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Hawaii (40 offers included)

Hawaiian Islands With Ocean View Upgrades
Value Vacation
from $4,194.00 (USD)
Per Person
Apr 09, 2026
through Jun 18, 2026
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 10
Price Per Night:$419.40 (USD)
(based on double occupancy, for comparison only)
Apr 09, 2026 through Jun 18, 2026
11 Days, featuring: Maui
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Hawaiian Islands
New, Value Vacation
from $3,264.00 (USD)
Per Person
Nov 13, 2025
through Nov 23, 2025
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 10
Price Per Night:$326.40 (USD)
(based on double occupancy, for comparison only)
Nov 13, 2025 through Nov 23, 2025
11 Days, featuring: Honolulu
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Hawaiian Islands
Value Vacation
from $3,784.00 (USD)
Per Person
Apr 09, 2026
through Jun 18, 2026
Offer Image
Cosmos logo
More offers from Cosmos
Nights: 10
Price Per Night:$378.40 (USD)
(based on double occupancy, for comparison only)
Apr 09, 2026 through Jun 18, 2026
11 Days, featuring: Honolulu
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Exclusive $200 in instant savings + Room & Breakfast package savings + More at Hyatt Regency Maui Resort & Spa
Jul 01, 2025
through Dec 20, 2025
Hyatt Regency Maui Resort & Spa
Delta Vacations logo
More offers from Delta Vacations
Jul 01, 2025 through Dec 20, 2025
Exclusive $200 in instant savings + Room & Breakfast package savings + More at Hyatt Regency Maui Resort & Spa
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Marriott Vacation Club, Waikiki
Hotel Rating: 4 stars
from $450.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$150.22 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Escape to the bustling city of Honolulu for warm sunshine and adventurous activities. Near Waikiki Beach, the Marriott Vacation Club®, Waikiki boasts luxurious and sophisticated vacation rentals for a fun and comfortable stay in Honolulu.
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Sheraton Kauai Coconut Beach Resort
Hotel Rating: 4 stars
from $448.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$149.56 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
This comfortable hotel provides easy access to a number of Kapaa's biggest hot spots, such as Smith's Tropical Paradise and Wailua Falls.
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Kiahuna Plantation Resort Kauai by OUTRIGGER
Hotel Rating: 3.5 stars
from $529.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$176.44 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Situated amid 35 acres of lush gardens bordering the sands of sunny Poipu Beach, these charming, cottage-style vacation condos are reminiscent of Hawaii's 19th-century plantation past.
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Montage Kapalua Bay
Hotel Rating: 4.5 stars
from $1,555.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$518.44 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Montage Kapalua Bay is an unparalleled collection of two- and three-bedroom luxury villas nestled on the shores of Kapalua Bay in northwest Maui.
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Maui Kaanapali Villas
Hotel Rating: 3.5 stars
from $397.00 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$132.33 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Set on 11 acres of exotic tropical gardens in the heart of the Kaanapali Resort area on one of the finest stretches of Kaanapali Beach.
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Kohala Suites by Hilton Grand Vacations
Hotel Rating: 4.5 stars
from $508.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$169.44 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Kohala Suites by Hilton Grand Vacations provides an unsurpassed vacation setting near the beach and championship golf courses.
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Royal Kona Resort
Hotel Rating: 3.5 stars
from $548.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$182.89 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Set oceanfront overlooking Kailua Bay in the heart of Kona, the Royal Kona Resort is within walking distance of restaurants, shops, historical sites, and activities.
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Mauna Lani Point
Hotel Rating: 4 stars
from $925.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$308.56 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
With an idyllic oceanfront setting, this gated community includes one- and two-bedroom accommodations featuring expansive living and dining areas, tasteful furnishings and private lanais.
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The Royal Hawaiian, a Luxury Collection Resort, Waikiki
Hotel Rating: 5 stars
from $549.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$183.11 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Opened in 1927 and known as the "Pink Palace of the Pacific," The Royal Hawaiian, a Luxury Collection Resort, Waikiki is an oasis of timeless luxury.
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The Ritz-Carlton Maui, Kapalua
Hotel Rating: 5 stars
from $896.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
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Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$298.89 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Just as Kapalua translates to "arms embracing the sea," the iconic AAA Five-Diamond resort The Ritz-Carlton Maui, Kapalua embraces guests with island-inspired luxury and natural aloha.
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Hawaiian Discovery First Class
from $5,925.00 (USD)
Per Person
Mar 28, 2027
through Apr 07, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 10
Price Per Night:$592.50 (USD)
(based on double occupancy, for comparison only)
Mar 28, 2027 through Apr 07, 2027
Get on island time as you discover Hawaii’s authentic tropical paradise, including Kilauea Volcano and Kauai's magical Tunnel of Trees and Waimea Canyon State Park. Tour Honolulu’s Pearl Harbor, relax in Kona, learn from locals how coffee is made and get a fascinating insight into manta ray conservation.
