Looking to discover the best and coolest Airbnbs in the Florida Keys? Paradise awaits you.
The Florida Keys is a tropical oasis filled with endless beaches, sunshine, and outdoor adventures. It’s no wonder that the Florida Keys is also home to some of the coolest Airbnbs and vacation rentals in the state, ranging from exotic villas and bungalows to classic yachts and waterfront rentals.
In this article, we’ve ranked the best Airbnbs in the Florida Keys covering destinations like Key West, Siesta Key, Upper Sugarloaf Key, Marathon, Cudjoe Key, Summerland Key, and Duck Key, among others.
Whether you’re looking for a romantic getaway or a trip amongst family and friends, here are the 18 coolest Airbnbs in the Florida Keys!
First time using Airbnb? Here’s my coupon code to get $55 off your first booking!
Click here to save $55 with Airbnb!
The Coolest Airbnbs in the Florida Keys: Top Vacation Rentals in 2021
Here are the best Airbnbs in the Florida Keys by category, accounting for different amenities, trip types, and budgets. The following sections will cover each listing in more detail.
Top Airbnb in the Florida Keys: Oasis in the Florida Keys
Best Luxury Rental Florida Keys: Casa Loca in Key West
Top Romantic Airbnb in the Florida Keys: Beach Bungalow with Cabana Club Access
Best Florida Keys Airbnb for Large Groups: Casa Victoria Old Town Villa
Best Cheap Airbnb Florida Keys: Sunset Bungalow Rental
Top Airbnb Florida Keys with Pool: Windsor Townhome in Key West
Best Beach House Rental Florida Keys: Palms Resort at Sugarloaf
Most Unique Airbnb in the Florida Keys: Yacht Rental in the Florida Keys
The 18 Best Airbnbs to rent in the Florida Keys
If beach houses, romantic cottages, and luxury rentals all sound good to you, get excited! Below are some of the most unique stays in the Florida Keys:
1. Sanctuary Villa on Duck Key
Location: Duck Key, Florida
Rates from: $469 per night
Accommodates: 10 guests
Experience the best that the Sunshine State has to offer at this luxury villa in the Florida Keys. This unique Airbnb features 4 bedrooms for up to 10 guests, where you can take advantage of the private outdoor pool, back patio, and grill. Perfect for families and groups of friends. It’s also centrally located, making it the perfect homebase for exploring the Florida Keys.
Unique features: Private pool; 35-ft boat dock; lanai in master bedroom; outdoor patio; grill
Cool sights nearby: Hawks Cay Boulevard | Conch Keys | Dolphin Connection | Curry Hammock State Park
2. Windsor Townhome in Key West
Location: Key West, Florida
Rates from: $605 per night
Accommodates: 6 guests
Nothing says modern luxury quite like this villa in Key West. This vacation rental is equipped with a private garden and pool, spacious deck, en-suite bathroom with tub, and so much more. It’s situated in a charming Old Town neighborhood, where you’ll have plenty to see and do in the dive capital of the world.
Whether you’re looking for a family retreat, getaway with friends, or even a destination wedding party in the Florida Keys, this unique Airbnb in the Florida Keys has got you covered.
Unique features: 1,700 sq. ft. villa; heated pool; private garden; pool deck
Cool sights nearby: Duval Street | The Ernest Hemingway Home and Museum | Basilica of St. Mary Star of the Sea | Southernmost Point of the Continental US | Mallory Square
3. Palms Resort at Sugarloaf
Location: Upper Sugarloaf Key, Florida
Rates from: $860 per night
Accommodates: 8 guests
“One of a kind beach house with a private sandy beach, dock and boat dockage. A modern tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Gorgeous Ocean views. Natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree.” – Airbnb
With so much beauty and elegance, this is definitely among the most unique Airbnbs in the Florida Keys.
Unique features: Private beach access; ocean views; boat dock; pet-friendly; two gas grills; boats for rent
Cool sights nearby: Great White Heron National Wildlife Refuge | Melody Key | Saddlebunch Keys | Upper Sugarloaf Sound
4. Beach Bungalow with Cabana Club Access
Location: Key Colony Beach, Florida
Rates from: $275 per night
Accommodates: 4 guests
Is this one of the best Airbnbs in the Florida Keys? Probably. This beach bungalow offers the quintessential Florida experience with beautiful ocean views, modern amenities, and Cabana Club access. For what you get, it’s definitely one of the more affordable Airbnb vacation rentals in the Florida Keys. It’s also among the most romantic!
