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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.

Endless Summer in Hawaii - $100 OFF per booking

Book by 11/02/25 for select travel through 06/30/26

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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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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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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Aston Mahana at Kaanapali

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 beachfront condominium resort is the ideal tropical retreat with custom furnished oceanfront suites with full kitchens, floor-to-ceiling windows and private lanais.

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Aston at Papakea Resort

Kaanapali 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 picturesque oceanfront condominium resort is nestled amid 13 acres of lush tropical landscaping and expansive lawns.

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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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Hawaii $100 OFF per booking Offer: Valid on new bookings made 08/25/2025 – 11/02/2025 for select travel 08/25/2025 – 06/30/2026 unless otherwise stated. Minimum 5-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. 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.]