The most southerly point of the United States, Florida Keys could be another country. One hundred islands made up of sandbars and mangroves welcome gently lapping turquoise waves onto their white sands. The flat, calm waters mean it’s the perfect place to go stand up paddle boarding or kayaking for lazy days hopping between the islands!

After a day of paddling or swimming, you’ll need somewhere to come back to. Why not take a look at vacation rentals in the Florida Keys? These can be anything from your own apartment in a condo to a yacht. They’re the perfect way to get a local feel for this stunning part of the world.

With that in mind, we’ve put together this list of the best Airbnbs in Florida Keys, curated by travel style, budget, and location. There are also some awesome Airbnb Experiences, so you can have a blast when you’re there. Let’s check it out!

Key West, Florida

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Quick Answer: These are the Top 5 Airbnbs in Florida Keys

Bella Vita Condo steps from Duval Florida Key

Bella Vita Condo steps from Duval

  • > $$
  • > 2 Guests
  • > Wrap-around porch with chairs
  • > Self-check-in
Unique Camping Shed near beach Florida Key

Unique Camping Shed near beach

  • > $
  • > 2 Guests
  • > King bed
  • > Kayak campfire stargazing evenings
Multi-Million Beach Mansion with pool Florida Key

Multi-Million Beach Mansion with pool

  • > $$$$$$$$$$$$$
  • > 10 Guests
  • > Private beach
  • > Oceanfront heated pool
Key West Cozy Home Florida Key

Key West Cozy Home

  • > $
  • > 1 Guest
  • > Awesome location
  • > Kayaks and paddle boards for rent
Mallory House Room Florida Key

Mallory House Room

  • > $
  • > 2 Guests
  • > Dedicated workspace
  • > Close to cafes and restaurants

What to Expect from Airbnbs in Florida Keys

From one of the best US National Parks, the Everglades to Key West, the most southwesterly point, it’s more than two hours by car (about 100 miles). So, location is important here.

With your own transport (maybe even get an RV rental?), the Keys are pretty easy to navigate, so it’s not the end of the world if you’re a little journey from your desired destination.

The next thing to take into consideration is cost. Florida Keys isn’t cheap; however, because Airbnbs offer great value for money, you can be assured that every dollar you spend goes towards a high-quality vacation rental, whether that’s a classy condo, a quirky tiny house, or a luxury yacht.

Many vacation rentals in Florida Keys are professionally managed through companies. However, you will find a few properties where you’ll be welcomed by a local host.

plane flying over florida keys

Florida Keys is a narrow strip of land surrounded by the sea. Since you’re never more than a few minutes from the water, why not stay on a boat? A boat could be anything from a small vintage sailboat to an ultra-luxurious mega yacht.

If you’re planning a group celebration, a villa is a great option. These large properties often have multiple bedrooms and living spaces indoor and out, so they’re ideal for families.

Condos (or condominiums) are like apartments, but a little different. If you’re from the United States, they’ll need no further explaining. You may even live in one! However, for travellers from the rest of the world, they’re a large building where you own or rent the living area of your building but share common areas.

The Top 15 Airbnbs in Florida Keys

Now you know what to expect and why you should choose vacation rentals, let’s get to the part you’ve all been waiting for. Here are 15 of the coolest Airbnbs in Florida Keys. You’re going to love them!

Bella Vita Condo steps from Duval | Overall Best Value Airbnb in Florida Keys

Bella Vita Condo steps from Duval Florida Key

Ideal for couples, this colourful property is a great value Airbnb in Key West. It’s less than half a block from Duval Street, and many other landmarks are within a stone’s throw. Back in the flat, you’ll be treated to bright decor, a king bed, flat-screen smart TVs, and a cosy living area. Enjoy your morning coffee on the porch and watch the world go by!

This spot has one of the best locations in Florida Keys – just half a block from Duval Street! The king bed makes it perfect for couples, who can spend the morning enjoying a coffee and people-watching from the porch.

