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You've been dreaming of a Hawaii vacation with those amazing beaches, palm trees swaying, hiking trails abound in the gorgeous mountain ranges, surrounded by an endless blue & green ocean just waiting for you to play in. Book your Dreamcation today and save 35%! Choose from Oahu, Maui, Kauai, Molokai, and the Big Island...

Oahu - The Gathering Place

Waikiki Shore

Condominium: Waikiki, Oahu

The only beachfront condo resort on Waikiki Beach, steps from Waikiki's best shopping, dining, and activities.

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Travel: 06/01/2020 - 01/31/21
Rates from $185 $121* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Waikiki Grand

Hotel: Waikiki, Oahu

Located steps from Waikiki Beach, this hotel features moderately-priced rooms with ocean or Diamond Head views.

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Travel: 06/01/2020 - 01/31/21
Rates from $109 $71* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Kauai - The Garden Isle

Kaha Lani Resort

Resort: Lihue, Kauai

Secluded oceanfront condominium resort minutes from Lihue and Kapaa with full kitchens and spectacular ocean views.

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Travel: 06/01/2020 - 01/31/21
Rates from $159 $102* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Kauai Kailani Resort

Condominium: Kapaa, Kauai

Recently-renovated 1- and 2-bedroom suites with full kitchens and free WiFi conveniently located in Kapaa town.

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Travel: 06/01/2020 - 01/31/21
Rates from $129 $84* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Extraordinary Poipu condo resort nestled on 35 beachfront acres with spacious suites and many resort amenities.

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Travel: 06/01/2020 - 01/31/21
Rates from $169 $110* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Makahuena at Poipu

Condominium: Poipu, Kauai

Unique oceanfront condo resort in Poipu with 2-, and 3-bedroom suites with full kitchens and washer/dryers.

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Travel: 06/01/2020 - 01/31/21
Rates from $239 $156* *Excluding Taxes & Fees
Book: Now - 05/31/2020

The ISO

Hotel: Kapaa, Kauai

Where Island, Sky and Ocean meet, this is The ISO. Features newly-renovated rooms with ocean views and an award-winning restaurant.

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Travel: 06/01/2020 - 01/31/21
Rates from $129 $84* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Poipu Shores

Condominium: Poipu, Kauai

Oceanfront condo on the spectacular Poipu Coast. Choose from 1-, 2- and 3-bedroom suites, all with full kitchens.

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Travel: 06/01/2020 - 01/31/21
Rates from $179 $117* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Hawaii - The Big Island

Halii Kai at Waikoloa Resort

Resort: Waikoloa, Hawaii

Luxurious villas on 29 oceanfront acres in Waikoloa Resort with cascading pool, restaurant, golf, and more.

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Travel: 06/01/2020 - 01/31/21
Rates from $199 $130* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Hilo Hawaiian

Hotel: Hilo, Hawaii

Located on Hilo's historic Banyan Drive, this full-service, oceanfront hotel offers recently-renovated guest rooms.

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Travel: 06/01/2020 - 01/31/21
Rates from $109 $71* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Kanaloa at Kona by Castle

Condominium: Kailua-Kona, Hawaii

Overlooking Keauhou Bay, Kanaloa at Kona offers spacious one and two-bedroom suites and fantastic resort amenities.

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Travel: 06/01/2020 - 01/31/21
Rates from $109 $71* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Kona Bali Kai Resort

Condo Resort: Kailua-Kona, Hawaii

This oceanfront Kona resort offers great value and comfortable studios, one and two bedroom suites.

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Travel: 06/01/2020 - 01/31/21
Rates from $115 $75* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Kona Reef Resort

Condo Resort: Kailua-Kona, Hawaii

Oceanfront condo resort steps from historic Kailua-Kona town and its charming shops, restaurants, and attractions.

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Travel: 06/01/2020 - 01/31/21
Rates from $149 $97* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Waimea Country Lodge

Hotel: Waimea, Hawaii

Rustic 21-room lodge in historic Waimea Town at the foothills of Mauna Kea, the highest mountain in the Pacific.

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Travel: 06/01/2020 - 01/31/21
Rates from $139 $90* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Maui - The Valley Isle

Paki Maui Oceanfront Resort

Condominium: Kaanapali, Maui

Affordable condominium resort on the Kaanapali Coast with lush tropical garden atrium, waterfall, and koi ponds.

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Travel: 06/01/2020 - 01/31/21
Rates from $149 $97* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Kamaole Sands Resort

Resort: Kihei, Maui

Conveniently located in Kihei, Kamaole Sands offers 1, 2-, and 3-bedroom suites directly across from the beach.

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Travel: 06/01/2020 - 01/31/21
Rates from $149 $97* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Polynesian Shores

Condominium: Lahaina, Maui

Polynesian Shores, a laid-back condominium resort edging the Pacific on West Maui’s legendary Kaanapali Coast.

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Travel: 06/01/2020 - 01/31/21
Rates from $169 $110* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Molokai - The Friendly Isle

Molokai Shores

Condominium: Molokai, Molokai

Spacious one-and two-bedroom oceanfront condominiums conveniently located in Molokai’s main town of Kaunakakai.

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Travel: 06/01/2020 - 01/31/21
Rates from $99 $65* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Oahu - The Gathering Place

Waikiki Shore

Condominium: Waikiki, Oahu

The only beachfront condo resort on Waikiki Beach, steps from Waikiki's best shopping, dining, and activities.

Learn More
Travel: 06/01/2020 - 01/31/21
Rates from $185 $121* *Excluding Taxes & Fees
Book: Now - 05/31/2020

Waikiki Grand

Hotel: Waikiki, Oahu

Located steps from Waikiki Beach, this hotel features moderately-priced rooms with ocean or Diamond Head views.

Learn More
Travel: 06/01/2020 - 01/31/21
Rates from $109 $71* *Excluding Taxes & Fees
Book: Now - 05/31/2020

* Terms & Conditions:

  • Full payment of room (plus tax) and reservation processing fee are due upon booking.
  • Hilo Hawaiian Hotel, The ISO, and Waimea Country Lodge: Full refund for cancellations at least 24 hours prior to arrival.
  • For all other Castle Hawaii resorts We will provide a full refund for cancellations at least 72 hours prior to arrival.
  • Book With Confidence cancellation policies apply.
  • Offer applies to new reservations only.
  • Rate are non-commissionable.
  • Offer may not be combined with any other offer or discount.
  • Rates shown are subject to availability and do not include taxes and fees.
  • Standard fees apply.
  • Other restrictions may apply.