Unique features: A-frame home;ocean access; BBQ grill; boat trailer parking; 60-ft. dock
Cool sights nearby: Florida Keys Aquarium Encounters | Curry Hammock State Park | Coco Plum Beach | The Cabana Club | Sunset Park
5. Casa Loca Airbnb in Key West
Location: Key West, Florida
Rates from: $657 per night
Accommodates: 8 guests
“When you`re ready to escape the hustle and bustle of the real world why not enjoy the perfect alternative to a pricey luxury hotel. Our property is a luxury 3 bedroom, 2 1/2 bath in prime location. It has a heated, private swimming pool with all the amenities you can imagine. Once you take a look at this wonderful home, you’ll know you are in Paradise.” – Airbnb
Is this one of the most unique Airbnbs in the Florida Keys? I’d say so!
Unique features: Private pool; gas grill; concierge service; spacious porch
Cool sights nearby: Duval Street | The Ernest Hemingway Home and Museum | Smathers Beach| Southernmost Point of the Continental US | Mallory Square | Fort Zachary Taylor Historic State Park
6. Searenity Vacation Rental
Location: Marathon, Florida
Rates from: $290 per night
Accommodates: 6 guests
Experience the Florida Keys in style at this unique vacation rental in Marathon.
As one of the most romantic Airbnbs in the Florida Keys, this rental is beautifully decorated and decked out with all the essentials for a memorable tropical beach getaway. The location is perfect within a couple of minutes of the Gulf of Mexico. What more could you want in a Florida Keys Airbnb?
Unique features: Pool with jets; tiki hut; grill; two kayaks; two bikes; back porch; 30-ft. dock
Cool sights nearby: Sombrero Beach | Crane Point Hammock | Grassy Key | Dolphin Research Center | Turtle Hospital
7. Corte del Brisas Airbnb in the Florida Keys
Location: Marathon, Florida
Rates from: $374 per night
Accommodates: 10 guests
Take in the stunning tropical views from this incredibly cool Airbnb in the Florida Keys. This rental is in a beautiful Sombrero Beach neighborhood and comes with all the amenities to ensure a comfortable group stay. You won’t want to stay anywhere else!
Unique features: Close beach access; outdoor dining area; spacious balcony and deck; pool; propane gas grill; fish cleaning station; 50-ft. deep water dock
Cool sights nearby: Sombrero Beach | Crane Point Hammock | Florida Keys Aquarium Encounters | Dolphin Research Center
8. The Zesty Lime Airbnb in Key West
Location: Key West, Florida
Rates from: $690 per night
Accommodates: 8 guests
“Key West is known for all things lime: Key Lime Pies, Margaritas, and now, The Zesty Lime, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. The Zesty Lime includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom layout, a private pool, and plenty of space to stretch out or come together as a group. In addition to the fabulous layout and desirable amenities, this home has an unmatched location. The Zesty Lime is sure to make your group’s stay in Key West an extraordinary one.” – Airbnb
This beautiful accommodation is definitely one of the most unique Airbnb rentals in the Florida Keys.
