Northside Resort Vacation Packages 2026 from $824

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The Latest Northside Resort Vacation Packages

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

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$824

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (981 reviews)

Great stay 2nd year in a row! This time I enjoyed the bar and specialty drinks! Staff excellent as well!

Reviewed on Aug 28, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$900

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,389 reviews)

Great property and staff

Reviewed on Aug 27, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,541

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$867

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (951 reviews)

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$867

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (493 reviews)

Perfect location, quiet, but a short walk to everything fun. And I. August heat in the Keys, the only walks must be short. Cottages are small but well laid out, with super comfy bed, cold AC and hotter than hot shower. Staff was awesome and the 3 pm happy hour by the pool was laid back. Breakfast wasn't fancy, but it was abundant. We will definitely be back.

Reviewed on Aug 29, 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

A white building with shutters, palm trees, and a lawn.

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.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

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.

A two-story house with green shutters and a wooden balcony.

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.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

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.

A sunset over the ocean with scattered clouds.

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

$133 nightly

$150 total

Sep 24 - Sep 25

Total with taxes and fees

8.2/10 Very Good! (2,361 reviews)

"This property was put together cheaply just so the owners could make a profit"

Reviewed on Aug 29, 2026

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

$191 nightly

$215 total

Aug 31 - Sep 1

Total with taxes and fees

9/10 Wonderful! (1,459 reviews)

"So spacious, perfect for groups. The room was very clean and the staff were helpful! 10/10 would stay again They were doing what seemed like a clorox cleaning of the common area sidewalks, which I thought would have been better scheduled during a week day when there werent many guests but other than ..."

Reviewed on Aug 28, 2026

Courtyard by Marriott Key West Waterfront

3031-41 N Roosevelt Blvd Key West FL

$159 nightly

$179 total

Aug 30 - Aug 31

Total with taxes and fees

See all 2,756 properties in Northside Resort

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.