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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.

When visiting Maui, remember to Travel Pono—to travel responsibly and thoughtfully—and show your Aloha for Maui’s cultures and communities. Respect areas that are healing and take time to appreciate the magic of the island. For those interested in helping to support the Island of Maui in its recovery efforts, while giving back to local communities on the island, visit Hands On Maui to find opportunities for volunteer services.
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Hawaii - The Best Deals
Room upgrades, resort credit, FREE breakfast offers and more

  • Book by 01/04/26 for select travel through 01/07/27

  • 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.
    This upscale resort set along a spectacular stretch of Kaanapali Beach features elegant guest rooms and an expansive aquatic playground with waterfalls, waterslides and a serene adults-only pool.
    Book Now
    This upscale resort set along a spectacular stretch of Kaanapali Beach features elegant guest rooms and an expansive aquatic playground with waterfalls, waterslides and a serene adults-only pool.
    Book Now
  • OUTRIGGER Honua Kai Resort & Spa

    OUTRIGGER 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.
    Book Now
    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.
    Book Now
  • 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.
    Connect to Maui like never before at this resort, Hawaii’s only all-suite and villa luxury oceanfront property.
    Book Now
    Connect to Maui like never before at this resort, Hawaii’s only all-suite and villa luxury oceanfront property.
    Book Now
  • 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.
    On a beach surrounded by a tropical landscape, this resort offers an oceanfront paradise featuring luxurious accommodations, award-winning cuisine, locally inspired spa treatments and extraordinary pools.
    Book Now
    On a beach surrounded by a tropical landscape, this resort offers an oceanfront paradise featuring luxurious accommodations, award-winning cuisine, locally inspired spa treatments and extraordinary pools.
    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.
    Located on 40 acres on Ka'anapali Beach, this oceanfront oasis offers unlimited activities and amenities featuring interiors with authentic Hawaiian finishes.
    Book Now
    Located on 40 acres on Ka'anapali Beach, this oceanfront oasis offers unlimited activities and amenities featuring interiors with authentic Hawaiian finishes.
    Book Now
  • 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.
    Book Now
    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.
    Book Now
  • 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.
    Experience oceanfront luxury at Sheraton Maui Resort & Spa on Kaʻanapali Beach. Enjoy lagoon-style pools, cultural activities, snorkeling, and stunning views of Lanaʻi and Molokaʻi. Perfect for romance, family fun, and unforgettable sunsets.
    Book Now
    Experience oceanfront luxury at Sheraton Maui Resort & Spa on Kaʻanapali Beach. Enjoy lagoon-style pools, cultural activities, snorkeling, and stunning views of Lanaʻi and Molokaʻi. Perfect for romance, family fun, and unforgettable sunsets.
    Book Now
  • 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.
    Book Now
    This chic and vibrant resort features luxurious accommodations on a prime location on Mokapu Beach.
    Book Now
  • 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.
    Book Now
    This magnificent resort on 22 oceanfront acres on Maui's sunny side has been transformed to embrace the beauty of its natural surroundings.
    Book Now
  • OUTRIGGER Ka'anapali Beach Resort

    OUTRIGGER Ka'anapali Beach 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 beachfront paradise embodies Hawaii's soul and is known as "Maui’s most Hawaiian resort." Come be here and turn your dreams into lifelong memories with authentic island experiences.
    Book Now
    This beachfront paradise embodies Hawaii's soul and is known as "Maui’s most Hawaiian resort." Come be here and turn your dreams into lifelong memories with authentic island experiences.
    Book Now
  • Royal Lahaina Resort & Bungalows

    Royal Lahaina Resort & Bungalows

    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.
    Book Now
    This unique resort set along Kaanapali Beach offers natural beauty, traditional Hawaiian ambiance and attentive service.
    Book Now
  • The Ritz-Carlton Maui, Kapalua

    The Ritz-Carlton Maui, 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.
    Unwind in spacious rooms and suites thoughtfully tailored with luxurious amenities at this iconic, newly reimagined beachfront resort surrounded by 22,000 acres of lush, tropical landscapes on Maui's pristine northwest shore.
    Book Now
    Unwind in spacious rooms and suites thoughtfully tailored with luxurious amenities at this iconic, newly reimagined beachfront resort surrounded by 22,000 acres of lush, tropical landscapes on Maui's pristine northwest shore.
    Book Now
1-800-742-9244
  • Hawaii - The Best Deals Offer: Valid on new bookings made 11/03/2025 – 01/04/2026 for select travel 11/03/2025 – 01/03/2027 unless otherwise stated. Offers vary by hotel and travel dates, and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Certain restrictions and blackout dates may apply. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
  • Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]
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