Hawaii Island Pet-friendly Vacations

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Flight and Pet-friendly hotel deals in Hawaii Island

Price found within the past 48 hours. Click for updated prices.
Fairmont Orchid

Fairmont Orchid

CA $3,090
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip flight included
Montreal (YMQ) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,006 reviews)
Had an unbelievable stay in this place during the storm the staff were unbelievable area accommodation

Reviewed on Aug 17, 2026

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
CA $9,210
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip flight included
Montreal (YMQ) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 reviews)
Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

Don't see what you're looking for?
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5* Pet-friendly holidays in Hawaii Island

Price found within the past 48 hours. Click for updated prices.
Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
CA $9,210
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip flight included
Montreal (YMQ) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 reviews)
Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

3 Night Pet-friendly holidays in Hawaii Island

Price found within the past 48 hours. Click for updated prices.
Fairmont Orchid

Fairmont Orchid

CA $2,677
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,006 reviews)
Had an unbelievable stay in this place during the storm the staff were unbelievable area accommodation

Reviewed on Aug 17, 2026

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
CA $7,665
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 reviews)
Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

4 Night Pet-friendly holidays in Hawaii Island

Price found within the past 48 hours. Click for updated prices.
Fairmont Orchid

Fairmont Orchid

CA $2,466
per person
Sep 25 - Sep 29
found 19 hours ago
Roundtrip flight included
Edmonton (YEG) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,006 reviews)
Had an unbelievable stay in this place during the storm the staff were unbelievable area accommodation

Reviewed on Aug 17, 2026

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
CA $6,014
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 reviews)
Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

Pet-friendly Hotels in Hawaii Island

OUTRIGGER Kona Resort & Spa

OUTRIGGER Kona Resort & Spa

78-128 Ehukai Street Kailua-Kona HI
  • 51 min drive from Hawaii Volcanoes National Park
Book a stay at this golf resort in Kailua-Kona. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,190 reviews)
"We stayed 2 nights in an Oceanfront Room with Club Lounge access. The ocean view was breathtaking, and the Club Lounge host, Aunt Fua, was exceptional—warm, kind, helpful, and genuinely welcoming. She truly provided the Hawaiian hospitality. Unfortunately, several major issues overshadowed these ..."

Reviewed on Aug 18, 2026

OUTRIGGER Kona Resort & Spa
PACIFIC 19 Kona

PACIFIC 19 Kona

75-5646 Palani Rd Kailua-Kona HI
  • 1 hour drive from Hawaii Volcanoes National Park
Stay at this hotel in Kailua-Kona. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
8.4/10 Very good! (2,743 reviews)
"This place has everything you need: towels, umbrella, seats, bike, microwave, kettle and laundry area. Staff are helpful. Will go back again."

Reviewed on Aug 18, 2026

PACIFIC 19 Kona
Grand Naniloa Hotel Hilo - a Doubletree by Hilton

Grand Naniloa Hotel Hilo - a Doubletree by Hilton

93 Banyan Dr Hilo HI
  • 1 hour drive from Hawaii Volcanoes National Park
Book a stay at this golf resort in Hilo. Enjoy free WiFi, a golf course, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very good! (1,377 reviews)
"We stayed as a family of three, but all the teas and coffees and water bottles were prepared for two."

Reviewed on Aug 16, 2026

Grand Naniloa Hotel Hilo - a Doubletree by Hilton
See all 7,250 properties in Hawaii Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Deluxe Snorkel & Dolphin Watch

4.5hr Snorkel & Dolphin Watch includes breakfast & Lunch plus a 20ft slide

CA $159
per adult
96% of travellers recommend
4.5hr Snorkel & Dolphin Watch includes breakfast & Lunch plus a 20ft slide
Kona Catamaran Sail aboard Spirit of Aloha from Honokohau Harbor

Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha

CA $125
per adult
96% of travellers recommend
Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha
Young girl holding a sea urchin on the glass bottom boat in the Pacific Ocean near the Big Island of Hawaii

Glass-Bottom Boat Tour in Waikoloa

CA $70
per adult
94% of travellers recommend
Glass-Bottom Boat Tour in Waikoloa
See all activities in Hawaii Island

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.