Where to Stay in the Florida Keys (5 Best Places, By a Local)

5 Best Neighborhoods & Areas to Stay in the Florida Keys

The Florida Keys are a chain of over 800 islands that stretch over 100 miles long off the coast of South Florida. Thankfully, there are only a few main islands that you should consider staying at. Key Largo is the northernmost island. As you go south, you’ll find Islamorada, Marathon, Big Pine Key, and then Key West. 

In this guide, I break down the best islands to stay on from North to South. So, come along to find the right island for you!

Key Largo

👉 Best Area For Outdoor Adventures | ✨ Best Key Largo Hotels: Playa Largo Resort & Spa • Bungalows Key Largo • Bay Harbor Lodge and Coconut Bay Resort

Staying in Key Largo provides access to all the outdoor activities that the Keys are known for, without the long drive. Key Largo is only an hour from Miami, but it feels like it’s a world away from the hustle and bustle. 

Key Largo is best for those who like long days out on the water and then getting back in time for happy hour and sunset. It’s also a great place to stay for families who like to spend their days kayaking, snorkeling, diving, or fishing. 

Playa Largo Resort & Spa is a Marriott property that offers a true resort experience with a pool right on the water and great on-site dining options. The Bungalows Key Largo elevates the resort experience further by being an adults-only all-inclusive. 

Bay Harbor Lodge and Coconut Bay Resort offers quaint rooms on a lush property. This resort sets itself apart with fantastic service and free perks like kayaks, paddle boards, and daily freshly baked scones.

Pros of Staying in Key Largo:

• Close to Miami
• More affordable prices
• Easy access to outdoor activities

Cons of Staying in Key Largo:

• Far from the Lower Keys
• Limited nightlife
• Beaches can be rocky with darker water
• Town is not scenic
  

Islamorada

👉 Best Area For Relaxed Vacations | ✨ Best Islamorada Hotels: The Islands of Islamorada • The Moorings Village • Islander Resort • Three Waters Resort • Amara Cay

Islamorada is 30 minutes south of Key Largo. Being here will make you feel like you’ve made it to the Caribbean with the crystal clear waters, palm trees, and artsy boutiques. Islamorada is the perfect place for a relaxed vacation. 

The Islands of Islamorada has suites and multi-bedroom villas to suit families. It also offers a plethora of activities, so you never have to leave the property. Amenities include boat dockage, paddle boards, kayaks, bicycles, a pickleball court, s’mores kits, and yoga, along with a pool and hot tub, of course.

The Moorings Village caters to luxury travelers who prefer to have their own villa by the water, while staying within walking distance of some of the best restaurants in the area. Meanwhile, The Islander Resort is a retro-turned-chic hideaway. Its long sandy beach is dotted with cabanas, and there’s a very insightful Keys History Museum on-site as well. 

The Three Waters Resort and Amara Cay are sister properties that were recently acquired by Marriott and have just undergone a full renovation this past year. Be one of the first to stay at this refreshed hotel with multiple eateries and a water view!

Pros of Staying in Islamorada:

• Clear Water, Sandy Beaches
• Great Restaurants
• Nice areas to walk and bike

Cons of Staying in Islamorada:

• Can be pricey
  

Marathon

👉Best Area For Families & Boaters | ✨Best Marathon Hotels: Hawks Cay Resort • Isla Bella Beach Resort • Marlin Bay Resort & Marina

Marathon is loved by locals and known for its small-town vibes and relaxed attitude. Tiki bars abound in this area, and most visitors only pass through on their way to Key West. But Marathon is worth staying in, and I especially recommend it for families and boaters.

Hawks Cay Resort places special emphasis on activities for kids, making it a great place to stay for families. Isla Bella Beach Resort offers a more adult focus with the same resort-style amenities. 

Marlin Bay Resort & Marina is the perfect place to come if you have a boat or plan on staying on your boat. Amenities like showers, a pool, and a sauna make it very comfortable to overnight on your boat at Marlin Bay’s secure marina dockage. They also offer multi-bedroom units that make it easy to bring your whole family.

Pros of Staying in Marathon:

• Midway in the Keys
• Relaxed atmosphere
• Great boating and fishing
• More affordable restaurants
  

Cons of Staying in Marathon:

• Far from major attractions
  

Big Pine Key

👉 Best Area For Low-Key Travelers | ✨ Best Big Pine Hotels: Sugarloaf Key Hotel • Parmer’s Resort • Little Palm Island Resort & Spa

Staying in the Big Pine Key area probably means you are Key West bound, but budget conscious, or just looking to get away from it all. Here, you’ll be far away from attractions in the rest of the Keys, but only around 20 minutes to Key West.

Vacation rentals abound in Big Pine Key, so get a group together to split the cost! If you have an RV, drive it down the Florida Keys Scenic Highway and spend some time at one of the RV parks to enjoy amenities at a great price. One such place is Sugarloaf Key Hotel, which also offers rooms. 

