Six Tips for a Key West Trip on a Tight Budget

Enjoy Key West without Breaking the Bank

A luxury Key West vacation on a budget? Is that even possible?

With these six pro tips, it’s not only possible-  it’s as easy as Key Lime Pie. 

(Psst- there’s even FREE stuff!)

1.  Travel with a group of friends or family

Gather up a group of your old college buddies, a couple of your favorite co-workers, or consider a destination family reunion in Key West.  A group of about 8 to 10 people is the sweet spot for massive savings. More on this in a minute.

2.  Fly Direct… or Drive

A few airlines are now offering direct flights to Key West from major airports such as Chicago, Newark, Philadelphia, and Dallas.  

Flying direct means skipping the connection in Atlanta or Miami saving you $300- $600 depending on airline rates.  That’s a considerable amount of cash.

Or, if you’ve never driven the Overseas Highway, consider a road trip.  With bright sunshine and endless turquoise water on either side of you as you make your way over 140+ bridges, the journey itself is as dreamy as the destination.

3.  Skip the Hotel

On average, a tiny hotel room in Old Town Key West will cost you about $350-$650 per night in season.


Consider renting one of our sprawling, luxurious vacation rental homes, like the Duval Square Penthouse.

At first glance, you think “Nah, there’s no way I could afford that.”  Here’s where your group of pals comes in handy!

Rent the Duval Square Penthouse with seven of your friends, and you’ll be paying about $140 per night per person in season.  

Travel in the off-season of August or September and you’ll be spending about $90 per night.  Cha-ching!

Plus, an over-priced, cramped hotel room can’t offer you a fully-equipped kitchen, several private outdoor spaces, laundry facilities, a huge living area with a 70-inch television and four gleaming, spa-like bathrooms.  Duval Square Penthouse has all that and more.

4.  Dine In

When you first arrive on the island, take a quick trip to the grocery store and stock up on supplies, then prepare and eat breakfast in your fully stocked kitchen.  Gather the crew together at the farmhouse dining table and linger over a casual, leisurely lunch.

Saunter back from the Duval Square rooftop pool for a quick snack or a homemade cocktail.

When you aren’t forced to eat and drink at a restaurant for breakfast, lunch, and dinner- like you would at a hotel- the savings stack up quick.

5.  Free Stuff!

All completely free- all totally fun.

6.  Eat Cuban Food

Key West is just 90 miles from the city of Havana, Cuba.  Just for reference- the nearest Walmart is 140 miles away. Yup, Key West is closer to Cuba than it is to a Walmart.

Embracing the Cuban culture of Key West will not only add flavor and authenticity to your trip-  it can also save you big bucks on meals.

Cuban food is delicious and affordable- think juicy rotisserie chicken, spicy pulled pork, savory picadillo, sweet plantains, and the ever-present black beans and rice.  Get hooked on Cafe Con Leche ($2.75) and Cuban Cheese Toast ($3.50)- yummy, cheap, and a local favorite.

Try the Cuban Coffee Queen, Sandy’s Cafe, or El Siboney for some outrageously tasty and inexpensive authentic Cuban fare.

With these six pro tips, your Key West dream vacation is a lot closer than you think.