Unique Camping Shed near beach | Best Budget Airbnb in Florida Keys

Unique Camping Shed near beach Florida Key

The Florida Keys are a lot of things, but cheap isn’t one of them. However, with some research, you can find affordable properties, such as this tiny house in Key Largo. Offering a glamping experience, there’s a king bed in the hut and a small outdoor space. Your host offers kayak campfire stargazing experiences too, so get in touch with them if you’d like to know more.

Is This the Best Backpack EVER???
audy on top of a mountain in japan with the osprey aether

We’ve tested countless backpacks over the years, but there’s one that has always been the best and remains the best buy for adventurers: the broke backpacker-approved Osprey Aether and Ariel series.

Want more deetz on why these packs are so damn perfect? Then read our comprehensive review for the inside scoop!

View on Osprey View on REI

Multi-Million Beach Mansion with pool | Over the Top Luxury Airbnb in Florida Keys

Multi-Million Beach Mansion with pool Florida Key

This place is just insane. You have your own private beach overlooking Summerland Key! Not only that, there’s a heated pool right by the ocean, a pool table, and a hammock. This place is perfectly set up for you to chill out and escape the real world. There’s space for up to ten guests, so it’s good for families and friends. We’re sure you’ll spend all your time outside, but it’s good to know there’s a 56-inch curved TV waiting for you in the living room.

Key West Cozy Home | Perfect Airbnb for Solo Travellers

Key West Cozy Home Florida Key

Home stays are a great option for solo travellers. They not only allow you to save some cash, but also to have a completely local experience during your stay. At this family home on Stock Island (near Key West), there are kayaks and paddleboards for rent, and you’re welcome to use the communal areas of the house. Did we mention the home is right on the water?!

Mallory House Room | Perfect Airbnb for Digital Nomads

Mallory House Room Florida Key

Being a digital nomad is becoming more and more common. All you need is a laptop, somewhere to work, and fast Wi-Fi. If you supply the laptop, Mallory House will give you the other two ingredients. This boutique hotel is close to the cafes of Key West, so if you fancy a change of scenery for the day, it’s easy to get one. When you’re chilling at the guest house, be sure to take your hosts up on their offer of a complimentary coffee overlooking Duval Street.

Travel with peace of mind. Travel WITH a security belt.
Active Roots Security Belt

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Hide Yo’ Money!

More Epic Airbnbs in Florida Keys

Here are a few more of my favorite Airbnbs in Florida Keys!

Romantic Retreat with private deck | Best Short Term Rental for Couples

Romantic Retreat with private deck Florida Key

This cute, free-standing cottage dates back to the 1800s and is the perfect romantic Airbnb for a couple. Not only does it have a king bed inside, but there’s a rocking love seat on the private deck as well as a table and chairs – and a private hot tub! There are also heated swimming pools on the property that you’re welcome to use.

Tropical family-friendly home | Best Airbnb in Florida Keys for Families

Tropical family-friendly home Florida Key

Another property close to Duval Street in Key West, this Airbnb is perfect for families. There’s room for up to eight guests across three bedrooms, with singles and sofas in the smaller room perfect for children. With a fully equipped kitchen, you can save a few dollars over eating out, and there’s free parking on the driveway, too. You can even bring your furry friend as pets are welcome!

Floating Tiny House – 70’s sailboat | Best Boat in Florida Keys

Floating Tiny House – 70’s sailboat Florida Key

This renovated 25-foot sailboat hails from 1978 and is packed with retro charm. It’s docked in Stock Island marina, so as well as your cute boat, you’ve got access to the Perry Hotel. Here, there’s a bar, gym, restaurants, pools, and even dog parks! The boat, named Poppy, is quite small. It’s ideally suited to a solo traveller, or it could be a romantic retreat for a couple.

Four bedroom villa on Duck Key | Best Villa in Florida Keys

Four bedroom villa on Duck Key Florida Key

Duck Key is about halfway down Florida Keys, and there are some pretty awesome villas here – such as this one. Another property ideal for families, four bedrooms can sleep up to ten guests, there’s a fully equipped kitchen and a swimming pool. As well as free parking, you can take advantage of a 35-foot dock to moor a boat.

