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. Browse our selection of Maui hotels and resorts and book a your vacation package today!
 

Exclusive 5-day two-category car rental upgrade
From midsize to convertible, Jeep, luxury or SUV

  • Minimum 5-night vacation packages
  • Book by 7/7/19 for travel through 12/14/19
All Deals Include: Round-trip flights, 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.

    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.
    • Hotel Room
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $930+

    Oakland, California (OAK) departures, valid for travel 08/26/19 - 08/31/19
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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 amid tropical gardens and features traditional Hawaiian touches.

    • Garden View
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $1028+

    Oakland, California (OAK) departures, valid for travel 08/26/19 - 08/31/19
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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.

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

    • Resort View
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • $20 Dining Credit per room per day

    5 nights with flight from $1090+

    Oakland, California (OAK) departures, valid for travel 08/26/19 - 08/31/19
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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
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $1122+

    Oakland, California (OAK) departures, valid for travel 08/26/19 - 08/31/19
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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.

    • Garden View Double
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • Reduced Rates

    5 nights with flight from $1470+

    Oakland, California (OAK) departures, valid for travel 08/26/19 - 08/31/19
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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
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $1540+

    Oakland, California (OAK) departures, valid for travel 08/26/19 - 08/31/19
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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
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • Daily $15 per person food & beverage credit towards breakfast at Cafe Kula or Grand Dining Room for ages 18 & older
    • 15% off spa services

    5 nights with flight and car from $1734+

    Los Angeles, California (LAX) departures, valid for travel 08/26/19
    See Details
Hawaii - Two-Category Car Rental Upgrade Offer: Valid on new bookings made 6/3 - 7/7/19 for travel 6/3 - 12/14/19. Roundtrip airfare and minimum 5 nights' hotel accommodation at participating hotel required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV for five days.
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.]