Historic Tours In Key West
Youll find the Key West is one of the most historic towns in Florida, and as such there are lots of types of historic tours. I talked above about audio tours being the more affordable Florida Keys tour option, but if thats not your style, you can always book something more personal.
Expect to pay $20-$50 per person for different types of walking or tram tours in Key West. We live in Saint Augustine, the oldest city in the USA, and have lots of our visitors do guided tours in town, and the MOST POPULAR is always the ghost tour. And yes, Key West has ghost tours too. You can book a private walking tour of Key West for your group too, and that saves quite a bit versus paying for individual tickets.
Hop-on-Hop-off tours are a great way to explore towns without your own car . Key West has both the Conch Train and the Old Town Trolley for this. The Conch Train only has a few stops that you can get on and off, but the history and stories are great. The Old Town Trolley covers the whole town and has lots more boarding options. They also do the Ghosts and Gravestones tour.
Finding A Budget Key West Hotel Or B& b
Even in the summer off-season, your first search for basic Key West motels will come up with rooms starting at least $250 a night. Ive tried several strategies to beat that price some successful some not.
What didnt work very well: I used name your own price on Priceline twice in Key West. Both times I ended up in the eastern part of Key West, three miles from Old Town. There are eight or 10 hotels clustered on Roosevelt Boulevard at the entrance to Key West. They share a shuttle service into Old Town, which helps with parking.
The problem here is that the location isnt ideal and the price included add-on fees a $10 resort fee at the run-down Lexington and a $20 parking fee at the very nice Marriott Key West Beachside Hotel.
I had better luck finding accommodations in Key West where I compromised on amenities. One of the great charms of Key West is the historic bed and breakfasts in Old Town. Most go for $300 to $400 a night. But there are a few quality places where several bedrooms share a common bathroom, and the savings are great.
Americans love their plumbing, but if you can share a little as frugal travelers do elsewhere in the world you can stay in Key Wests Old Town at a great B& B.
We stayed at the Key West Bed and Breakfast, 415 William Street, Key West, a turn-of-the-century house decorated with original art, vibrant color and serving a spectacular breakfast of fresh fruits and homemade blueberry coffee cake.
Contact Information All Travelers
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Islamoradas 3 Best Places To Stay
Islamorada is stretched across numerous islands, so youll need to bring or hire a car to get the full experience. Theres a large bridge connecting all the islands, with the mainland in one direction and Key West in the other. It takes around two and a half hours to drive from one end of the Florida Keys to the other, with Islamorada located roughly in the middle.
Plantation Key is the first island youll discover when driving through Islamorada from the mainland. For families, this island offers peaceful vibes alongside family-friendly attractions. With laid-back theme parks and a wide variety of restaurants, youll be spoiled for choice on Plantation Key. Its also known as the creative heart of the Florida Keys, with art communes and galleries found everywhere. For the purpose of this guide, weve included Windley Key with this area, as theyre both well connected.
Heading further along the road, you will hit Upper Matecumbe Key. This island is a little bit livelier than Plantation Key, offering first time visitors the chance to really explore the region. Its also the most central area of Islamorada, so youll be well placed for exploring the region throughout your stay.
Still undecided? Its a tricky choice to make, but weve got some more advice about each area below to help you narrow down your options. Weve included our top picks for where to stay in Islamorada, and things to do in each to make your planning that little bit easier.
Lower Matecumbe Key Where To Stay In Islamorada For Couples

The final island within the Islamorada chain, Lower Matecumbe Key has an even more peaceful atmosphere. This island is also more adult than the others, making it our top pick for couples visiting the region. Youll get to enjoy fancy restaurants and some gorgeous sunset views.
Its also marginally the most affordable island. Youll still have to careful if youre travelling on a budget, but there are plenty of great deals on accommodation here. This is especially true during the offseason, so keep this in mind when planning a winter getaway.
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Southside Resort & Key West International Airport
Key Wests Southside Resort area is located on the southeastern edge of the island, next to the airport.
This tourist development is home to some big-name chain resorts and a few local hotels and privately-owned apartments.
Some of the attractions in this area include Fort East Martello Museum, an 1800s brick fortress and local history museum, a few beaches, and lagoons. This is also where the airport and the Greyhound Station are located.
