Best Places to Stay in the Florida Keys For All Budgets

Planning a trip to the Florida Keys can be overwhelming. One of the most challenging parts is figuring out the best places to stay in the Florida Keys. You need to decide on not only your accommodation, but also which islands to stay on.

Below, I’ve created a detailed yet simple guide to help you decide where to stay in the Florida Keys – whether you choose to base yourself at one hotel, or you’re planning a longer road trip with multiple stops, like I did.

The Florida Keys: An Introduction to the Keys

In planning where to stay on the Florida Keys, your first task is to understand the geography of the keys and choose which islands to stay on.

Key = island.

Yes, this might seem like the basics to some of you, but it’s important to understand that the Florida Keys are so much more than Key West. Key West is just one key (island) out of many.

The Florida Keys are a string of tropical islands off the southern tip of Florida. Notably, they’re connected by a series of 42 bridges (AKA, engineering marvels).

This means that you can road trip the entirety of the Florida Keys, staying on various islands in different resorts or hotels along the way.

List of the Florida Keys (With Personalities)

Approximately 1,700 islands make up the Florida Keys but not all of them are habitable.

Of the most popular, habitable keys, each has its own vibe and personality, and will be better suited to some travelers than others.

These are the most popular Florida Keys to stay on (listed north to south):

• Key Largo: Nature, snorkeling, conservation, laid-back.
• Islamorada: Sport fishing, beach resorts, restaurants, tourists.
• Marathon: Relaxing, fishing, luxury resorts, diving.
• Big Pine Key: Quiet, rustic, off-the-beaten path, key deer.
• Key West: Cultural, irreverent, lively, historical, fun, southernmost point.

From Miami to Key West it takes about 3.5 hours driving (barring traffic) but why not split it up into a multi-day road trip? That way you can stay on multiple keys and experience the full variety of the Florida Keys.

Where We Stayed on Our Florida Keys Road Trip

I want to briefly share our own road trip itinerary with you, before I get further into my description of the best places to stay on each key.

A Florida Keys road trip is typically done from north to south and back, either with your own vehicle or by renting a car after flying into Miami, like we did. Alternatively you could fly into the Key West airport and rent a car there (but that option is much more expensive).

Miami > Islamorada > Key West > Marathon > Miami

Where we stayed in the Florida Keys on a 7-day road trip:

• Day 1: AC Hotel Miami Airport West (near Miami airport)
• Day 2: Postcard Inn and Resort (Islamorada)
• Day 3: Postcard Inn and Resort (Islamorada)
• Day 4: The Gardens Hotel (Key West)
• Day 5: The Gardens Hotel (Key West)
• Day 6: Isla Bella Beach Resort (Marathon)
• Day 7: Drove back to Miami and flew home.

Hopefully, our own itinerary gives you an idea of what a possible trip through the Florida Keys might look like, and where to stay along the way.

RELATED | The Perfect 5 Day Florida Keys Itinerary

Best Places to Stay in the Florida Keys – Divided by Island

Below is a more detailed guide to the best places to stay in the Florida Keys, with my hand-picked accommodation options for all budgets on the main islands.

I am covering the keys from north to south, to mirror a typical road trip.

Best Places to Stay on Key Largo

Key Largo is in the upper keys, and is the first island you hit on the Overseas Highway as you drive south into the Florida Keys from Miami. It’s most known for the John Pennekamp Coral Reef State Park, which is incredible for snorkeling and the first undersea state park in the country.

The general vibe of Key Largo is laid back, natural, and full of lots of fisheries and kitschy places to eat.

WHAT WE DID | We did not actually stay on Key Largo, in favor of nearby Islamorada. I would recommend picking either Key Largo or Islamorada, both in the upper keys, and exploring from there.

Bayside Inn ($) | Key Largo

Bayside Inn is a good option for those on a lower budget who want to stay in Key Largo. The casual inn has a private beach, pool, and is only a 5-minute drive from John Pennekamp Coral Reef State Park.

Book your stay at Bayside Inn here.

Island Bay Resort ($$) | Key Largo

Island Bay Resort is a 3-star beachside resort in Key Largo that gets absolutely phenomenal reviews, with a 9.6 rating on Booking.

The property is full of uniquely designed cottages, giving very Florida Keys vibes. You can even go snorkeling directly from their beach. This is my personal pick in Key Largo!

Book your stay at Island Bay Resort here.

Jules’ Undersea Lodge ($$$) | Key Largo

Jules’ Undersea Lodge is by far the most expensive place to stay in Key Largo (possibly, the Florida Keys) but let me tell you, it is one of a kind.