Parmer’s Resort may seem no frills at first glance, but it delivers on what really counts: customer service, breakfast, and key amenities in a quiet area.

On the other hand, head to Little Palm Island Resort & Spa for a decidedly luxurious stay. Board their boat to arrive at the resort, and get swept away by the air of exclusivity. It’s the perfect place to unplug!

Pros of Staying in Big Pine Key:

• Many home rentals and RV parks available
• Close to Key West and Bahia Honda State Park
• More affordable than Key West
  

Cons of Staying in Big Pine Key:

• Requires a commute from long nights out in Key West
• Far from attractions in the Upper Keys
• Lack of options for mid range accommodations
  

Key West

👉Best Area For Nightlife & History | ✨Best Key West Hotels: Pier House Resort & Spa • The Mansion on the Sea • Andrew’s Inn & Garden Cottages • Ella’s Cottages

Key West has a reputation for its hard partying ways, pirate history, and historical significance, among other things. 

Key West is unlike anywhere else in the Keys due to its grid layout of narrow streets and small Queen Anne-style mansions. Over 200 years of hardy sailors, followed by waves of businessmen and creative types, have given Key West a multitude of landmarks. Stay near Duval Street to be near them all. 

Right at the beginning of Duval Street is the Pier House Resort & Spa, which on top of its great location also boasts its own private little beach. It’s a true haven in this sometimes congested part of town. 

All the way on the other, more quiet end of Key West, is The Mansion on the Sea, right near the Southernmost point buoy. One reviewer said it best, “We felt like we were visiting our rich, extended family in the midst of the Gilded Age.” It’s a picture perfect mansion with a Key West touch and a colorful paint job with wide open views of the ocean. 

If you prefer to be somewhere close to Duval, but set back a block or two from the revelry, then consider staying at boutique hotels like Andrew’s Inn or Ella’s Cottages. Hospitality takes the forefront at these quaint hotels with garden pools and breakfast. 

Pros of Staying in Key West:

• Plenty of attractions for every age and interest
• Variety of restaurants and bars
• Great nightlife
• Unique architecture and history
  

Cons of Staying in Key West:

• Can be busy and congested, particularly if a cruise ship is in port
• Can get rowdy, especially during some holidays
• Long drive to get there from Miami
  

Tips for Staying in the Florida Keys

Expect Traffic

There is only one road in and out of the Florida Keys, and while it is rarely at a standstill, it is often congested. Expect more major delays around holidays and weekends. 

Get Out on the Water

Although there are plenty of activities to do on land, the real magic of the Florida Keys is getting out on the water. It astounds me how many people come to the Keys and never get on a boat. Take that sunset cruise, snorkel tour, dive lesson, jet ski rental, and anything else you may get the opportunity to do! Otherwise, you really haven’t seen the Keys.

If you don’t know where to start, I recommend checking out Florida Keys tours on Viator!

Bring or Buy Snorkel Gear

See fish and other sea-life while at the beach without having to rent gear. For the cost of one or two rentals, you can buy your own mask and snorkel online or at any dive shop.

Know that the Keys are Fishing Villages at Heart

Don’t expect everything to be perfectly manicured or to experience great service all the time. The Florida Keys was mostly developed in the early 70s and has pretty much stayed that way due to development restrictions. It’s part of its charm, but the area has its quirks, too. Just blame it on island time.

Be Flexible

We are lucky to experience mostly sunny weather here in the Keys. However, sometimes tropical systems can bring wind or showers. Leave some extra time in your schedule to rearrange your activities in case the weather gets in the way.

FAQs about the Florida Keys

What are the best areas to stay in the Florida Keys for first-timers?

Islamorada and Key West are the best areas to stay in the Florida Keys for first-timers. Islamorada offers a central base to explore the best of the Keys. Key West offers a variety of restaurants and attractions that will appeal to everyone, and is a must-visit.

What are safe areas to stay in the Florida Keys?

Everywhere is very safe. The Florida Keys has a small town feel where many don’t even feel the need to lock their doors. The only area of concern is to generally be vigilant when out late due to impaired driving.

What are the best parts of the Florida Keys to stay on a budget?

Stay in Key Largo if you are interested in exploring the Upper Keys, or Marathon to explore the Lower Keys if you’re on a budget. 

What are the best parts of the Florida Keys to stay with kids?

Stick to a resort with lots of activities like Hawks Cay or a property with villas like The Islands of Islamorada or Marlin Bay.

What are the best parts of the Florida Keys to stay for couples?

For a romantic getaway, unwind in the quiet Lower Keys at Little Palm Island Resort & Spa or keep it simple with the all-inclusive Bungalows Key Largo. In Key West, I recommend the centrally located Pier House. 

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There are plenty of places to stay in the Florida Keys for adventure lovers, party goers, romantic couples, and young families. Now that you’ve figured out where to stay, read my recommendations for fun things to do in the Florida Keys.