20 Coolest Airbnb Rentals in Florida (2024)

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The Yurt at Danville - Geneva

If staying overnight in a tent seems appealing to you, then you might consider choosing a yurt as your next holiday rental. Located on a private airstrip adjacent to Lake Harney and part of the St. Johns River, the Yurt at Danville offers a luxury glamping experience. You’ve got plenty of space here, as the 14-foot vaulted ceiling and 5-foot skylight provides the comforts of home, while the air-conditioning, full bath, mini kitchen and king size beds are just icing on the cake. Take your loved one for a romantic getaway, where you can share a bottle of wine on your large porch, start up the barbecue, and stargaze through the skylight in the dome of the yurt.

Ocean Front Private Getaway - St. Augustine

Located in St. Augustine, this adorably charming pink-hued Airbnb has got everything you need for a memorable beach getaway and qualifies as one the coolest Airbnbs in Florida. Accommodating up to 13 guests in its four-bedroom layout, the three-story A-frame home is bright and cheery with a beautiful interior and private beach access. Soak up the sunshine on the deck, sit around the fire pit, or head to the beach for a beachside stroll. Best of all, you’re only 5-10 minutes from the downtown St. Augustine area and its famous historic attractions.

Relaxing Jungle Bungalow Treehouse - Hernando

Two guests can stay at this jungle bungalow, which is set down a hidden pathway in the Florida wilderness. It features two platforms with plenty of convenient glamping amenities, including an outdoor shower, composting toilet, Black Stone griddle, gas stovetop, fridge, and air-conditioner. There’s plenty of outdoor space to hang out, and there’s even a smokeless fire pit where you can enjoy starry nights.

ManCave Apartment - Geneva

A manman caveace that you can only dream of, this ManCave Apartment in Geneva is a part of an active airplane hangar on a private airstrip in East Seminole County. Decorated with an eclectic collection of unique artifacts, you’ll find every nook and cranny covered with unique items. Providing a fun ambiance with a bar, satellite TV, and wood-burning fireplace, it is the perfect place to relax and unwind with a couple of your friends. You’ll have all the amenities you need for a weekend of fun, and if the weather is ideal, you might even see some of your neighbors flying their aircraft off the grass strip. The rental is located in a prime location, just 45 minutes from the theme parks and 30 minutes from the Kennedy Space Center and the nearby beaches.

The Treehouse At Danville - Geneva

Another unconventional stay in the Danville area, this treehouse has incredible amenities that will make you feel like a modern day Swiss Family Robinson on your next getaway.Complete with a tree trunk elevator, there is also a private shower, air-conditioning, and real toilet, meaning you aren’t sacrificing comforts for this treehouse stay. The 18 foot yurt has picturesque accent lighting that sets the mood.

Rejuvenation Retreat with Private Beach & Pool - Englewood

It’s hard to resist the charm of this unique beachfront A-frame in Ponte Vedra Beach, which can accommodate the whole gang and up to 13 guests. The chic 1970s home features funky decor and modern touches throughout, including a large kitchen and living area, while the outdoor deck is a private spot to enjoy the view. It’s the beach access you’re here for, and the hosts have stocked the house with plenty of beach necessities so you don’t have to bring your own. Adventurous travelers can enjoy kayaking, paddle boarding, or fishing on the river, while downtown St. Augustine is just 15 minutes away.

Get a Little Glam in a Retro Palm Beach-Style Boudoir - Winter Park

It’s hard not to be lured in by the retro Palm Beach-style decor at this stylish apartment in Winter Park. What looks like a boutique hotel or magazine for interior design, the charming space is an ode to Old Florida, showcasing coral decor and tropical fruit and flamingo motifs. It offers a full kitchen with all the necessities, as well as a cozy living room with cable TV, air conditioning and tranquil bedroom space with a queen-size bed and room-darkening shades. Free parking is also available on the premises.

13 Bedroom Great Escape Lakeside - Clermont

Accommodating up to a whopping 43 people, this massive 13-bedroom property is set on 10 acres of land in Clermont. The one-of-a-kind estate is a destination within itself, offering a pool with waterslides, lazy river, escape game room as well as a laser maze, theater, human foosball and soccer billiards. Featured on the Guinness Book of World Records, each room at this lavish estate is based around a popular game, such as Monopoly, Scrabble, Clue and Risk. Challenge your friends and family to a game in the family TV game show studio with interactive buzzers or enjoy the outdoors in one of the kayaks, three-person canoe or five-person pedal boat.

Private Barn Studio at Pura Vida Florida Farm - Vero Beach

If you’ve ever dreamed of waking up at a farm, here’s your chance. Home to beloved animals like “Sweetheart” the donkey and horses “Chance”, “Cimi” and “Teddy”, this 20-acre farm boasts a beautiful oak tree-lined driveway, catch-and-release pond and swing-set for kids. Your living space is on the second floor of the barn and has private access, with cozy spaces for eating, sleeping and relaxing.

