Where to Stay in the Florida Keys: Breakdown by Key!

With constant sunshine, unbelievably blue water, and endless adventure activities, the Florida Keys are a dream destination! But deciding where to stay, with over 10 major keys to choose from, can feel a little overwhelming.

As a native Floridian who grew up visiting the Keys (and even got married there), I’ve had the opportunity to explore this slice of paradise from Key Largo to Key West, and everywhere in between. I’ve stayed everywhere from no-frills motels and scuba lodges to high-end resorts with beachfront spas and private lagoons.

In this guide, I break it all down, by area and by travel style, so you can easily find the perfect place to stay, no matter your budget or vibe! Luckily, there are plenty of accommodations to choose from in the Florida Keys, and I’ll help you find the best one or you!

Quick Look: Best Hotels in the Florida Keys

Don’t want to read the whole post? Here’s a quick list of my top hotel recommendations by area of the Keys!

• Key Largo:
  • Holiday Inn Key Largo ($): Budget-friendly with great location near the marina.
  • Bakers Cay Resort ($$): Family favorite with private beach and two pools.
  • Playa Largo Resort & Spa ($$$): Modern resort with spa, fitness, beautiful pool, and restaurants.
  • The Bungalows ($$$$): Adults-only, all-inclusive luxury experience.
• Islamorada:
  • Island Bay Resort ($): Quaint, affordable cottages on the bay.
  • Islander Resort ($$): Recently renovated, great for families and couples.
  • The Caribbean Resort ($$$): Best for larger groups or extended families.
  • Cheeca Lodge ($$$): Luxurious, romantic, and right on the beach.
• Marathon
  • Rainbow Bend Resort ($): Charming, old-school vibes at a great price.
  • Hawks Cay Resort ($$): The ultimate family-friendly resort in the Middle Keys.
  • Isla Bella Resort ($$$): Chic, upscale, and beachfront with amazing pools.
• Big Pine Key:
  • Vacation Rentals or Camping: Limited hotels, best for RVers or Airbnb lovers.
• Key West:
  • Old Town:
    • Almond Tree Inn ($$): Boutique adults-only inn, steps from Duval.
      Hyatt Centric Key West ($$): Waterfront resort with a pool and perfect Old Town location
    • Pier House Resort ($$$): Great location + private beach.
    • Casa Marina ($$$$): Newly renovated luxury with the largest private beach.
  • New Town:
    • Havana Cabana ($$): Fun, Cuban-inspired and affordable.
    • Margaritaville Beach House ($$): Across from Smathers Beach, family-friendly.
    • Doubletree by Hilton ($$): Resort-style with free shuttle to Old Town.

Where to Stay in Key Largo

Now that you have understanding of the layout of the Keys, let’s break down the top hotels and places to stay in each area, starting with Key Largo!

Key Largo, often called the “Diving Capital of the World,” is the first Key you’ll reach when driving down from Miami.

For this reason, it’s a very popular spot for day trippers or Florida locals looking for a weekend getaway, since the drive from Miami to Key Largo is only about an hour!

Key Largo is known for its incredible snorkeling and scuba diving, thanks to the famous John Pennekamp Coral Reef State Park. If your priority is to get out on the water, Key Largo is a great choice!

When we visit the Keys, we love staying in Key Largo since it’s a quicker drive from Orlando and has some of the best underwater landscapes in the entire archipelago!

Moderate Option in Key Largo: Playa Largo Resort & Spa

For those seeking a luxurious experience, Playa Largo Resort & Spa is an excellent choice! This waterfront resort has some incredible features like an infinity pool, private cabanas, and fire pits on the beach.

In addition, they have personal training classes, tennis courts, a basketball court, and a tree-lined jogging trail on property. Plus the gorgeous Ocean Spa that offers a variety of tropical treatments!

Playa Largo also has four different restaurants to choose from, the most popular being Sol by the Sea!