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Hawaiian Discovery Moderate
from $5,625.00 (USD)
Per Person
Jan 10, 2027
through Mar 28, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 10
Price Per Night:$562.50 (USD)
(based on double occupancy, for comparison only)
Jan 10, 2027 through Mar 28, 2027
Get on island time as you discover Hawaii’s authentic tropical paradise, including Kilauea Volcano and Kauai's magical Tunnel of Trees and Waimea Canyon State Park. Tour Honolulu’s Pearl Harbor, relax in Kona, learn from locals how coffee is made and get a fascinating insight into manta ray conservation.
More Details Contact Us
Best of Hawaii First Class
from $4,750.00 (USD)
Per Person
Mar 26, 2027
through Apr 04, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 9
Price Per Night:$527.78 (USD)
(based on double occupancy, for comparison only)
Mar 26, 2027 through Apr 04, 2027
Experience the best of Hawaii: the powerful waves of Oahu’s North Shore, Pearl Harbor and the USS Arizona. Learn about the importance of salt from Aloha Ambassador over a Be My Guest experience at Kona Salt Farm. You’ll forge an unforgettable connection with nature, from the black sands of Punalu’u Beach Park to a memorable visit to Volcanoes National Park.
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Napili Shores by OUTRIGGER
Hotel Rating: 3 stars
from $427.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$142.44 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Experience newly refurbished studios and one-bedroom condos in a private oceanfront setting. Every unit is fresh and new with custom furniture and bedding, plantation-style shutters, flat-screen LCD televisions and ceiling fans.
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Aston at Papakea Resort
Hotel Rating: 2.5 stars
from $403.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$134.56 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
This picturesque oceanfront condominium resort is nestled amid 13 acres of lush tropical landscaping and expansive lawns.
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Mauna Lani, Auberge Resorts Collection
Hotel Rating: 5 stars
from $1,191.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$397.11 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Nestled on a white-sand beach surrounded by lush tropical gardens and historic fishponds, the Mauna Lani, Auberge Resorts Collection promises an idyllic Island of Hawaii escape.
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Courtyard by Marriott King Kamehameha's Kona Beach Hotel
Hotel Rating: 3.5 stars
from $733.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$244.44 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
With a fabulous beachfront location in the heart of the historic fishing village of Kailua-Kona the Courtyard King Kamehameha's Kona Beach Hotel offers the perfect setting for a Big Island vacation.
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Aston Islander on the Beach
Hotel Rating: 3 stars
from $329.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$109.89 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
This charming, low-rise oceanfront resort, located at the Coconut Plantation Resort area, is just a short stroll away from the Coconut Marketplace's 60 specialty boutiques and restaurants.
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Wailea Ekahi Village
Hotel Rating: 3 stars
from $633.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$211.11 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Surrounded by lushly landscaped terraces that slope gently toward the Pacific, the Wailea Ekahi Village overlooks beautiful Keawakapu Beach.
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Best of Hawaii Moderate
from $4,495.00 (USD)
Per Person
Mar 26, 2027
through Apr 04, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 9
Price Per Night:$499.44 (USD)
(based on double occupancy, for comparison only)
Mar 26, 2027 through Apr 04, 2027
Experience the best of Hawaii: the powerful waves of Oahu’s North Shore, Pearl Harbor and the USS Arizona. Learn about the importance of salt from an Aloha Ambassador over a Be My Guest experience at Kona Salt Farm. You’ll forge an unforgettable connection with nature, from the black sands of Punalu’u Beach Park to a memorable visit to Volcanoes National Park.
More Details Contact Us
Hawaiian Discovery Premium
from $6,295.00 (USD)
Per Person
Mar 28, 2027
through Apr 07, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 10
Price Per Night:$629.50 (USD)
(based on double occupancy, for comparison only)
Mar 28, 2027 through Apr 07, 2027
Get on island time as you discover Hawaii’s authentic tropical paradise, including Kilauea Volcano and Kauai's magical Tunnel of Trees and Waimea Canyon State Park. Tour Honolulu’s Pearl Harbor, relax in Kona, learn from locals how coffee is made and get a fascinating insight into manta ray conservation.
More Details Contact Us
OUTRIGGER Waikiki Paradise Hotel
Hotel Rating: 4 stars
from $256.00 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$85.33 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Located one block to Waikiki Beach, in the heart of Waikiki's action, OUTRIGGER Waikiki Paradise Hotel is well suited for families with children.
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Hawaiian Explorer First Class
from $4,075.00 (USD)
Per Person
Mar 28, 2027
through Apr 04, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 7
Price Per Night:$582.14 (USD)
(based on double occupancy, for comparison only)
Mar 28, 2027 through Apr 04, 2027
Waikiki and Maui, Pearl Harbor and the volcanic energy of Hawaii Volcanoes National Park are yours to discover on this Hawaii tour. Sip a fragrant brew at a Kona coffee plantation and visit Punalu'u Beach Park - home to black sand and sea turtles basking in the sun - topped off with a classic Hawaiian luau.
