The coolest Airbnbs in Florida for a totally unique trip

Best for: families

Bayfront Coconut Grove is Miami’s most historic neighborhood, filled with lush tree canopies, historic bungalows and a bohemian vibe. Don’t be surprised to spot peacocks strutting in the wild down quiet residential streets and pale pink ibises perched in banyan trees, lending the whole area a magical, jungle-like atmosphere. This two-bedroom Grove bungalow is the perfect perch to soak in all of the charms of this somewhat less-traveled Miami neighborhood. The newly renovated pretty-in-pink, tropical modern bungalow is outfitted with a shady backyard on a picturesque street that’s ideally located within a few blocks of the area’s main shopping, dining and entertainment district and also Biscayne Bay where sailboats dot the horizon. The home is bright and airy with a modern kitchen, bathroom and furnishings for a stay that’s both comfortable and stylish with plenty of character. There’s also an outdoor grill, table and cozy patio furniture for entertaining under the moonlight or whiling away an afternoon with a good book in the shade.

Time Out tip: If you’re travelling with children or a dog, there’s both a playground and a dog park just opposite

Rooms: Two bedrooms. Sleeps four guests

Location: Coconut Grove, Miami

Price: From $500 per night

Why would a local recommend it? 'There’s something so romantic about Coconut Grove, its lush tree canopy and historic streets, plus the area’s dining scene is only getting hotter.'

Best for: luxury stay

Situated within the oceanfront, eco-lux 1 Hotel on South Beach’s northern edge, this Airbnb grants travelers all the amenities of a luxury resort with the comforts of residential condo living. The updated one-bedroom unit can sleep four with a king-sized bed in the bedroom and a foldout sofa in the living room. With modern furnishings and décor in a white-washed color palette, it exudes quintessential South Beach style. A full kitchen is decked out with modern appliances, including a dishwasher and Nespresso machine, while the enormous bathroom provides a spa-like experience in sand-toned marble tile. There’s also an in-unit washer-dryer. But perhaps best of all, the oversized oceanfront balcony provides dazzling views of the poolscape, South Beach’s Art Deco skyline, and, of course, the turquoise ocean. Guests enjoy access to all of the resort’s amenities, including four pools (including a rooftop pool with a trendy bar), multiple restaurants, and a spa, all in a prime South Beach location.

Time Out tip: You’re a stone’s throw away from the famous Lincoln Road Mall, a buzzing hub of restaurants, boutiques, art shops, and a cinema

Rooms: One bedroom. Sleeps four guests

Location: Miami Beach, Miami

Price: From $1,150 per night

Best for: solo travellers

Shipping containers are often associated with hipster hangouts in cities, but the Caja Verde could not be further from its urban beginnings. Set in the woods of Gainesville, inside this well-designed rental you’ll find old school furniture including wooden floors and a four-poster bed. Outside, this Airbnb is a great opportunity to see some native wildlife. You might see possum, raccoons and armadillos, a ‘medium-sized alligator’ in the back pond (this is Florida after all) and the very occasional black bear which was once spotted in the swimming pool.

Time Out tip: Mosquitos can be intense in August and September so bring bug spray

Rooms: One bedroom. Sleeps two guests

Location: Kirkwood, Gainesville

Price: From $125 per night

Best for: big groups

If you’re the kind of person who gets bored easily this is the Airbnb for you. Feel like bowling? There’s a private two-lane alley with neon pins. Want to expend some energy? Have a go on the indoor basketball machine or splash about in the indoor swimming pool with a huge TV. Want to be entertained? Snuggle up in the 14-seat cinema. There’s a strong sports theme throughout the place, each of the 12 king bedrooms is decorated after a different kind of game and the open-plan kitchen has some inventive basketball net lights. It’s a big space, perfect for families and is in the sought-after Kissimmee neighbourhood of Orlando. To know that Florida's Airbnbs really do have it all, this is all the proof you need...

Time Out tip: If all the fun and games inside this Airbnb isn’t enough for you, Disney World is about a 10-minute drive away

Rooms: 14 bedrooms. Sleeps up to 40 guests

Location: Kissimmee

Price: From $1,111 per night

Best for: animal lovers

If you’re looking for something a little different, why not try pitching up in an actual barn? Yep, really. This private barn studio on Florida farm is surrounded by grazing donkeys and horses (named Daisy, Sundance, and Jazzy), so you can actually connect with nature. There’s a fire pit, hammock, swing chair, and lake outside, as well as some fantastic walking trails to discover. The farmhouse can sleep four, so it’s perfect for families.

Time Out tip: You can book horse riding sessions through the host

Rooms: One bedroom. Sleeps up to four guests

Location: Vero Beach

Price: From $176 per night

Best for: low-cost stays

If you’re seeking serious off-line time, consider this beautiful Amish-built log cabin in the Fort White woods. Yes, you’re only minutes away from Ginnie, Ichetucknee, Poe and Blue Springs Gilchrist, but there’s also the pull of keeping yourself tucked up nice and snug in the woods with only you, your beau and a book for company. Build a fire in the fire pit, go canoeing on the river, hike through the landscape and spend time getting to know the local deer population. Stress? What stress?

