Key West Vacations


Plan your own Key West vacation package today


How many Key West vacations have you enjoyed? Whether you’re planning your first Key West trip or day dreaming of a return visit, here are some helpful tips and things to consider.

Key West is small – only 2 miles by 4 miles, so getting around is pretty easy. You could work with a travel agent, but it is also easy to plan your own Key West vacation package.

Key West International Airport

kw airport Welcome To The Conch Republic

Will you be flying into Key West Airport? Use the eyw airport code if you are booking your own flights online. The Key West Airport is small but there are many daily flights from a variety of destinations. There are many connections through cities such as Orlando, Ft. Lauderdale and Miami.

Driving to Key West – A1A

If you have time, making the drive from mainland Florida down historic highway A1A can be a lot of fun. This would be a great time to upgrade the rental car to a convertible and cruise with the top down. You’ll find many great places to stop along the way and some great panoramic views. It’s an easy drive and a perfect chance to unwind on your way to tropical Key West.

Boat to Key West

If you happen to find a great deal on flights to Ft. Myers, Florida, consider the Key West ferry on one of your Key West vacations. The boat is called the Key West Express and has regular trips which arrive daily in the historic Key West Seaport – walking distance to Duval, restaurants and hotels.

Key West Lodging

There are so many choices of accommodations on the island that it is worth taking multiple Key West Vacations just for the experience. Is your preference a romantic Key West bed and breakfast in the heart of Old Town? Or do you prefer a luxury Key West resort? Either way, there are plenty of options. Whether you are a sailor or a cruiser, there are plenty of Key West marinas in which to tie up for a few days. If you love the water, but didn’t bring your own boat to Key West, there are boats available to rent for lodging instead of staying in a hotel. If you are travelling with a larger group or just want a little added privacy, try one of the many Key West vacation rentals.

We have stayed at a both the Coral Hammock community and the Sanctuary at the Key West Golf Course. Both communities are excellent!

Curry Mansion Inn Exteirior left Our choice of Key West Bed and Breakfasts is the Curry Mansion in located on Caroline Street just one block from Duval. Free parking, excellent happy hour, full breakfast included and a great location. For more information click this Curry Mansion Inn link!
Curry Mansion Inn

Key West Car Rental

If any of your Key West vacations will include a rental car, there are a few rental car companies located at the Key West Airport. A few other rental companies are off site and will pick you up at the airport. We have rented cars in Key West both ways and prefer the convenience of renting a car with onsite pickup at the airport. There doesn’t seem to be a difference in price beyond the normal differences between companies. Check out the mykeywestvacation Key West Car Rental page for additional information on which companies offer on site locations.

Key West Taxi

If you need ground transportation, call the Five Sixes Cab company – aka Five 666666 Cab Company – Phone number: 305-296-6666.

Key West Activities


MacKen Kayak off of Higgs Beach

Kayaking at Higgs Beach

For such a small island, there sure is a lot to do! One of our Key West holidays was an eight day trip. During the first couple of days we felt like we had plenty of time to see and do some of our favorite Key West activities and attractions while mixing in visits to a few new places as well. By day 6 we were wondering where all the time had went!

Make the most of your Key west vacation. Plan your activities in advance – or at least start with a list of some highlights you would like to do. Remember though, you are on island time…Relax. There are so many great things to explore in Key West that you’ll need multiple Key West vacations to cover them all.

Key West Beaches

Amy and Noel Walking on beach wedding day

The Key West Beaches may be calling you if you are looking for a relaxing day in the sun. Key West Beaches are safe for young children as the waves are usually very small. A day at the beach can also be an affordable way to spend time in Key West. Most beaches are free of charge. The beach at Fort Zachary Taylor charges a small fee per car to enter the park while Smathers Beach and Higgs beach are open to the public at no cost.

Key West Restaurants and Dining

As I said earlier, Key West is a small island, but the number of dining choices is amazing. All Key West vacations should include a good mix of dining options. Most places on the island are casual including the restaurants. We suggest starting with the following guidelines:

Join The Locals:

Geiger Key Marina and Smokehouse or Hog Fish restaurant and Bar

Shrimp Boats by Hog Fish Horz


Take a walk around the marina near the Hog Fish bar and grill and the nearby fish market to experience this authentic sea port.

Water front:

Louie’s Backyard, Latitudes on Sunset Key and Sunset Pier

Duval Street:

You have to grab a burger at Fogarty’s and Cheeseburger in Paradise (Note: This is the original Cheeseburger in Paradise – Not the one owned by Jimmy Buffet- We like Jimmy’s version too, but there isn’t one in Key West)

Traditional Key West

Blue Heaven

Budget tip:

If you are traveling on a budget with a large family, consider renting a Key West condo or even staying at a hotel that includes a microwave and mini fridge. When we take our kids, we eat breakfast and many times lunch at the condo or around the hotel pool. Then we enjoy dinner out and add to our list of favorite places.

Key West Travel Updates

There you have it! Start with the basics and visit mykeywestvacation often for updates and more tips on planning your own Key West vacations.


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