This hotel is literally UNDER WATER and you must scuba dive to reach it. You sleep overnight 22-feet underwater (starting from $1,350) and even get a pizza delivery for dinner. Talk about bucket list worthy.

Book your stay at Jules’ Undersea Lodge here.

See more places to stay in Key Largo here.

Best Places to Stay on Islamorada

Islamorada is also in the upper keys, but further south than Key Largo. It is a village that is spread across six keys and has a reputation that’s a bit more refined and touristy than Key Largo.

You’ll want to visit Islamorada for fishing charters and wonderful restaurants – I recommend dinner reservations at Chef Michael’s. There are quite a few accommodations on Islamorada, especially family friendly beach resorts (which I’ve picked the best of below).

WHAT WE DID | We stayed at Postcard Inn Beach Resort on Islamorada for two nights. I loved that we had direct access to the beach which we took advantage of with swimming, paddle boarding, and kayaking! More about this hotel below.

Sunset Inn ($-$$) | Islamorada

Sunset Inn is a 3-star accommodation in Islamorada that is a good option for low to midrange budgets.

Keep in mind, unfortunately nowhere in the Florida Keys is “cheap” however I am currently seeing deals for $125/night, and with an 8.6 star rating on Booking, swimming pool, free parking, barbecue, free bikes, and Netflix – that’s a good deal for Islamorada!

Book your stay at Sunset Inn here.

Postcard Inn Beach Resort ($$ – $$$) | Islamorada

Postcard Inn Beach Resort is where we stayed. This is a family friendly resort directly on the beach, with complimentary paddle boards, kayaks, bikes, and more available to guests. SO FUN!

Notably, this place is also famous because it’s where the rum runner cocktail was invented – you have to try one here! There are a few restaurants on site, as well.

Book your stay at Postcard Inn Beach Resort here.

Cheeca Lodge & Spa ($$$) | Islamorada

Cheeca Lodge & Spa is the best place to stay for luxury in Islamorada. The scenery and amenities are incredible: 1,000 feet of beachfront, a 9-hole golf course, 525-foot fishing pier, spa, pools, three restaurants, tiki bar, and more.

Book your stay at Cheeca Lodge & Spa here.

See more places to stay in Islamorada here.

Best Places to Stay on Marathon

Marathon is further south along the Florida Keys, just a one hour drive from Key West. This is a city spread across 13 islands.

Stay in Marathon for the famous Seven Mile Bridge, access to The Turtle Hospital, the bike or tram ride to Pigeon Key, and nearby Bahia Honda State Park.

Marathon has a reputation of being quiet and relaxing, with good fishing and diving.

WHAT WE DID | We stayed at Isla Bella Beach Resort in Marathon for one night, and all I can say is I wish I’d stayed here longer! What a stunning hotel, with impeccable service, stunning beaches, and delicious food. More details below.

Yacht Haven ($) | Marathon

Want to stay on a house boat in the Florida Keys? Yacht Haven is my pick for reasonably-priced, unique accommodation in Marathon.

This place is a “floating aqua lodge” and is made up of house boats in a marina! With prices around $150/night, this would be a very special, unique Florida Keys experience.

Book your stay at Yacht Haven here.

Isla Bella Beach Resort ($$ – $$$) | Marathon

Isla Bella Beach Resort is a luxury beach-side hotel and this is where we stayed. I HIGHLY recommend booking a stay here, if you can!

Every single room at Isla Bella has an ocean view, and there is 1-mile of waterfront.

Why did I love Isla Bella so much? From the champagne upon arrival and complimentary bikes, to the gracious staff and jaw-dropping bathroom, I found that Isla Bella was luxurious without any of the pretentiousness that frequently comes with that caliber of service.

Even if you’re not normally a “luxury” traveler, you may be surprised at their reasonable rates and I encourage you to check them out!

Book your stay at Isla Bella Beach Resort here.

See more places to stay in Marathon here.

Best Places to Stay on Big Pine Key

Big Pine Key is one of the least touristy areas along the Florida Keys and for that reason I had to include it in this guide.

Visit Big Pine Key for Grimal Grove (a unique tropical fruit farm) and the Key Deer Refuge. Stay overnight here if you want to relax and visit somewhere as “off the beaten path” as you can get in the Florida Keys.

WHAT WE DID | I discovered Big Pine Key and immediately knew I’d want to stay here on a return visit. The owner of Grimal Grove recommended Deer Run on the Atlantic (a sustainable bed and breakfast) to me – that is so my vibe, and would absolutely be my pick on a return trip to the Florida Keys.