Time Out tip: The cabin comes with free firewood, which can use in the park’s fire pit and BBQ

Rooms: One bedroom. Sleeps four guests

Location: Three River Estates, Fort White

Price: From $135 per night

Best for: parties

It’s the garden that really steals the show at this design-led bungalow in the west-coast destination of Naples. Among the manicured lawns and palm trees, you;ll find a retro, 50’s style pool decorated with geometric tiles and dotted with sun loungers – it’s covered with a stunning glass roof for swimming in all weathers – as well as a huge gazebo strung with lights and billowing curtains for up-scale alfresco dining. Inside the rooms are clean and bright with exposed beams and beachy rattan furnishings; fitting because the Vanderbilt beach area is just 15 minutes away. 

Time Out tip: You’re just 15 minutes away from the Vanderbilt beach area and Mercato shops and restaurants

Rooms: Three bedrooms. Sleeps eight guests

Location: Naples

Price: From $504 per night 

Best for: off-grid stays

Some places just look far too sophisticated to deserve the name ‘treehouse’. This is one of them. Banish any ideas of rustic edging because the only ‘getting back to basics’ you’ll be doing here is re-connecting with a sense of pure peace. The wooden walls glow almost golden and there’s a confidence underpinning a collection of design choices which are all steer towards the elegantly understated. We love those super-comfy chairs in the living room which can either point forwards towards to television or – our preference – swivel round to face the surrounding trees. Make yourself a hot drink and soak up that scenery.

Time Out tip: If you’re brave enough to go crock hunting, put on your hiking boots and walk the Egan’s Creek Greenway Trail

Rooms: One bedroom. Sleeps two guests

Location: Fernandina Beach, Amelia Island

Price: From $248 per night

Best for: being close to the beach

After a top-notch beachside vacay? If so, you need to give this place some consideration. Not only is the entire place beach-themed (we’re talking shell lamps, anchor-shaped wall hangings, the lot) but the sand itself is literally steps away from the front door. The chilled-out town of Gulfport is right there, too – it's a low-key cracker of a city full of great food and hosting a vibrant art scene. If you’re looking for lazy beach days, this is just the ticket. St Petersburg (Florida) is just five miles away, too.  

Time Out tip: There’s a farmers market every Tuesday from 8am to 2pm

Rooms: One bedroom. Sleeps two guests

Location: Gulfport

Price: From $378 per night

Best for: adventure seekers

We know, we know. It kind of looks like what a wooly mammoth might look like if someone turned it into an Airbnb. Sure. But take a closer look and this Airbnb in Key West is spectacular. Wake up every morning to the sea outside under a tiny sloping roof on the Key West waters before hanging out on the hammock all day, reading, having a beer, or just taking it all in. What could be better?

Time Out tip: The tiki is only accessible by boat. The local marine services, Ship 2 Shore, operate a shuttle

Rooms: One bedroom. Sleeps two guests

Location: Pearl Basin, Kay West

Price: From $763 per night

Best for: visiting Disney World

There’s nothing Goofy about this Mickey-Mouse-themed condo. The whole place is dedicated to Disney’s original fan favorite, with everything from bedsheets to bathmats styled after the legendary mouse. What’s more, you can drive from the condo to The Most Magical Place on Earth in under five minutes and be first on the rides – hassle-free. The space itself sleeps four, so there's room for all the family. 

Time Out tip: You’ll also have access to the resort’s outdoor pool

Rooms: One bedroom. Sleeps four guests

Location: Kissimmee

Price: From $155 per night

Best for: exploring the Everglades

Perched alongside the water, this perfectly proportioned home offers lovely views of the nearby mangrove trees. It’s got ample parking space for four vehicles, plus a trailer, and is a great choice for guests planning on spending a lot of time in the Floridian great outdoors (including the nearby Everglades National Park). Enjoy your breakfast with treetop views and make use of the deck area when you want to have a conversation with just yourself, the water and the sky. 

Time Out tip: June is off season and so the town gets sleepier, with many restaurants closed until autumn

Rooms: Two bedrooms. Sleeps six guests

Location: Ochopee, Everglades City

Price: From $440 per night

Best for: rooftop sundowners

We took a shine to this place the moment we laid eyes on it. A brand-new apartment with a heated plunge pool, outdoor shower, large patio (with bar, natch) and a share rooftop deck with hammocks and fabulous sea vistas, this home will leave you wanting for very little. There’s also the option of a barrel sauna and cold plunge pool for a small extra cost each day. Inside, it’s got a lovely feminine, hand-crafted aesthetic with many individualistic touches to make it feel like a real home. We think the kitchen, with its mint green fridge is particularly cute.

