18 Coolest Airbnbs in the Florida Keys: Villas, Bungalows + More!

by Global Viewpoint
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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!

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Coolest Airbnbs in the Florida Keys pinterest photo
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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

Beautiful villa in Duck Key is among the best Airbnbs in the Florida Keys
A beautiful villa in Duck Key, Florida. | Credit: Airbnb
Beautiful villa in Duck Key
Credit: Airbnb

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

Windsor Townhome vacation rental in Key West
One of the coolest Airbnbs in the Florida Keys. | Credit: Airbnb
Key West townhouse
Credit: Airbnb

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

Palms Resort at Sugarloaf is among the coolest Airbnbs in the Florida Keys.
Palms Resort at Sugarloaf is a popular vacation rental for large groups. | Credit: Airbnb
Florida Keys vacation rental at Sugarloaf
Credit: Airbnb
Sugarloaf Florida Keys beachfront rental property
Credit: Airbnb

“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

Beach bungalow with Cabana Club access sunset picture
This beach bungalow is among the most unique Airbnbs in the Florida Keys. | Credit: Airbnb
beautiful bungalow with Cabana Club access
Credit: Airbnb

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

Casa Loca is one of the most unique Airbnbs in the Florida Keys
This Airbnb in Key West is perfect for groups of families/friends. | Credit: Airbnb
Casa Loca vacation rental in the Florida Keys
Credit: Airbnb
Beautiful pool area at the vacation rental
Credit: Airbnb

“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

Top notch vacation rental in the Florida Keys
This vacation rental in Marathon is among the best Airbnbs in the Florida Keys. | Credit: Airbnb
Vacation rental aerial views in Florida
Credit: Airbnb

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

One of the coolest Airbnbs in the Florida Keys (and Florida, in general)
A beautiful Airbnb vacation rental in the Florida Keys. | Credit: Airbnb
Extravagant interior decor
Credit: Airbnb

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

Spacious Airbnb in Key West, Florida
This luxury Airbnb in Florida will leave you speechless. | Credit: Airbnb
Outdoor patio in Key West vacation rental
Credit: Airbnb
Interior layout at Zesty Lime Airbnb rental
Credit: Airbnb

“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

Oasis in the Keys is among the top Airbnbs in Florida
A beautiful waterfront Airbnb in Marathon, Florida. | Credit: Airbnb
Florida vacation rental in Marathon
Credit: Airbnb

“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

Atlantis Oceanfront Cottage in the Florida Keys
An oceanfront retreat in the Florida Keys. | Credit: Airbnb
This is among the best Airbnbs in the Florida Keys
Credit: Airbnb

“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

Windswept Palms is among the most unique Airbnbs in Florida
A beautiful Airbnb in Key West right on the ocean. | Credit: Airbnb
Sweeping views of the Atlantic Ocean in Florida
Credit: Airbnb
Majestic views of the Windswept Palms in Florida
Credit: Airbnb

“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

Casa Palma Airbnb rental in Florida
A top notch vacation rental in the Florida Keys. | Credit: Airbnb
One of the coolest Airbnbs in the Florida Keys.
Credit: Airbnb
Lavish interior decor at the Casa Palma townhouse
Credit: Airbnb

“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

Island paradise Airbnb in the Florida Keys
An island paradise in the Florida Keys. | Credit: Airbnb
Florida Keys vacation rental on the beach
Credit: Airbnb
Beautiful historic home for rent in Florida
Credit: Airbnb

“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

Pelican Palms luxurious villa
A luxurious villa in Summerland Key, Florida. | Credit: Airbnb
beautiful Airbnb for large groups in Florida
Credit: Airbnb
Spacious pool area at the Pelican Palms
Credit: Airbnb

“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

Sunset bungalow Airbnb rental
Sunset bungalow Airbnb in the Florida Keys. | Credit: Airbnb
Unique vacation rentals in Florida
Credit: Airbnb
Stunning sunset bed and breakfast
Credit: Airbnb

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

Unique yacht Airbnb
This is definitely one of the most unique Airbnbs in the Florida Keys. | Credit: Airbnb
One of the coolest Airbnbs in the Florida Keys
Credit: Airbnb
Beautiful pool area on the Florida Keys
Credit: Airbnb

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

Casa Victoria old town villa
A luxury villa with lots of charm in the Florida Keys. | Credit: Airbnb
One of the most amazing Airbnbs in Key West.
Credit: Airbnb
Key West vacation rental
Credit: Airbnb

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

Waterfront Airbnb in the Florida keys with beach access
A stunning waterfront Airbnb in Marathon, Florida. | Credit: Airbnb
This luxury Airbnbs in Florida is on my Florida Keys travel bucket list
Credit: Airbnb

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

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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

– Top Beverly Hills Airbnbs

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