More Details Contact Us
Best of Hawaii Premium
from $5,075.00 (USD)
Per Person
Mar 26, 2027
through Apr 04, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 9
Price Per Night:$563.89 (USD)
(based on double occupancy, for comparison only)
Mar 26, 2027 through Apr 04, 2027
Experience the best of Hawaii: the powerful waves of Oahu’s North Shore, Pearl Harbor and the USS Arizona. Learn about the importance of salt from Aloha Ambassador over a Be My Guest experience at Kona Salt Farm. You’ll forge an unforgettable connection with nature, from the black sands of Punalu’u Beach Park to a memorable visit to Volcanoes National Park.
More Details Contact Us
Waipouli Beach Resort & Spa Kauai by OUTRIGGER
Hotel Rating: 4 stars
from $617.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$205.78 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
The one- and two-bedroom suites at Waipouli Beach Resort & Spa Kauai by Outrigger feature one, two or three full, luxurious baths and a complete kitchen equipped with Sub Zero refrigerators and sleek granite countertops.
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Andaz Maui at Wailea Resort - a concept by Hyatt
Hotel Rating: 5 stars
from $985.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$328.44 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Andaz Maui at Wailea Resort is an experience unlike any other, redefining luxury with a non-traditional approach.
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The Westin Hapuna Beach Resort
Hotel Rating: 4.5 stars
from $654.00 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$218.00 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
This luxurious hotel is nestled on one of "America's Best Beaches" on the sunny Kohala Coast.
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Marriott's Waiohai Beach Club
Hotel Rating: 4.5 stars
from $729.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$243.11 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Set amidst lush greenery, beckoning pools, and swaying palm trees just steps from Poipu Beach, Marriott's Waiohai Beach Club offers an idyllic getaway.
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Hawaiian Explorer Moderate
from $3,875.00 (USD)
Per Person
Mar 28, 2027
through Apr 04, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 7
Price Per Night:$553.57 (USD)
(based on double occupancy, for comparison only)
Mar 28, 2027 through Apr 04, 2027
Waikiki and Maui, Pearl Harbor and the volcanic energy of Hawaii Volcanoes National Park are yours to discover on this Hawaii tour. Sip a fragrant brew at a Kona coffee plantation and visit Punalu'u Beach Park - home to black sand and sea turtles basking in the sun - topped off with a classic Hawaiian luau.
More Details Contact Us
Park Shore Waikiki
Hotel Rating: 3 stars
from $299.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$99.78 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
The ultimate location fronting world-famous Waikiki Beach and centrally located between Diamond Head and the excitement of Waikiki.
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Courtyard by Marriott Waikiki Beach
Hotel Rating: 3 stars
from $315.00 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$105.00 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Just steps from pristine white sand beaches and world-class shopping, Courtyard by Marriott Waikiki provides rest and relaxation from your island adventures.
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The Best of Hawaii
Land Journey
from $11,890.00 (USD)
Per Person
Nov 20, 2026
through Dec 01, 2026
Offer Image
Tauck logo
More offers from Tauck
Nights: 11
Price Per Night:$1,080.91 (USD)
(based on double occupancy, for comparison only)
Nov 20, 2026 through Dec 01, 2026
Special tropical Tauck touches await on our classic four-island tour across Hawaii - including ocean-view rooms at luxury beachfront resorts for 11 nights, private evening with an after-hours tour, reception and dinner at Queen Emma Summer Palace on the island of Oahu, a private catamaran sail at sunset on the Big Island, an ecology lecture on Kauai, and an early-opening visit to iconic Iolani Palace.
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The Ritz-Carlton Oahu, Turtle Bay
Hotel Rating: 4.5 stars
from $1,173.33 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$391.11 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
The Ritz-Carlton Oahu, Turtle Bay spans nearly 1,300 pristine acres on Oahu's North Shore, featuring five miles of untouched coastline and 12 miles of breathtaking trails.
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OUTRIGGER Reef Waikiki Beach Resort
Hotel Rating: 4.5 stars
from $395.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$131.89 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Find this Luxurious Oceanfront Hotel situated on one of the most coveted stretches of Waikiki Beach, Outrigger Reef Waikiki Beach Resort places you at the heart of Oahu's sun, sand, and spirit of Aloha.
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Hawaiian Explorer Premium
from $4,350.00 (USD)
Per Person
Mar 28, 2027
through Apr 04, 2027
Offer Image
Trafalgar logo
More offers from Trafalgar
Nights: 7
Price Per Night:$621.43 (USD)
(based on double occupancy, for comparison only)
Mar 28, 2027 through Apr 04, 2027
Waikiki and Maui, Pearl Harbor and the volcanic energy of Hawaii Volcanoes National Park are yours to discover on this Hawaii tour. Sip a fragrant brew at a Kona coffee plantation and visit Punalu'u Beach Park - home to black sand and sea turtles basking in the sun - topped off with a classic Hawaiian luau.
More Details Contact Us
White Sands Hotel
Hotel Rating: 3 stars
from $374.67 (USD)
Per Person
Oct 05, 2025
through Oct 08, 2025
Offer Image
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$124.89 (USD)
(based on double occupancy, for comparison only)
Oct 05, 2025 through Oct 08, 2025
Kick back with swaying palms, a Mai Tai around the pool, and a renovated room with lanai and cool island colors at the White Sands, a vintage walk-up hotel in the heart of Waikiki.
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