plane or helicopter). Complimentary roundtrip shared airport transfers valid to/from HNL and any Waikiki hotel or resort in Pleasant Holidays' Oahu portfolio; offer does not apply to any hotels or resorts outside of Waikiki. Activity voucher and airport transfers have no cash value, are non-transferrable, are not combinable with any other offers, apply only to the vacation on which they were booked and expire at the end of booking's travel dates. Offer subject to availability and may be changed or cancelled at any time. Certain restrictions and blackout dates may apply.
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.]