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.
 

FREE 3-day midsize Hertz car rental

Value of midsize car may be applied to car upgrade
Exclusive check-in at Hawaii airports

Minimum 3-night vacation packages
Book by 2/24/19 for travel through 12/14/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
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  • 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
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Reduced rates

    3 nights with flight from $550+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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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/Courtyard
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Reduced rates
    • Complimentary one-category room upgrade

    3 nights with flight from $628+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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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.

    Located oceanfront on Kaanapali Beach, this deluxe oceanfront full-service condominium resort combines the comfort and convenience of spacious suites with full kitchens and hotel-caliber services.
    • Studio with Kitchen
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Reduced rates

    3 nights with flight from $671+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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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.
    • Tower Standard
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $697+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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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 Double Double Non-smoking Suite
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Reduced rates

    3 nights with flight from $844+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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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.

    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
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental
    • Daily $15 per person food & beverage credit towards breakfast at Cafe Kula or Grand Dining Room for ages 18 & older
    • 15% off spa services

    3 nights with flight from $915+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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  • Wailea Beach Resort
    Wailea Beach Resort
    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
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $977+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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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.
    • One King Mauka View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $1074+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
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  • The Ritz-Carlton Maui at Kapalua
    The Ritz-Carlton Maui at Kapalua
    Kapalua, 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 magnificent resort features two championship golf courses and a wealth of exclusive amenities.

    • Terrace
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $1092+

    Los Angeles, California (LAX) departures, valid for travel 05/13/19 - 05/16/19
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  • Kaanapali Alii
    Kaanapali Alii
    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.

    These luxury beachfront condominiums have become the preferred vacation address for the active traveler.
    • One Bedroom Garden View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $1162+

    San Diego, California (SAN) departures, valid for travel 05/20/19 - 05/23/19
    See Details
Hawaii - FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 1/7 - 2/24/19 for travel 1/7 - 12/14/19. Minimum 3 nights' hotel accommodation at participating resort and roundtrip airfare required. Bookings receive FREE a 3-day midsize car rental; additional car rental days may be added at additional rate. Value of 3-day midsize car rental may be applied to upgraded car classes, but may not be redeemed for cash or discounted off the vacation package price. Age restrictions may apply for car rental.
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.]