I’ve had the pleasure of staying here a few times, and it is always a wonderful experience! This is the type of hotel where you won’t want to leave the resort! It’s perfect for couples or honeymooners too.

They have recently raised their prices, so it does lean a little more “luxurious” than “moderate” these days, but definitely worth it!

Ultra Luxury Option in Key Largo: The Bungalows

The Bungalows Key Largo is the only all-inclusive, adults-only resort in the Florida Keys. It features private waterfront bungalows, spa treatments, gourmet dining, and endless ocean views.

Your stay includes unlimited dining at 5 restaurants, premium alcoholic beverages, wines, and welcome drinks. In terms of amenities, there are two pools, kayaks, paddle boards, snorkel gear, group yoga classes, bikes, and more on property!

Although I’ve personally never stayed here, the reviews online speak for themselves! This is the epitome of luxury in the upper Keys.

Where to Stay in Islamorada

Next up in the Florida Keys we have the beautiful Islamorada!

Islamorada is my personal favorite part of the Florida Keys. We typically visit here once per year and my husband and I even got married here! I also grew up visiting Islamorada every 4th of July, and my dad went to high school here! So, it has a special place in my heart.

While I often refer to it as a key, Islamorada is actually a village made up of 6 different keys: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore islands of Indian Key and Lignumvitae Key.

Islamorada is known as the “Sportfishing Capital of the World” and is the perfect destination for those who love fishing, water sports, and snorkeling!

While Key Largo is the self-proclaimed “Diving Capital of the World”, in my opinion, Islamorada has some of the best snorkeling in the world, especially at the gorgeous Alligator Reef Lighthouse!

Islamorada is also home to Robbie’s, where their legendary tarpon feeding has become a must do on any Florida Keys itinerary.

Islamorada has a ton of different options for hotels, as well as some of the best restaurants in the Florida Keys!

Budget Option in Islamorada: Island Bay Resort

A great budget option in Islamorada is Island Bay Resort, a beautiful property without any crazy frills.

It is a very small and secluded resort with only 10 cottages on property. One caveat of staying here is the cottages only fit 2 people, and it is adults-only!

Each unit has a private deck, hammock, and kitchenette, plus there’s a small beach area for lounging or launching a kayak right into the bay.

Island Bay boasts an atmosphere designed specifically for adults seeking tranquility, romance, and relaxation!

Family-Friendly Option in Islamorada: Islander Resort

The Islander Resort, located in the heart of Islamorada, is one of the best places to stay in the Upper Keys for families! Recently renovated, the property is the perfect blend of laid-back Keys charm with modern amenities. A lot of people stayed here for our wedding and loved it!

Set on a sprawling, beachfront property, the Islander offers spacious rooms and suites with full kitchenettes, perfect for families or longer stays. The private beach is calm and shallow, making it great for kids, and there are two pools on-site, including one with a splash area.

The resort also has a putting green, pickleball courts, beach volleyball, and paddle boarding, as well as fun activities like movie nights and beachside yoga!

Overall, if you are looking for a family-friendly resort in Islamorada with tons to do on property, Islander is a great choice!

Large Group Option in Islamorada: The Caribbean Resort

The Caribbean Resort is hands-down my favorite resort in the Florida Keys. But I’m a little biased, since this is where my husband and I got married! I also grew up visiting this resort, so it feels like home to me.

The resort is truly more of a tropical getaway than a hotel. If you have a large group or family traveling to the Keys, the Caribbean Resort is the perfect option!

The resort has 22 individual, Caribbean-style homes on property that each fit between 4 and 10 people. We love visiting here as a family of 8 because we can all stay in one house with a full kitchen, washer and dryer, and multiple bathrooms.

Aside from the gorgeous houses, the resort also has a zero-entry pool and hot tub that feels like the ultimate luxurious escape. There’s also a marina, a long fishing dock, plus kayaks and bikes you can use!

I highly recommend staying at the Caribbean Resort if it fits your style and budget! Read my full guide to the Caribbean Resort here!

