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Outrigger Resorts & Hotels, Hawaii

Enjoy great savings and exclusive discounts when you book an Outrigger Hawaii vacation package with Pleasant Holidays.

Voyager 47 Club Lounge

When you book our Club Room or Suites, you gain access to our premier club lounge, Voyager 47, luxuriously furnished with spectacular views and providing premium refreshments and elevated amenities, allowing guests to discover all that our destinations have to offer.

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OUTRIGGER Reef Waikiki Beach Resort

OUTRIGGER Waikiki Beach Resort

OUTRIGGER Kona Resort & Spa

Oahu

OUTRIGGER Waikiki Beach Resort

Waikiki, Oahu 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.

Escape to sun, sand & surf on legendary Waikiki Beach. From the beach boys to Duke's Waikiki, experience beach life with live music and entertainment, vibrant cultural events, and accommodations overlooking iconic Waikiki Beach and Diamond Head.

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OUTRIGGER Reef Waikiki Beach Resort

Waikiki, Oahu 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 distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

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Embassy Suites by Hilton Waikiki Beach Walk

Waikiki, Oahu 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 all-suite Waikiki resort boasts free daily breakfast, evening poolside reception, and a prime location steps from Waikiki Beach and top shopping, dining, and cultural experiences at Waikiki Beach Walk®.

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OUTRIGGER Waikiki Beachcomber Hotel

Waikiki, Oahu 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.

Steps from the beach, Hawaii's only handcrafted Hotel in the Heart of Waikiki. Curated by local artists and influencers, inspiring beach, culture, and art. Infused stylish hotel rooms and suites with unique personality and culture of the island.

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OUTRIGGER Waikiki Paradise Hotel

Waikiki, Oahu 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.

Discover exceptional value at this family-friendly hotel offering one- and two-bedroom suites with kitchenettes in the heart of Waikiki, just five minutes from the beach.

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Regency on Beachwalk Waikiki by OUTRIGGER

Waikiki, Oahu 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 in the heart of Waikiki, just a short walk from the beach, and adjacent to Waikiki Beach Walk.

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Maui

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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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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The Kapalua Villas Maui

Kapalua, 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.

Experience casual elegance, privacy and comfort in this tropical paradise. Expansive villa accommodations offer a wealth of amenities.

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Napili Shores by OUTRIGGER

Napili, Maui 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 condo resort is set in a private oceanfront setting amid expansive grounds and offers well-equipped accommodations.

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Palms at Wailea Maui

Wailea, Maui 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 condo is a refreshing oasis on a scenic bluff within luxurious Wailea, offering spacious accommodations and warm hospitality.

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Royal Kahana Maui by OUTRIGGER

Kahana, 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.

This oceanfront high-rise hotel offers a relaxed vibe and spacious accommodations.

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Kauai

Waipouli Beach Resort & Spa Kauai by OUTRIGGER

Kapaa, Kauai 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 distinctive resort offers comfortably appointed condos and a heated river pool spanning over two acres.

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Kiahuna Plantation Resort Kauai by OUTRIGGER

Poipu, Kauai 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 beautifully appointed resort occupies a lovely beachfront in sunny Poipu and is reminiscent of Hawaii's gracious plantation era.

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OUTRIGGER Kaua'i Beach Resort & Spa

Kauai, Lihue, HI 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.

Escape to paradise directly on Nukolii Beach on the Garden Isle's east shore. Experience Hawaiian hospitality across 25 lush tropical acres, centrally located between Kauai's north and south shores.

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Hawaii

Fairway Villas Waikoloa by OUTRIGGER

Waikoloa 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 distinctive oasis is perfectly situated in the exclusive Waikoloa Resort area, just a short stroll from the golden sands at Historic Anaehoomalu Bay.

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OUTRIGGER Kona Resort and Spa

Kona 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.

A legendary Kona resort reborn at Keauhou Bay. Take in spectacular views from iconic Keauhou cliffs. Relax in welcoming rooms and social spaces. Sip at oceanfront pools. Marvel at Feast & Fire Luau. Immerse with daily cultural activities.

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Royal Sea Cliff Kona by OUTRIGGER

Kona 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.

Rising above the sea on a dramatic bluff, this condominium resort affords uninterrupted ocean views and peaceful surroundings.

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