Key West International Airport occupies the southern half of the islands east side. This local airport offers a wide range of domestic connections to the US South and the East Coast.
Accommodation in this area
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You Just Want To Escape The City: Key Largo
The unofficial grand entrance to the Florida Keys, Key Largo is just an hour south of Miamibut when you get there, you feel like youre in a whole other world. In quiet Key Largo, life is all about the water. Its bordered by Florida Bay and the Atlantic Ocean, and its home to John Pennekamp Coral Reef State Park, which is a part of the Florida Keys National Marine Sanctuary and home to the oldest underwater preserve in the U.S. Its both the longest key and a hub for South Florida water sports, so go here for scuba diving, snorkeling, sport fishing, dolphin encounters, kayaking, paddle boarding, boating and more.
Where to stay: Get comfy at Playa Largo, a luxury Autograph Collection hotel at Mile Marker 97 that fuses the modern conveniences of the Magic City with that je ne sais quoi about the serene Florida Keys. As soon as you walk in, the valet attendant will hand you one of the hotels signature pineapple mojitos. From then on, trust us: Youre in paradise.
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Islamorada Where To Stay In Florida Keys On A Budget
Pams Pics
- COOLEST thing to do in Islamorada Sportfishing this set of islands is known as the Sports Fishing Capital of the world!
- BEST place to visit in Islamorada Keys History & Discovery Center for a thoughtful look at the history of the area.
If you like adventure and are trying to decide where to stay in the Florida Keys on a budget at the same time, then staying in Islamorada is your best bet. This chain of 6 islands is known more for sport fishing and outdoor activities than posh hotels and restaurants. So, if youre looking to pay more local prices and spend your time outdoors for free, youll have plenty of chances to do it here.
Florida Keys On A Budget: Best Affordable Tropical Fun
After several trips to the Florida Keys the biggest question we get is how to visit the Florida Keys for cheap. Whats an affordable hotel in Key West? or What key should we stay on for cheap? Heres a plan for an affordable Florida Keys vacation that is budget friendly and also tons of fun.
If were missing a topic or dont answer your question in this post about doing an inexpensive Florida Keys trip, send me a note and Ill get you set up with the best budget information possible.
What you’ll find…
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Things To See And Do In Lower Matecumbe:
- Habanos Oceanfront Dining has casual vibes, gorgeous views, and a simply unmissable Cuban food and drinks menu.
- White Marlin Beach Park is the main beach on the island, offering laid-back vibes and secluded spots where you can soak up the sea breeze without the big crowds.
- Head to Saltwater Fly Guide, which offers some of the most affordable fishing charter options in the Florida Keys.
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Cheapest Places To Visit In Florida
Are you planning a Florida trip and looking for the cheapest places to visit in Florida? No wonder. The Sunshine State of the US has a lot to offer with a wide variety of places that can be traveled on a budget.
Florida is a dream holiday destination for many beach lovers. If you can do proper homework, avoid tourist traps and bad deals trust me, affordable vacation in Florida is not a hard job.
Check out our ultimate Florida checklist of the best and cheap weekend getaways in Florida including everything budget travelers need to know to make their cheap Florida travel a success.
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For An Active Beach Holiday

- Coconut Palm Inn is a beautiful beachfront hideaway at the southern tip of Key Largo, with 19 opulently-decorated rooms and suites. Pick this place for its secluded, small hotel feel, as well as the wealth of acitivites on offer for the whole family. Try paddle boarding, fishing, beach games and cycling, before rounding off the day with a big beach barbecue! Great for guests of all ages.
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There Is No Place Like The Keys
There is no place like the Keys. It has good old-fashioned fun for all and hopefully, it will stay that way. Islamorada is a two lane highway barely surrounded by land. It is not too commercial, nor is too residential. The outdoor restaurants with views are laden with the word vacation written between every line on the menu. The prices are out of line lately for many of the establishments. That will price them out of the interest market for many, and the blue collar vibe will decrease their appeal for the rich and famous, but hopefully prices will come down to semi-reasonable again soon and the upscale establishments will be kept to a minimum.