Affordable Beachfront Luxury sleeps six | Best Condo in Florida Keys

Affordable Beachfront Luxury sleeps six Florida key

Back in Key West, you’ll find this cool condo close to Smather’s Beach. The large indoor space boasts a kitchen, sitting area, and three bedrooms, but it’s the shared spaces that make this place special. You’ve got access to an Olympic sized swimming pool and hot tub right by the beach! Prefer to stay dry? Make use of the grilling area and covered picnic areas and enjoy some lunch. Go on, treat yourself!

Stars and Stripes Lifeguard Tower | Most Unique Airbnb in Florida Keys

Stars and Stripes Lifeguard Tower Florida Key

Always dreamed of appearing in Baywatch? That may never happen, but you can pretend when you’re staying in this lifeguard tower! Located at the very north of the Keys in Key Largo, it offers easy access to the Everglades too. Breakfast is included in this no-frills accommodation, and it’s sure to make memories that last far beyond your flight (or drive) home.

Casa Loca | Best Airbnb in Key West

Casa Loca Florida Key

A lot of the Airbnbs we’ve seen so far are in Key West, and that’s no surprise; it’s the most popular location in the Keys! It’s probably got the biggest selection of accommodation, but here’s one more we think you’ll love. Boasting a private heated pool and concierge service, this luxurious retreat is ideal for a family or group of friends. It’s usually booked, so move fast!

Two bedroom condo for four | Best Airbnb in Islamorada

Two bedroom condo for four Florida Key

Islamorada and Tavernier are closer to the north end of the Keys, and they’re much quieter than Key West. For some, that might be a big attraction. This condo has room for four guests across two rooms, so it could suit a small group or a couple. You have access to a cafe, a large heated pool, and spectacular ocean views from here.

Charming Key Largo Cottage | Best Airbnb in Key Largo

Charming Key Largo Cottage FLorida Key

Another Key Largo Airbnb, this cute cottage is right on the water and comes with kayaks and paddleboards. The tiny house cleverly uses space to make room for up to four guests in a studio style room in an RV park. The cottage has a fully equipped kitchen stocked with a coffee maker and other useful appliances.

Fully furnished efficiency studio | Best Airbnb in Marathon

Fully furnished efficiency studio Florida Key

Last but not least is this small cottage by the ocean in Marathon. It’s great for solo travellers or couples on a budget. The studio-style apartment comes with a fully equipped kitchen, queen bed, and an open plan living space. Outside, you can chill out at the picnic table and enjoy a meal under the stars in the evening!

What To Pack For Florida Keys

Pants, socks, underwear, soap?! Take it from me, packing for an Airbnb stay is not always quite as straightforward as it seems. Working out what to bring and what to leave at home is an art I have perfected over many years.

Don’t Let Snorers Keep You Awake!
Don’t Let Snorers Keep You Awake!

Ear Plugs

Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.

Keep your laundry organized and stink free
Keep your laundry organized and stink free

Hanging Laundry Bag

Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

Stay Dry With a Micro Towel
Stay Dry With a Micro Towel

Sea To Summit Micro Towel

Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

Make Some New Buddies…
Make Some New Buddies…

Monopoly Deal

Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

Reduce Plastic – Bring a Water Bottle!
Reduce Plastic – Bring a Water Bottle!

Grayl Geopress Water Bottle

Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!

Don’t Forget Your Florida Keys Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Final Thoughts on Florida Keys Airbnbs

So, there you have it. Those are the 15 best Airbnbs in Florida Keys, with some really cool Airbnb Experiences thrown in too. Whether you want to stay in a tropical villa with a pool, a cool condo, or even a tiny house lifeguard tower, there’s an Airbnb in Florida Keys for you.

Still can’t make your mind up? Well, let us round off with reminding you of our overall best value Airbnb in Florida Keys. That’s the Bella Vita Condo steps from Duval. Located just steps from the Key West Historic District, it has awesome reviews, and you’re sure to love it.

We hope that wherever you choose to stay in Florida Keys, you have a fantastic vacation. To keep yourself and your belongings safe, make sure you check out World Nomads for travel insurance!

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