Unique features: Private pool; outdoor dining area; patio; full time concierge service; propane BBQ grill; smart TV; pet-friendly
Cool sights nearby: Duval Street | The Ernest Hemingway Home and Museum | Historic Seaport| Southernmost Point of the Continental US | Key West Old Town | Fort Zachary Taylor Historic State Park
9. Oasis in the Keys
Location: Marathon, Florida
Rates from: $320 per night
Accommodates: 8 guests
“Boasting stunning floor-to-ceiling ocean views in every room, this newly remodeled home promises a delightful oceanfront stay in the Florida Keys. Use the four provided kayaks, two paddle boards for fun-filled explorations, or hop on the bikes to cruise the surrounding area. Enjoy a game of shuffleboard and full access to the famous Cabana Club, complete with a sparkling pool, hot tub, poolside concession and bar, a private beach and entertainment.” – Airbnb
Unique features: Oceanfront property; two kayaks; two paddleboards; Cabana Club access (pool, hot tub, private beach); patio; gas grill; fire pit
Cool sights nearby: Sombrero Beach | Crane Points Museums & Nature Center | Island Hoppers Aerial Adventures | Captain Hooks Marina
10. Atlantis Oceanfront Cottage Retreat
Location: Cudjoe Key, Florida
Rates from: $375 per night
Accommodates: 6 guests
“This Stylish, remodeled, open-concept home with refreshing coastal decor welcomes you to relax and enjoy the peaceful direct-ocean views, the rhythmic sounds of ocean waves & the rejuvenating, fresh ocean breezes! This vacation home is fully-equipped with all you need to entertain, or to unwind and relax. Waterfront lounging chairs, gas grill, a private 25″ boat slip out your front door, and a sea-wall swimming ladder to enjoy the ocean right from home! These are just a few of the amenities for you to enjoy while vacationing at Atlantis, Ocean-Front Cottage Retreat!” – Airbnb
Unique features: Oceanfront cottage; 25 ft. boat dock; heated pool; Jacuzzi; tennis and basketball courts
Cool sights nearby: Ramrod Key | Melody Key | Little Torch Key | Marvin Key
11. Windswept Palms at the Beach
Location: Key West, Florida
Rates from: $690 per night
Accommodates: 6 guests
“Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. Windswept Palms has been thoughtfully decorated and furnished. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. Windswept Palms is located within an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island.” – Airbnb
Unique features: Pool; beach access; Jacuzzi; picnic area with BBQs; fitness center; clay tennis courts; large balcony; Saunas
Cool sights nearby: Duval Street | Key West Butterfly and Nature Conservatory | Southernmost Point of the Continental US | Key West Lighthouse | Fort Zachary Taylor Historic State Park
12. Casa Palma Airbnb Rental in the Florida Keys
Location: Key Largo, Florida
Rates from: $280 per night
Accommodates: 6 guests
“Live the Lavish Keys Life in this newly remodeled Townhouse with lots of outdoor living/dining space! Our spacious two-bedroom, two-bath town home has been renovated from top to bottom with attention to detail and a modern contemporary flair. Take in the fresh air on one of our outdoor porches or patios or bring a glass of wine to watch the breathtaking sunsets from our oceanfront private beach or 400’ jetty.” – Airbnb
With so much to offer at a reasonable price, there’s truly no place like Casa Palma, one of the best Airbnbs in the Florida Keys.
Unique features: Boat ramp with ocean access; oceanfront private beach; two heated pools; two kayaks, Tiki huts; tennis courts; gas grill
Cool sights nearby: John Pennekamp Coral Reef State Park | Dolphins Plus Bayside | Dagny Johnson Key Largo Hammock Botanical State Park
13. Island Paradise Airbnb in the Florida Keys
Location: Key West, Florida
Rates from: $341 per night
Accommodates: 10 guests
“Beautifully restored historic home located on one of the most desirable and pristine blocks of William Street with over 2,000 sq. ft. of living space. Tranquil outdoor pool and walking distance away from the Key West Historic Seaport and Duval Street, fine dining, art galleries and museums.” – Airbnb
Brimming with history and charm, this is certainly among the most unique Airbnbs in the Florida Keys.