Time Out tip: A barrel sauna and cold plunge is available for unlimited access at an additional $20 per day

Rooms: One bedroom. Sleeps four guests

Location: Cocoa Beach

Price: From $251 per night

Best for: group trip to Disney World

For a spot of luxury, grab this eight-bed in Encore Resort, located right next to Disneyland – that’s if you can ever drag yourself away from its insane outdoor pool surrounded by sun loungers and hammocks to chill in. The inside is even more lavish, with a huge dining table and living area, complete with a flat-screen TV. If you run out of things to do, there’s a grill and basketball hoop, too. 

Time Out tip: Its 15 minutes away from Disney World and 20 minutes from Universal Studios

Rooms: Eight bedrooms. Sleeps 16+ guests

Location: Four Corners, Kissimmee

Price: From $631 per night

Best for: family adventures

Do you remember Taylor Swift’s cottagcore lockdown album ‘folklore’? That’s basically the whole vibe of this three-bed log cabin in beautiful Suwannee County. A brilliant Airbnb for a family or larger group, this wood-on-wood-on-wood (it’s all made from wood) home will have you disappearing into a land of chunky knitwear, muddy boots and fireside whiskey in no time. Make the most of the backyard grill as evening turns into nighttime.

Time Out tip: Feeling daring? Try the alligator bites at Roy's Restaurant in Steinhatchee

Rooms: Three bedrooms. Sleeps nine guests

Location: Live Oak, Suwannee County

Price: From $770 per night

Best for: glamping vibes

A tiny but perfectly formed home in Ocala, this lovingly maintained A-Frame gives a slightly slower and more peaceful view of Floridian life. Chicly outfitted internally, the rooms immerse guests in the glossy surrounds of wood panelling and black beams. It’s super cosy and – most importantly – a cooling spot for a hot day. But really, this home is all about the outdoors which in effect act as an additional ‘room’ (or ‘rooms’). There’s a hot tub and a firepit, plus just plenty of outdoor dining and seating space for either sharing with friends or just spending along time in with a book.

Time Out tip: Equestrian fan? Head to Gypsy Gold Horse Farm for a guided tour around this beautiful place

Rooms: Two bedrooms. Sleeps five guests

Location: Ocala

Price: From $499 per night

Best for: hiking trails

Looking for something a little less in the thick of it and a little more submerged in nature? This is the place. This log cabin on the river in Brooksville, Florida is right in the middle of the woods and is surrounded by a bunch of biking and hiking trails and kayaks on the riverfront. Inside is utterly luxurious, with a Scandi-style design and a cozy living area, along with a bedroom that can only be accessed via the little staircase. If you want to escape, try this. 

Time Out tip: Papa Joe's Italian restaurant in Brooksville does the best pizzas

Rooms: One bedroom. Sleeps four guests

Location: Brooksville

Price: From $383 per night

Best for: sunset views

Get a slightly different Floridian vibe with a stay at this marshland utopia. Located just three miles from Downtown St Augustine, this gem of a property feels both understatedly chic and high-class luxury. Originally built in the 1930s, it’s been given a thorough makeover by its hosts so that inside you’ll find lush velvet bedspreads, chic mid-century modern furniture and rustic woodwork given a high-shine finish. But the main draw? Those views, baby. Those views.

Time Out tip: You can fish from the dock

Rooms: Two bedrooms. Sleeps four guests

Location: Vilano Beach, St Augustine

Price: From $612 per night

Best for: sea lovers

This Airbnb takes riverside accommodation quite literally. Sleeping up to three people, this Hunter 26 sailboat is anchored in Key Biscayne Bay, so you’ll be treated to gorgeous views of Miami. When you want to visit dry land, your skipper will take you to the famous Coconut Grove area via a dinghy. Inside the boat, you have nautical and luxury interiors, and kayaks. If you want to step somewhere a little busier, you're also anchored pretty close to Miami. Not sure why you would though – the sunsets are epic here.

Time Out tip: The last ride to the boat is 9pm so keep this in mind when planning your days and nights out. 

Rooms: One bedroom. Sleeps two guests

Location: Biscayne Bay, Miami

Price: From $147 per night

Best for: couple’s holiday

Sleeping up to two guests, this Panama Beach-based condo is ideal for water lovers. Not only do you get access to the warm waters of the Gulf of Mexico but you can also splash around in the oceanfront waterfall swimming pool, three hot tubs, and an additional heated pool – H2-Woah! When you're on dry land, this beautiful spot has a gorgeous deck overlooking the sea you've been having fun in all day, and is a relative stone's throw from Panama City. 

Time Out tip: Try the daiquiris at Pineapple Willy’s restaurant

Rooms: One bedroom. Sleeps two guests

Location: Panama City Beach

Price: From $200 per night