Lower Florida Keys Vacation Packages 2026 from $1,028

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Your Lower Florida Keys Vacation

With a Lower Florida Keys vacation package, you can forget about the hassle of planning and instead focus on experiencing everything this amazing destination has on offer. Your trip to Lower Florida Keys wouldn't be complete without experiencing some of its most well-known cities, starting with Key West. Two of the top attractions here include Smathers Beach and Mallory Square. Cudjoe Key is another favorite with Lower Florida Keys travelers. Visitors to this city love Florida Keys Beaches and Sugarloaf Beach. When it's time to stop dreaming and start discovering, Expedia will help turn your Lower Florida Keys vacation into a reality.

The Latest Lower Florida Keys vacation packages

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,028

per person

Feb 1 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

i love the property, only bad thing was not pet friendly 😩

Reviewed on Dec 18, 2025

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,185

per person

Feb 19 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on Dec 12, 2025

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,052

per person

Feb 1 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Beautiful grounds, a lot of activities to do

Reviewed on Dec 19, 2025

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,438

per person

Feb 19 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

I was only given a room upgrade after making a complaint before the stay (a link to a website did not work). Silly me but I was also unaware of the $52 per day “resort fee”. I probably could have parked on the street and avoided the $30 daily parking fee. The little fridge took some figuring to lower the temp but after a couple of days it eventually went back up to 70 degrees all its own, so some food went bad and my cold drinks became close to room temp. The toilet was a wrestling match but that’s on me as I did not complain about it. The service in the restaurant was indifferent but the food was very good. I only ate there once. It’s not a bad place by any stretch but I doubt I’d return! Who knows?

Reviewed on Dec 17, 2025

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$2,461

per person

Mar 6 - Mar 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on Nov 20, 2025

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Where to stay in Lower Florida Keys

Find the best Lower Florida Keys areas and neighborhoods for the activities you enjoy most. Learn more about Lower Florida Keys

Old Town Key West

3 out of top 10 points of interest in this area

4.5/5(226 area reviews)

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.

Audubon House and Tropical Gardens featuring a house

Key West Historic District

2 out of top 10 points of interest in this area

4.5/5(4,033 area reviews)

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.

Discover the most popular places to visit in Lower Florida Keys

Duval Street

4.5/5(3,475 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.