Disney Themed Villa - Kissimmee

It wouldn’t be a list of holiday rentals in Florida without a Disney theme sprinkled in, and this whimsical Disney-themed villa in Kissimmee certainly does not disappoint. The extensive amount of details in the Frozen, Avengers, Tron and Harry Potter themed rooms are the real highlight, but the kids will also delight in the property’s Mickey’s 50’s Diner and Seven Dwarfs playhouse area in the back. Accommodating up to an astounding 15 people, the villa is conveniently located only 4 miles from Disney World and a short drive from Universal Studios, Sea World and other major attractions in Orlando. Both parents and kids alike can soak in the sunshine at the outdoor pool, and if the weather isn’t ideal, you can browse the DVD, books and video games available.

Treehouse Gypsy Palace, Direct Oceanfront - St. Augustine

One of the most unique treehouse rentals in Florida, this beachfront home offers a perfect location for ocean lovers. Split between 3 floors, the Airbnb features one bedroom, one bathroom, and an open living/kitchen area that can comfortably accommodate up to 4 guests. Just a few steps out onto the walkway and you’ll be at the ocean, enjoying interrupted ocean views and a glimpse of the dolphins splashing in the water.

Vintage '71 Airstream, Pool, Spa, Lanai & Beaches - Bradenton

Parked next to some of Florida’s most beautiful beaches on Anna Maria Island, this vintage 1971 Airstream is a perfect getaway for couples, solo adventurers and even furry friends (for a small fee). The remodeled Airstream is cozy as can be, offering a California king bed, lots of windows, a kitchen, storage compartments, air conditioning and a projector for movies. It’s parked beneath an oak tree canopy with a hangout area and next to a covered pool, hot tub and keystone coral fire pit.

The Beehive Treehouse - Orlando

This ultra-stylish treehouse Airbnb in Orlando has all the bells and whistles, including a Nespresso coffee maker, 80-inch TV, and a private balcony. There’s even an outdoor claw tub and custom-made chandelier, as well as AC for warm Florida nights. The living spaces are cozy with its plush leather couch, while a ladder leads to the comfy bed. Don’t forget about the vinyl record player and swing set that’s attached to the treehouse.

Houseboat - Sanford

Located within walking distance of Historic Sanford and its array of bars, restaurants and art galleries, this 60-foot “floating condo” is up for grabs for your next vacation rental. Docked at Lake Monroe Marina and part of the St. Johns River System, here you’ll have all the traditional amenities of a holiday rental with the added luxury of floating on Lake Monroe. With two bedrooms and three bathrooms, vacation-goers will have access kitchen appliances, stereos and TVs to ensure you have a comfortable stay. Wake up to watch the sunrise over the lake and birds fluttering about before taking a short pedal on the beach cruisers, go on a dinner cruise, or take a sailing class.

The Ritz - Orlando

Have you ever wanted to try tiny house living? This stylish tiny house in Orlando offers plenty of perks, including a full-size fridge, glass stove cooktop and an open floor plan with high ceilings. Don’t spend all your time indoors though, as this space is perfect for outdoor adventures, including fishing, kayaking and sunrise yoga by the lake. Accommodating up to five guests, the house is also pet-friendly. If the Ritz is not available for the dates you want, check out the host’s other listings, as they have multiple highly-rated tiny houses.

Luxury Villa With Drive-In Home Theater - Kissimmee

This over-the-top luxury seven-bedroom villa is the ultimate vacation getaway for families. Along with original theme rooms, it boasts a “drive-in” indoor theater with a projector entertainment system and classic car sofas, an arcade and a private pool. Located in the prestigious Reunion Resort, you’re within a short drive of Disney.

Quirky Studio, Steps to Beach & Restaurants - Gulfport

Both fun and quirky, this colorful Gulfport studio is a dream for beach lovers, located steps from both the popular Beach Blvd and Gulfport Beach, as well as the collection of eclectic shops Gulfport is known for. The light and bright artists studio comes with a Smart TV, Keurig coffee maker and dedicated parking space in addition to two beach chairs and a back patio with a peaceful garden.

The Spaceship House - Navarre Beach

If you’re a fan of the extraterrestrial, this unique spaceship house is sure to pique your interest. Your stay in this dome house will be out of this world, as the newly remodeled rental is decorated to look like a spaceship both inside and out. Perfect for Trekkies and Star Wars fans who like to pretend their traveling to galaxies far far away, the spaceship is also across the street from the beach and offers space bicycles to cruise the area.

Orlando Venice - Orlando

This pet-friendly tiny house in Orlando is Florida lake living at its finest, offering a roll-up garage door with double-paned windows that opens from a summer kitchen onto a covered patio. Enjoy the electric fireplace and open concept design, as well as the captivating panoramic views of Lake Fairview. Spend your days fishing and kayaking or wake up early and enjoy sunrise yoga by the lake.

The Tiki Suite - Key West

There’s truly no Airbnb like this one, an iconic Key West Tiki Suite that combines the best parts of boat life with the comforts of a modern home. It offers the ultimate glamping experience for those who love water with its tropical-themed exterior, cozy hammock, stand-up paddleboards and snorkel gear. Spotting wildlife like dolphins and manatees is common, while inside you’ll find a high vaulted ceiling, king-size bed, voice-controlled lighting, coffee maker and French doors that open up right onto the ocean.