Luxury Option in Islamorada: Cheeca Lodge

Right down the road from the Caribbean Resort is the stunning Cheeca Lodge & Spa. If you are looking for luxury or romance, Cheeca Lodge is the spot for you!

The entire property is so lush and romantic feeling, with palm-tree lined paths lit by tiki torches. Some of their waterfront rooms even include a bathtub on the balcony! So glamorous.

There is also a private beach, a nine-hole golf course, tennis and pickleball courts, and a full-service spa on property.

For dining, there are several on-site restaurants to choose from. I also highly recommend driving across the street to Morada Bay or Pierre’s Restaurant, which are both on my list of the best restaurants in Islamorada!

➡️ For more options on where to stay in Islamorada, make sure to read my full guide: Best Hotels in Islamorada!

Where to Stay in Marathon

It’s time to move out of the Upper Keys and into the Middle Keys – with Marathon at its center! Similar to Islamorada, Marathon isn’t a key itself but a city that encompasses several keys!

Located in the heart of the Florida Keys, Marathon is a great place to stay for families and nature lovers. Some top places to visit here are the Turtle Hospital and the Dolphin Research Center.

If you’re looking to get out on the water, you can head to the famous Sombrero Beach and Sombrero Reef.

But my favorite part about staying in Marathon is getting to ride bikes across the Old Seven Mile Bridge and get incredible views of the new Seven Mile Bridge, which connects Knight’s Key to Little Duck Key!

While I’ve only visited Marathon a few times myself, I still have some top hotel recommendations!

Budget Option in Marathon: Rainbow Bend Resort

If you’re looking for a no-fuss, budget-friendly place to stay in Marathon, Rainbow Bend Resort is a great option that delivers more charm than you might expect at its price point. This old-school Florida Keys resort has a nostalgic vibe and offers a relaxed, low-key experience right on the ocean.

The resort features a variety of suites and cottages, many of which include kitchenettes, ideal for longer stays. Guests also enjoy complimentary breakfast each morning, a rare bonus for the Keys.

Rainbow Bend has a small pool, a hot tub, and its own private beach with lounge chairs for sunbathing. One of the best parts? Free access to kayaks, paddle boards, and bikes, making it easy to explore the surrounding area without spending extra!

Overall, this quaint resort is a great budget option in the heart of Marathon.

Family Friendly Option in Marathon: Hawk’s Cay Resort

Easily the most popular resort in the Middle Keys, Hawk’s Cay Resort is a destination in itself — perfect for families, couples, and even multi-generational groups.

Situated on its own private island (Duck Key), this massive resort offers everything you need for an unforgettable stay without ever having to leave the property.

The resort boasts 5 different pools, a private lagoon, a kids’ club, on-site dolphin encounters, and more! Parents can relax at the spa or poolside cabanas while kids enjoy fun activities.

There’s also several on-site bars and restaurants, plus a marina, water sports, and snorkel tours that leave right from the property! This resort has everything you need for an incredible stay in the Middle Keys.

Luxury Option in Marathon: Isla Bella Resort

If you’re looking for a more luxurious option in Marathon, you can’t go wrong with the stunning Isla Bella Beach Resort. Located at the foot of the famous Seven Mile Bridge, Isla Bella is a 24-acre resort with over 150 guest rooms, but it truly feels like so much more than a hotel!

On property, you’ll find 5 swimming pools (one of which is adults-only), a private beach, and a full-service spa!

They have one main restaurant, Mahina, as well as a burger spot by their main pool, both of which were absolutely to die for! I had the best burger of my life here, as well as a hogfish risotto I’m still dreaming about.

Although a bit pricey, this hotel is also a great option for families, as they have fun weekly activities like beach kickball, seashell decorating, gelato happy hour, and more!

They are also dog-friendly, which is a huge perk!

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Where to Stay in Key West

From key lime pie on a stick to thrilling water adventures to lively bars and restaurants, Key West is one of my favorite cities in the US! It’s the southernmost island in the Florida Keys, and the southernmost point in the contiguous USA.