- From $359 per night7.9Good313 reviews
The location and views cant be beat. The sunrises were spectacular. Perfect spot for a couples vacation. I saw a few comments about the water being dirty or the beach not being a real beachif youve ever been to the keys you know that beaches are rare and to bring water shoes . The water was very clean and clear, there is just vegetation in some spots because, again, its the keys! We rented a tandem kayak and paddled to the sandbar, it is pretty close to the hotel. They are still working on renovating their villas but the main hotel buildings are all fully redone from the hurricane. The staff was very friendly and accommodating. We will definitely be back!
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Cheap Places To Stay In Islamorada Fl
Compare 4,548 available oceanfront holiday vacation home properties, starts from $33
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Why We Recommend This Hotel
Suppose you want to try all of the available water-based activities when you visit Islamorada. It might be difficult to achieve, but the Caribbean Resort strives to push you well toward that goal.
Its alright even if you have no prior experience when it comes to fishing. Just borrow the fishing rods on the property to test your luck if you can catch marlin, sailfish, yellowtail, and many more. Trust me, the fulfillment youd get afterward would be incomparable.
You can also freely use the paddleboards and kayaks for your fun activities throughout the day. Consider renting a boat if you still cant get enough of the ocean.
Do you plan to stay longer in paradise? You dont need to look anywhere else since this resort has dedicated homes for an extended staybe it weeks or even months.
Yes, the Caribbean Resort might not be a cheap place to stay but you can definitely get your moneys worth here.
Top Key West Dining Picks
One of our favorite restaurants in the Florida Keys is in Key West. El Siboney Cuban Restaurant is absolutely awesome, and they have two locations, one in the neighborhood on Catherine Street and one on Stock Island at the east edge of Key West. Im just going to list off the things you need to order: ham croquetas, roasted pork, Cuban sandwich, anything that comes with maduros , and you MUST have the guava cake.
No matter your dining style, El Siboney is our top dinner pick in Key West, and its just a bonus that its wonderfully budget friendly. The service is great and the food is top notch.
Moving on though, we also really enjoy Harpoon Harrys. Its located across from the Marker Key West and the Historic Seaport. They make incredible fried chicken and their fish tacos are some of the best in the Keys.
Another favorite for grab and go, but a bit pricier is the Fishermans Cafe. Its also in the Historic Seaport area and is walk up window only. They have some stand-up seating, but you should plan on taking your awesome fish sandwich with yucca fries to-go.
Our last pick, and its a stereotypical tourist pick is Blue Heaven. It really is great, and I felt absolutely justified in getting Bananas Foster for breakfast there. Good value for the quality and portions, and to make it better, there are chickens running around in the outdoor dining space. Love it!
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Key West Best Area To Stay In Florida Keys For Nightlife
- COOLEST thing to do in Key West Relax on the beach or enjoy some water sports at the Fort Zachary Taylor Historic State Park
- BEST place to visit in Key West Visit the Ernest Hemingway Home and Museum to learn about the islands most famous resident
Youve probably heard of Key West, most people have. This island is at the southernmost tip of the Keys and was built on the back of cigar-making, as well as money taken from shipwrecks. As a result of this history, the island is filled with beautiful mansions and cottages in white and pastel colors, but its still a laidback and relaxing area to visit.
The city is welcoming to everyone, offering everything from expensive restaurants to hidden dive bars. This is what makes staying in Key West ideal when youre deciding where to go in the Florida Keys for nightlife.
I’ve Been Diving Out Of Islamorada Since 1989
I’ve been diving out of Islamorada since 1989. It is about half wat to Key West which make it an idea location. Great dive shops, great restaurants and great place to stay. From all I’ve seen over the years it is also and great place to charter a deep sea fishing trip. However, like everywhere in the Keys accommodations are way, way too expensive.
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Florida Keys Vacation Rentals And Airbnbs
Because the Florida Keys is such a fun, desirable destination, booking a vacation rental or AirBNB in the Keys may be more complicated. Minimum night stays are very common and accommodations for just a couple vs a family are more difficult to find.
As you search for vacation rentals in the Florida Keys youll typically find multiple rooms for multiple nights, making any booking several hundred dollars. Unless youre a large family that would normally get two or more hotel rooms, youll be spending significantly more each night for a vacation rental in the Keys.
Planning a group trip is really smart though and perfect to turn a trip into an affordable Florida Keys vacation on a budget friendly trip. Between being able to split the cost of a Florida Keys vacation rental AND being able to split the cost of tour charters youll be able to lower the total cost per family significantly!