Beachside Vacation Packages

Photo by Carmen Bustin-Dinning

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Top Holiday Package Deals in Beachside

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

The Marker Key West Harbor Resort

Key West Historic District

CA $1,958

per person

Oct 31 - Nov 4

found 15 hours ago

Roundtrip flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

CA $3,908

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

CA $3,113

per person

Dec 19 - Dec 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.6/10 Excellent! (419 reviews)

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

CA $5,622

per person

Dec 5 - Dec 12

found 16 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

10/10 Exceptional! (1 review)

Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,267

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

A+

Reviewed on Sep 28, 2026

Where to stay in Beachside

Find the best Beachside areas and neighborhoods for the activities you enjoy most. Learn more about Beachside

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 Fort East Martello Museum and Gallery.

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.

Beachside Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $167

CA $268 total

Oct 7 - Oct 8

includes taxes & fees

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

CA $233

CA $366 total

Sep 30 - Oct 1

includes taxes & fees

8.6/10 Excellent! (3,636 reviews)

"A+"

Reviewed on Sep 28, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

CA $296

CA $422 total

Oct 5 - Oct 6

includes taxes & fees

See all 2,740 properties in Beachside

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.