I know, I know—the concept of cool is highly subjective.
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What one traveler adores, another is likely to complain about, especially when it comes to private rentals. Some prefer self-check-in while others want a little ‘hi, how are you’ from the host. Some travelers want ultra-fast wi-fi while others might prefer limited electronics on the property.
The list goes on and on when it comes to what makes a rental cool.
But I like to think that everyone is pretty open-minded and ready to go with the flow when they visit the Sunshine State. Florida is America’s preferred vacation spot for many valid reasons, from its affordable prices to all that great weather to its family-friendly, relaxed approach to life.
And there are many surprisingly cool Airbnbs in Florida that deliver on unique angles, from constructions like tree houses and repurposed Chinooks to farm stays and houseboats on the Atlantic.
Ready to count down some of the most unforgettably cool Airbnbs in Florida?
Cool Airbnbs in Florida for any type of adventure
Lakefront rental with an inlaid hot tub: Tiny home in Dade County
Who knew container homes could be so chic? This tiny but mighty rental is nestled on a small lake, letting you spot Sandhill cranes and other unique wildlife. The interior is warm and minimalist, while floor-to-ceiling windows let you feel immersed in the outdoors. The cherry on top is its inlaid hot tub, making this perfect for couples.
Stay inside a converted Chinook: Tiny home in Brooksville
This Chinook CH-47D tiny home gives you the chance to stay inside a repurposed tiny home. It comes with all the creature comforts you could want, from a full kitchen to an AC split unit. The Chinook has been mindfully updated to highlight its mechanical features, too, letting airplane nerds fully geek out.
Full access to water activities: Waterfront Sanctuary on Black Creek
This two-bedroom home sleeps a total of five guests, letting you bring some company as you enjoy the wonders of Black Creek. There’s a small, sandy beach, a massive deck that’s tiki-themed, an outdoor grill area, and an outdoor hot tub, along with paddle boards, kayaks, and even a blow-up water slide for kiddos. You won’t care that you’re not at a beach—you’ll be too busy splashing around having fun.
Luxury mini-stay with a private hot tub: Tiny home in Bradenton
Who says cool Airbnbs in Florida can’t be intimate and romantic? This tiny home stay near Anna Maria includes a newly built tiny home with a chic décor and plenty of outdoor space for you to lounge amidst the greenery. There’s also a hot tub for you and your lover to enjoy. Just know that there’s a 10 pm noise ordinance in this zone, meaning you’ll need to zip it when the hour hits. If you’re anything like me, you view that as a perk.
Jungle-themed rental with soaking tubs: Tiny home in St. Augustine
Along with the tiny home listed above, this is my second pick for romantic but cool Airbnbs in Florida—and it’s heavy on the jungle theme. The tiny home is hidden amid lush, tropical gardens, which also hide two large soaking tubs. There’s also a sauna and fire pit, if you’re on the hunt for spa features, too. It looks like hosts are also willing to do a little zhuzhing up if you’re visiting for a special occasion.
Treehouse with a wraparound porch: Treehouse in Saint Cloud
This teeny-tiny treehouse is beautifully made, with large branches crossing right outside the windows. You’ll truly feel elevated, which is great because the tiny home has floor-to-ceiling windows that let you take advantage of the view. There’s even a gorgeous skylight. As a travel writer who covers a lot of so-called treehouse rentals, I rarely see projects this polished.
Fairytale-style glamping: Serenity Acres Glamping Retreat in Arcadia
Similar to treehouses (above), I see quite a few glamping-style properties listed on Airbnb during my research. Most aren’t ‘true’ glamping grounds, meaning they tend to skimp on luxury and/or functionality. At Serenity Acres, you can count on both luxury and functionality.
Their large bell tent includes a king-sized bed, temperature controls, and includes full bathroom and kitchenette facilities nearby. There are other perks, too, including a fire pit and—my favorite—privacy. There’s only one glamping tent on the ground, meaning you get the full site to yourself.
Converted bus turned tropical oasis: Skoolie in the Trees at Vero Beach
If the repurposed Chinook doesn’t do it for you, maybe this converted bus will. The rental is inside an old-school ‘skoolie’ bus, parked and renovated under lush tree coverage. Though the shower is located outside, the interior is fully decked out—including a stove and private bedroom.
Houseboat stay: Modern Houseboat on the water in Stuart
If you love the water, you’ll love this upscale houseboat stay. Its massive windows let you enjoy harbor views, while the location also puts you within walking distance to historic, downtown Stuart. Sunset Bay Marina & Anchor also has its own on-site restaurant and coffee shop. The rental also includes two free bike rentals.
Geodome in the forest: Glamping Geodome in High Springs
Most travelers who visit Florida are focused on its beaches—but don’t forget that Florida is also home to crystal-clear springs. This glamping Geodome puts you only minutes from some of the state’s loveliest springs. The Geodome is also impressive on its own. It’s warmly outfitted for a cozy stay, includes a kitchenette, and has plenty of clear paneling to let you enjoy the forested view. Just know that you need to leave to use an outdoor toilet.
Perfect for horse-lovers: Horse Barn Retreat in Zephyrhills
If the prospect of staying on a horse farm and getting up close to equine creatures is high on your bucket list, look no further. This stay isn’t just on the grounds of a farm with horses—the Airbnb is actually inside the horse barn. There’s a small and beautifully appointed suite, with a bathroom next door (you need to walk out to get to it). The farm has horses, ducks, chickens, cats, bunnies, and more.
Treehouse-style retreat: Hidden Oak Hideaway in Arcadia
This bohemian treehouse-style escape gives you the perfect chance to disappear in the forest. The property oozes charm, from its cozy loft to its outdoor lounge. There is a range of packages you can book, too, from a couples massage to a movie night that involves staff bringing out a projector for you to watch videos in the forest. Very cool! Just know that you’ll be using an eco-toilet and that the bathroom is outdoors.