Big Pine Key Motel ($) | Big Pine Key

Big Pine Key Motel is one of the best budget accommodations in all of the Florida Keys, with prices around $100/night.

Rooms are clean and cheerful, and the motel is only a 10-minute drive from Bahia Honda State Park.

Book your stay at Big Pine Key Motel here.

Deer Run on the Atlantic ($$$)

Deer Run on the Atlantic is a sustainable bed and breakfast that is 100% vegan. They are the highest rated property in terms of sustainability in the Florida Keys.

The price tag is hefty, at $475+/night with a three night minimum, but the setting is beautiful, directly on the beach on one of the quietest keys.

Book your stay at Deer Run on the Atlantic here.

See more places to stay in Big Pine Key here.

Best Places to Stay in Key West

Ahh, finally… Key West! This southernmost island needs no introduction, but here’s one anyway: come here for a tropical village filled with historical sites (Hemingway House, Truman Little White House, and Southernmost Point among them), bustling bars, sunset sailboat rides, mouthwatering key lime pie, and more.

Where to Stay in Key West: Old Town vs. New Town

In discussing the best places to stay in Key West, I have to mention that Key West is divided into “new town” and “old town” areas.

The new town (sometimes called downtown) has grocery stores, drugstores, and some hotels. However, it’s not very walkable and not geared toward tourists.

The old town is what you think of when you think “Key West.” It’s pedestrian-friendly, filled with pastel cottages, bars and restaurants, and most everything you’d plan to visit.

As such, I’m only sharing accommodation options in the old town area of Key West. Below are the best places to stay in Key West for all budgets.

WHAT WE DID | We stayed at The Gardens Hotel in Key West for two nights and I highly recommend it. It’s a perfect oasis in the chaos of Key West, complete with a pool, breakfast, wine bar, and free parking! More about it below.

Southwinds Motel ($) | Key West

Southwinds Motel is one of, if not the, most affordable accommodation in the old town area of Key West. The motel has two private pools and is only 2-minute walk from Duval Street.

With an 8.1 rating on Booking, it’s the best of both world in terms of value for money in Key West.

Book your stay at Southwinds Motel here.

The Gardens Hotel ($$ – $$$) | Key West

The Gardens Hotel is my top pick for the best place to stay in Key West. This is where we stayed and it was truly idyllic.

Boutique rooms are set across two historic, old houses, with a beautiful garden courtyard in the middle where guests have breakfast each morning. The hotel also has free parking (a WIN in Key West), a wine bar, and… a resident tortoise!

The location is perfect, in a quiet area that’s still walking distance from everything. This is a particularly great pick for couples.

Book your stay at The Gardens Hotel here.

The Mansion on the Sea ($$$) | Key West

The Mansion on the Sea – Southernmost House is not only one of the most famous places to stay in the Florida Keys, but also one of very few oceanfront hotels in Key West.

This luxury accommodation is set in a historic mansion built in 1897. In addition to the coveted Key West beach access, guests also have a private pool, complimentary breakfast, parking, and more.

Book your stay at The Mansion on the Sea here.

See more places to stay in Key West here.

How Many Keys Should You Stay on in the Florida Keys?

A tricky part of itinerary planning in the Florida Keys is choosing not only which, but how many islands to stay on.

The answer is quite personal, and depends on the total amount of time you have in the keys, as well as travel preferences (such as the activities you like doing, and how often you like changing accommodations).

Across our week-long Florida Keys road trip, we stayed in three different hotels on three different keys. This was as fast-paced as I personally would want to do it.

You could easily do a two-week road trip and still only stay at three accommodations, and just spend longer exploring each key and its surrounds.

Keep in mind that the drive from Miami to Key West is only about 3.5 hours total, meaning that as long as you have a car you can easily drive to explore other keys while basing yourself on one for multiple days.

Final Thoughts on the Best Places to Stay in the Florida Keys

I know it’s a lot of work to plan a trip to the Florida Keys. Not only do you have to familiarize yourself with the geography, including the best islands to stay on, but you also have to choose the best hotels for your travel style. With so many accommodation options in the Florida Keys, this can easily lead to decision fatigue!

I hope that my guide to the best places to stay in the Florida Keys is helpful to you as you plan your trip – and can reduce that overwhelming feeling just a little bit.

Please let me know in the comments if you found this article helpful, and anything I can do to keep it updated. Happy travels!