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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.

Hawaii Summer & Fall Savings

Room upgrades, resort credits, FREE breakfast offers, and more

Book by 08/24/25 for select travel through 12/31/25

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.

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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.

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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.

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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.

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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.

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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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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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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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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.

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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.

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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.

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Hawaii Summer & Fall Savings: Valid on new bookings made 06/30/2025 – 08/24/2025 for select travel through 12/31/2025 unless otherwise indicated. Valid on new bookings for select travel through 12/31/2025 unless otherwise indicated. All offers require inclusion of roundtrip transpacific air and accommodations in select room categories noted above. Certain restrictions and blackout dates may apply. All offers and programs apply to a limited number of rooms, and are subject to availability, change or cancellation without notice.

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]