Northside Resort Vacation Packages
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Top Holiday Package Deals in Northside Resort
Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
CA $1,400
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Two concerns:
1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result.
2) concern may be equal parts
Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.
Reviewed on Sep 1, 2026
Ella's Cottages - Key West Historic Inns
Old Town Key West
CA $1,627
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (494 reviews)
It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.
Reviewed on Sep 1, 2026
Ridley House - Key West Historic Inns
Key West Historic District
CA $2,306
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (951 reviews)
Stayed here for a birthday celebration and it was perfect. Breakfast by the pool every morning, rooms were big, and we didn't hear anything throughout our stay so we slept well!
Reviewed on Sep 2, 2026
Where to stay in Northside Resort
Find the best Northside Resort areas and neighborhoods for the activities you enjoy most. Learn more about Northside Resort
Old Town Key West
4 out of top 10 points of interest in this area
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
2 out of top 10 points of interest in this area
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Northside Resort Hotel Deals
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $141
CA $203 total
Sep 3 - Sep 4
includes taxes & fees
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
CA $183
CA $286 total
Sep 15 - Sep 16
includes taxes & fees
Courtyard by Marriott Key West Waterfront
3031-41 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $221
CA $249 total
Sep 3 - Sep 4
includes taxes & fees
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
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
CA $109
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.