Unique features: Outdoor pool; self-check-in access code; patio; deluxe rooms; front porch
Cool sights nearby: Duval Street | The Ernest Hemingway Home and Museum | Southernmost Point of the Continental US | Mallory Square | Key West Historic Seaport
14. Pelican Palms Luxurious Villa
Location: Summerland Key, Florida
Rates from: $927 per night
Accommodates: 12 guests
“When you stay at the main home at Pelican Palms, you’re staying in a luxurious space unlike any beach house you’ve ever seen. You’re just a short walk from the water, but the shared pool is just as fabulous! Relax in a spacious living room, furnished with wood paneling and stone accents. The full kitchen will accommodate any of your cooking projects in a streamlined space. Cook up something delicious and enjoy it out on the extensively furnished patio. Afterwards, enjoy some Ping-Pong in the tiki hut. Younger guests will love relaxing in the loft space, though older guests may want to come up to take a spin on the piano.” – Airbnb
Unique features: Luxurious interior décor; pool; deck and patio area; ping pong; tiki hit; loft space
Cool sights nearby: Florida Keys Overseas Heritage Trail | Bahia Honda Key | Bahia Honda State Park | Little Torch Key | National Key Deer Refuge Nature Center | Blue Hole
15. Sunset Bungalow Airbnb Rental in the Florida Keys
Location: Summerland Key, Florida
Rates from: $251 per night
Accommodates: 6 guests
This beautiful bungalow is definitely among the coolest Airbnbs in the Florida Keys. Located on Summerland Key, it’s equipped with a private pool, bocce ball, outdoor chess, bikes, and kayaks where you can soak in the pristine ocean views. What more could you ask for in a luxury Airbnb in Florida?
Unique features: Private pool; kayaks; bikes; putting green; outdoor chess board; bocce; large outdoor deck
Cool sights nearby: Florida Keys Overseas Heritage Trail | Ramrod Key | Bahia Honda State Park | Little Torch Key | National Key Deer Refuge Nature Center | Sandspur Beach | Calusa Beach & Loggerhead Beach
16. Unique Yacht Airbnb in the Florida Keys
Location: Key West, Florida
Rates from: $353 per night
Accommodates: 6 guests
Ever dreamt of sleeping in a yacht in Florida? Then this unique Airbnb has got you covered. It’s 44 feet long and offers an amazing atmosphere like no other! You’ll be docked in a marina with easy access to the beach and not far from the downtown area. Enjoy the pool, gym, and sauna and the classic Key West vibes from this remodeled 1970 yacht. It’s definitely one of the coolest tropical Airbnbs out there!
Unique features: Large yacht; kayaks; pool; gym; grills; sauna
Cool sights nearby: Duval Street | The Ernest Hemingway Home and Museum | Southernmost Point of the Continental US | Truman Little White House | Key West Lighthouse | Key West Historic Seaport
17. Casa Victoria Old Town Villa
Location: Key West, Florida
Rates from: $1,363 per night
Accommodates: 12 guests
This is the perfect luxurious Airbnb in the Florida Keys for large groups. It’s decked out with all the tropical vacation essentials, including a private pool with a waterfall, covered porch and dining area, and extravagant suites to accommodate your entire group. With so much extravagance, Casa Victoria is among the most beautiful Airbnbs in the Florida Keys.
Read next: The most underrated places to visit in Florida
Unique features: Pool and waterfall; master suites; historic home in central location; Jacuzzi spa; propane BBQ grill; spacious yard and patio area
Cool sights nearby: Duval Street | The Ernest Hemingway Home and Museum | Southernmost Point of the Continental US | Key West Historic Seaport | Fort Zachary Taylor Historic State Park
18. Waterfront Airbnb in the Florida Keys
Location: Marathon, Florida
Rates from: $370 per night
Accommodates: 10 guests
Enjoy the calm ocean waters and serenity of the Florida Keys from this waterfront Airbnb. It’s decked out with all the essentials for a relaxing Florida getaway, especially for large groups of family/friends. This vacation rental is also in a great location, making it the perfect homebase for exploring the Florida Keys.
Unique features: Private beach area with tiki hut; private second-floor balcony; gas grill; deep water docking; smart TVs; no contact check-in; pool
Cool sights nearby: Sombrero Beach | Coco Plum Beach | Crane Point Hammock | Grassy Key | Dolphin Research Center | Knights Key
Best Airbnbs in the Florida Keys
Have you ever stayed in a unique Airbnb or vacation rental in the Florida Keys? Let me know in the comments or on Insta, as I’m always looking to add to this list of the coolest Airbnbs in the Florida Keys!
Looking to plan another luxury vacation? Check out these other destinations:
– Exotic Airbnb Mansions in Miami, FL
– Cool Airbnbs in the French Riviera
– Best Luxury Rentals in Europe
– Top Vacation Destinations in Florida
For further reading, check out my other East Coast articles:
