The Florida Keys are a great destination any time of year.
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If the weather isn’t good for a snorkeling adventure or lounging on the beach, there’s something else on the docket—from museums to national parks to lively nightlife. That being said, there is one catch when it comes to visiting the Keys…
There isn’t much space.
The Florida Keys are made up of over 1,700 islands, but only 43 are inhabited. In total, the Keys have around 137 square miles of land to work with. Spread across the archipelago, first-time visitors will notice there’s a bit of a learning curve.
While you figure out where to go, what to do, and how to get there, take a shortcut with this list of VRBOs and Airbnbs in the Florida Keys. I’ve dug deep into both platforms to find mid-range rentals in the Keys that deliver on some type of wow factor, from houseboats to bungalows close to Duval Street.
11 VRBOS and Airbnbs in the Florida Keys to keep an eye on
Treetops home in Key Largo
This stunning beach cottage gives you access to a private, sandy inlet that’s shared with two other rentals. You can kick back on a sun lounger or take one of the available kayaks or paddleboards for a spin on the water. This rental is a one-bedroom that sleeps up to four and comes with a large covered patio for lounging.
Bright cottage in Islamorada
Funky, bright, and still dozy, this cottage is located right on the water and comes with dockage ($25 per night). In fact, it’s a renovated fishing cottage from the 1940s. If you’ve been interested in visiting the famed Lorelai Restaurant & Cabana Bar, it’s within walking distance.
Lovely studio escape in Islamorada
If you prefer brighter, more modern stays, book this Islamorada oceanview studio instead. It puts you in a great spot to explore the island, and also gives you access to all the resort perks from Caloose Cove Resort and Marina. Plus, the couch is a pullout, letting you sleep three.
Luxury treehouse with boat parking in Tavernier
This gorgeous, hidden-away treehouse-style bungalow sleeps up to eight in four bedrooms. It’s swanky and stylish, ideal for large family or group trips where everyone is comfortable splurging a bit. In exchange, you get a high-design and comfortable stay with tons of private land that’s laden with tropical plants.
Conch Key cottage
This two-bedroom cottage, a classic that dates back to the 1950s, comes with ramp access. You’ll be in the heart of a historic fishing village, and you can still go pick out your catch that you want for dinner that night. If you want a quaint, charming stay in the Keys, Conch Key is hard to beat.
Beachfront 3-bedroom in Layton
Located on a property that comes with cleaning services and a large, shared pool, this three-bedroom rental gives you the best of both worlds. On one hand, you have the keys and Long Key State Park within walking distance. On the other hand, you can hole up and enjoy the property’s sand canal views and private pool for endless days in the sun.
Turtle-by-the-Sea guest suite in Key Colony Beach
This guest suite is a perfect romantic getaway. You’ve got total privacy in a tiny-home-style setup, which is well-appointed and decorated for its size. The rear opens onto a dock overlooking the water, immersing you in nature and giving you a perfect paddleboarding/kayaking setup.
Floating houseboat rental in Big Pine Key
Who wouldn’t want to stay on a houseboat in the Keys? (I’ve got one more recommendation below.) This ‘aqualodge’ sleeps up to four thanks to a pullout couch. It’s located on Big Pine Key’s quiet and cozy Florida Keys Resort and Marina, meaning you also get some resort perks with your stay.
Home with private pool and dock in Marathon
This grand two-bedroom stay sleeps up to six and comes with a private, heated pool. Just feet away from the pool is a private dock, making this great for anyone who wants to get out on the water during their stay. It’s also located near the action in Marathon, letting you choose between quiet pool days and afternoon bar crawls.
Cozy houseboat in Key West
This houseboat gives you pure old-school Key West vibes, with a few extra perks. You can float on the water without a care in the world, with Duval Street only 15 minutes away. With a full kitchen and bath, you’ve got everything you need—plus extras like blackout shades and extra-comfy bedding.
Kate’s Krawl 1-bedroom near Duval St in Key West
If you want a more Duval-forward (Duval Street is where all the partying and fun happens in Key West) rental, check out this one-bedroom rental that sleeps up to four. You’ve got a full backyard to hang out in, along with a renovated home that is decked out in modern beachy décor.
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