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 Travel & Testing Guidelines

In order to avoid a mandatory 14-day quarantine, travelers to Oahu, Maui and Island of Hawaii must take a COVID-19 test within 72 hours of the final leg of their flight to Hawaii and provide proof of a negative test result prior to boarding. Travelers must complete the State of Hawaii's Safe Travels online travel and health questionnaire and upload proof or a negative COVID-19 test result within 24 hours of flight departure to Hawaii. The test must be an FDA-approved NAAT COVID-19 test taken at an approved testing facility. Children ages 4 years and under are not required to provide a pre-travel test when traveling with parents. Effective December 2, all incoming trans-pacific and inter-county travelers to Kauai will face a mandatory 14-day quarantine.

For travel between the other Hawaiian Islands, another COVID-19 test may be required within 72-hours of arrival to bypass quarantine on Maui, Hawaii Island and Molokai. Inter-island passengers arriving on Oahu are not required to quarantine.  More information on each island's testing requirements is available here. Testing requirements are subject to change. Gov. David Ige has extended the statewide mask mandate, which requires all persons in the State to wear a face covering over their nose and mouth when in public.

Hawaii's Best Deals for 2021
Reduced room rates, spa discounts, dining credits and more

  • Book by 1/10/21 for travel through 6/30/21
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • 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.

    Book Now
  • Hyatt Regency Maui Resort & Spa
    Hyatt Regency Maui Resort & 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.

    Occupying 40 oceanfront acres of famed Ka'anapali Beach, the newly renovated Hyatt Regency Maui Resort and Spa offers unlimited activities and amenities in a setting of tropical paradise.

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  • 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.

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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.

    Located oceanfront on Kaanapali Beach, this oceanfront full-service condominium resort combines the comfort and convenience of spacious suites with full kitchens and hotel-caliber services.

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  • Honua Kai Resort & Spa
    Honua Kai Resort & Spa
    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.

    Situated on Kaanapali North Beach, this resort provides unparalleled service and all the amenities of a luxury resort with expansive one, two, and three bedroom suites.

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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.

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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.

    Relax beachfront or hang out poolside while you watch vibrant sunsets on this spectacular stretch of famed Ka’anapali Beach.

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  • 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 offers spacious rooms, 9 pools, 3-story tube slide, spa, fine dining with championship golf nearby.

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  • Andaz Maui at Wailea Resort - a concept by Hyatt
    Andaz Maui at Wailea Resort - a concept by Hyatt
    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 chic and vibrant resort features luxurious accommodations on a prime location on Mokapu Beach.

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  • Residence Inn Maui Wailea
    Residence Inn Maui Wailea
    Wailea, Maui 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 serene all-suite hotel in beautiful Wailea offers expansive accommodations and a host of amenities.

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  • The Kapalua Villas Maui
    The Kapalua Villas Maui
    Kapalua, Maui 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.

    Experience casual elegance, privacy and comfort in this tropical paradise. Expansive villa accommodations offer a wealth of amenities.

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  • Napili Shores by Outrigger
    Napili Shores by Outrigger
    Napili, Maui 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 condo resort is set in a private oceanfront setting amid expansive grounds, and offers well equipped accommodations.

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  • Aina Nalu Lahaina by Outrigger
    Aina Nalu Lahaina by Outrigger
    Lahaina, Maui 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.

    Just steps from Front Street in the heart of Lahaina town, this hotel is a sanctuary of contemporary serenity.

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  • Maui at the Eldorado by Outrigger
    Maui at the Eldorado by Outrigger
    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 neighborly and informal condominium resort provides a restful sanctuary. Comfortable accommodations offer garden or ocean views.

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  • Palms at Wailea Maui by Outrigger
    Palms at Wailea Maui by Outrigger
    Wailea, Maui 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 hotel is a refreshing oasis on a scenic bluff within luxurious Wailea, offering spacious accommodations and warm hospitality.

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  • Royal Kahana Maui by Outrigger
    Kahana, 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 oceanfront high-rise hotel offers a relaxed vibe and spacious accommodations.

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  • Courtyard by Marriott Maui Kahului Airport
    Courtyard by Marriott Maui Kahului Airport
    Maui, Kahului, HI 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.

    Conveniently located to Kahului Airport, this comfortable hotel features contemporary design and exclusive amenities.

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Hawaii's Best Deals for 2021 Travel: Valid on new bookings made 11/2/20 - 1/10/21 for select travel through 6/30/21. Minimum 3-night hotel accommodations at participating property and roundtrip 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.]