Most people think of Key West when you say “The Florida Keys”, and its reputation does not disappoint!

When it comes to where to stay in the Key West, the island is divided into two main areas: Old Town and New Town.

Old Town is the historic heart of Key West, filled with Victorian-style homes, art galleries, and cultural attractions. This area is ideal for travelers who want to be close to iconic spots like Duval Street and Mallory Square.

However, this area is extremely compact, so aside from a few resorts, most accommodations are small and tucked away! Hotels and accommodations also tend to be pricier in Old Town since they’re located in the heart of town.

New Town, on the other hand, is located on the eastern side of the island, away from the hustle and bustle. New Town is much more spread out than Old Town, offering a quieter environment with modern accommodations (like free parking!).

It’s a great option for those who prefer more spacious and affordable lodging while still being a short drive from the action in Old Town.

➡️ For a more detailed breakdown on Key West hotels, make sure to check out my full guide on Where to Stay in Key West!

Hotels in Old Town Key West

Budget travelers might have a hard time finding affordable accommodation in Old Town Key West. There’s the NYAH Key West, which offers dorm-style accommodations with a trendy atmosphere. This is great for solo travelers or small groups looking to stick together with bunk beds.

In terms of family accommodations, I highly recommend the Hyatt Centric Key West for those that want to be in Old Town. This hotel is in a prime location, just steps away from Duval Street, Mallory Square and the Key Largo Historic Seaport. Make sure to check out the Conch Republic Seafood Company and Key West First Legal Rum Distillery nearby!

For moderate travelers, make sure to check out the Almond Tree Inn (adults-only) for a garden-style collection of bungalows.

Or, there’s the Pier House Resort, located right at the end of Duval Street near Sunset Pier and the historic Seaport. This resort has a private white-sand beach (which is rare for Key West), on-site restaurants, and a spa!

For luxury travelers, the Casa Marina Resort in Key West reigns supreme. I had the pleasure of visiting this hotel for a wedding and was blown away by its beauty. And it’s been renovated since then, so I can only imagine what it’s like now!

If you’re looking for the ultimate luxury, I highly recommend checking out their beachfront suites, which are on the ocean and have private lanais right on the beach. So incredible!

And if you have a group of people, consider checking out the many vacation rentals in Key West instead of a traditional hotel to help save money!

Overall, if you want to be walking distance to all the top things to do in Key West, Old Town is the place to be!

Hotels in New Town Key West

For New Town Key West, the options are much more traditional, but no less beautiful!

You’ll definitely be able to save some money by staying in New Town, so budget travelers will have more options, especially if you are staying in the off-season (like summer).

The adults-only Havana Cabana Hotel is a good option that’s normally reasonably priced! This Cuban-inspired hotel has some fun tropical flair like a yummy food truck and a mojito pool bar.

For families, a great choice is the Margaritaville Beach House, inspired by Jimmy Buffett! This resort is located right across from Smathers Beach, one of the best free things to do in Key West! They also have daily activities and games for both adults and kids alike!

Other options in New Town include the DoubleTree by Hilton Grand Key Resort, where we personally stayed the last time we visited Key West. This hotel is the perfect blend of tropical getaway and modern amenities. They also had a free shuttle to Old Town that really came in handy!

There aren’t too many luxurious properties in New Town. You’re better off staying in Old Town!

FAQs About Staying in the Florida Keys

Final Thoughts

As you can see, there’s no shortage of incredible hotels and vacation rentals to choose from in the Florida Keys!

Before choosing where to stay in the Keys, I recommend deciding what type of environment you’re looking for and activities you want to do and let that help guide your decision!

For underwater adventurers like me, you’ll probably be happiest in the Upper Keys, while partiers and foodies will be much happier in Key West!

However, I highly recommend planning a road trip from Key Largo to Key West so you can get a taste of everything!

Make sure to pin this post for future planning!