Maui Beach, Lanai in background

Maui Vacation Packages

from $699
 
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.
 

EXCLUSIVE $100 OFF per booking

  • On minimum 3-night vacation packages
  • Book by 10/28/18 for travel through 6/30/19
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
  • 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.
    • Studio with Kitchen
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE

    3 nights with flight from $699+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
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  • Castle Kamaole Sands
    Castle Kamaole Sands
    Kihei, 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.

    This resort is set amid tropical gardens with waterfalls and ponds, just a short stroll to the charming town of Kihei.
    • One Bedroom Partial Oceanview
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $707+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
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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.

    • Garden View
    • Exclusive $100 Off per booking
    • 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 $727+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
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  • Royal Lahaina Resort
    Royal Lahaina Resort
    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 unique resort set along Kaanapali Beach offers natural beauty, traditional Hawaiian ambiance and attentive service.
    • Run of House
    • Exclusive $100 Off per booking
    • Reduced rates
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $765+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
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  • 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.

    Set at the foot of Black Rock, affording spectacular views, this hotel honors its legendary location and Hawaiian heritage.

    • Resort View
    • Exclusive $100 Off per booking
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $779+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
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  • 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
    • Exclusive $100 Off per booking
    • Daily buffet breakfast for two
    • 15% spa discount
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $822+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
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  • Hyatt Regency Maui Resort and Spa
    Hyatt Regency Maui Resort and Spa
    Kaanapali 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.

    Located on 40 oceanfront acres on Ka`anapali Beach, spectacular resort features a half-acre pool and endless entertainment options.
    • One Queen and One Double Bed
    • Exclusive $100 Off per booking
    • Connecting rooms available upon request
    • Kids 18 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $867+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
    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.

    This luxury Hilton beachfront resort is set on 40 acres bordering Maui's Wailea Beach with spacious rooms, 9 pools, 3-story tube slide, spa, fine dining with championship golf nearby.
    • Run of House
    • Exclusive $100 Off per booking
    • 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 $894+

    San Francisco, California (SFO) departures, valid for travel 01/28/19
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  • Fairmont Kea Lani, Maui
    Fairmont Kea Lani, Maui
    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.

    Maui's only all-suite and villa luxury oceanfront resort features elegant accommodations with sophisticated amenities in the upscale Wailea resort area.

    • Fairmont Garden View Double
    • Exclusive $100 Off per booking
    • Reduced rates
    • Complimentary lei greeting and welcome drink
    • Connecting rooms available upon request
    • Kids 18 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1053+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
    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
    • Exclusive $100 Off per booking
    • Reduced rates
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1144+

    Los Angeles, California (LAX) departures, valid for travel 12/03/18
    See Details
Hawaii - $100 OFF per booking offer: Valid on new bookings made 8/27 - 10/28/18 for travel 8/27/18 - 6/30/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip transpacific airfare required. Discount is per booking, taken at time of booking and reflected in rates shown.
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.]