The famous archipelago off the coast of Florida, the southernmost area of the continental United States, is a holiday hotspot. And Airbnb Florida Keys is the go-to option for anyone looking for a place to call home while vacationing here.
Around here, most homes and apartments for rent are right on the water. The Keys and their array of canals create a unique setting for boaters, watersports enthusiasts, fishermen and general beachgoers.
Islamorada is a sport fishing haven; Key West and Key Largo are well-known for their tourist-friendly main streets and social life. The tropical waters in the keys are also prime SCUBA territory. The marine life here is indeed abundant and colorful.
Explore the underwater state and coral parks, the legacy of pirate activity, and even Ernest Hemingway’s historic home. There’s truly something here for everyone.
Quick Breakdown of The Best Airbnbs in the Florida Keys
In a hurry to book? Check out my shortlist of ‘quick picks’ for vacation homes in the Florida Keys.
- Best Designer Vacation Rental in Marathon – Anglers Terrace, Private heated Pool, Rooftop Ter.
- Best Key West Airbnb in old Town – Big Blu – 5 bedroom, 4 bath in old town
- Best Cheap Rental on Key Largo – Newly Renovated Private Single House
- Best Unusual Airbnb Beyond the Beachfront – 1984, 32 foot Irwin sailboat “Sea Raven Six”
- Best Vacation Rental the FL Keys with a Private Beach – Private Pool-Dock, Canal Front, Beach!
The Florida Keys is a veritable holiday playground. I’ve added a few videos throughout the article to show some of the highlights from the area. Take a look for some ideas of what to see and do while you’re down there.
Top Airbnb Florida Keys Beachfront Rentals
Pack your snorkel and your suntan oil. Let’s dive into the Airbnb paradise that is the Florida Keys.
1) Anglers Terrace – Condé Nast Traveler’s Best Airbnb
Best Designer Vacation Rental in Marathon
Location: Marathon
Airbnb Plus: No
Superhost: Yes
Price: $250+ USD per night
https://www.airbnb.com/rooms/38514431
Thoughtful design counts for a lot. This beautiful white home uses its outdoor space to enhance a living area that’s already large and open. What could be better than having a kitchen and lounge that simply opens up one side of the house to a spacious deck and pristine blue pool? Why not rent a boat while you’re in the Keys and dock outside the house? The deck itself is right on the waterway, and it’s no surprise that much of the relaxation spaces are designed for full enjoyment of the outdoor offering.
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Guest Review: “This vacation was absolutely amazing. It was sheer perfection in every single way!”
2) Big Blu – 5 bedroom, 4 bath in old town
Best Key West Airbnb in Old Town
Location: Key West
Airbnb Plus: No
Superhost: Yes
Price: $700+ USD per night
https://www.airbnb.com/rooms/2285819
This is a shotgun house – a narrow architectural design, with all the rooms positioned one after the other. This one is slightly different to a traditional shotgun, though – it has an extraordinary 5 bedrooms – larger than usual. Two of these rooms are master suites with their own additional entrances. Try out that unique Chinese opium bed, play bocce on the lawn, or just relax in the enormous open living area. They’ve even left a couple of bicycles for your use, should you want to get out and about! The kitchen is also magnificent, with everything you might want or need, and all top of the line. Best of all, all 12 of you can sit at the dining room table and recount your day’s activities. Definitely a contender for best big group rental when it comes to Airbnb Key West, Florida.
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Guest Review: “Shawn’s place is beautiful! It is exactly as it appears in the photos. The skylight is a great bonus! The bikes are also a great amenity, we didn’t drive our car the entire weekend. It is the perfect space for an island getaway!”
3) Newly Renovated Private Single House
Best Cheap Rental on Key Largo
Location: Key Largo
Airbnb Plus: No
Superhost: Yes
Price: $110+ USD per night
https://www.airbnb.com/rooms/17796803
Key Largo is the closest Key to the mainland. This house, situated close to the local attractions, offers great conveniences for a beach vacation home, including an outdoor shower for those post-beach rinses. The kitchen is neat, well-supplied and attractively fitted. And the stilted design elevates the whole house for a more relaxed, luxurious feel. Large glass windows and doors light up the living space, and the deck is just perfect for a relaxing read over a cup of coffee.
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Guest Review: “This place is a special find, amazing stylish modern space with all the facilities you might need. The balconies are amazing to relax on in the evening.”
4) 1984, 32 foot Irwin sailboat “Sea Raven Six”
Best Unique Florida Keys Airbnb Beyond the Beachfront
Location: Key West
Airbnb Plus: No
Superhost: Yes
Price: $156+ USD per night
https://www.airbnb.com/rooms/3688936
Why not go all in, and just live on the water? This 32-foot sailboat offers that extra unusual something. And it’s a great option for a couple looking to have a romantic vacation. Aside from living on the boat itself, you get the use of kayaks for some outrides. The boat is berthed in a security resort for an added touch of privacy. And the marina resort includes pools, restaurants and a 2 mile beach. So you’ve got everything a regular holiday-maker would want, with an additional sense of marine adventure!
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Guest Review: I would stay on this boat again in a heartbeat! You can really tell that James and his family love the boat — it has everything you need for a restful stay plus a few loving touches.”
5) Private Pool-Dock, Canal Front, Beach!
“Best FL Keys with a Private Beach”
Location: Marathon
Airbnb Plus: No
Superhost: Yes
Price: $345+ USD per night
https://www.airbnb.com/rooms/37152742
This delightful 2-story home gathers the best characteristics of vacation homes in a neat package. This includes an appealing hammock by the poolside – always a plus in my book. Inside, bright oranges and blues add a playful flavor to the living space. Special mention must be made of the superb furnishings on the balcony deck. You’ll be tempted to spend most of your time here, sipping a cold drink in the shade, under the fan. When you venture beyond the pool, you can hang your legs over the pier, just touching the water.
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Guest Review: “This house was perfect for a week of fishing and relaxation! The home was stylish, comfortable, and was well appointed. The dock was perfect to have our boat behind the house and only about 15 minutes to get out to the ocean.”
6) Steps off Duval-Room with private deck
Location: Key West
Airbnb Plus: No
Superhost: Yes
Price: $234+ USD per night
https://www.airbnb.com/rooms/24350434
This room is one of only 6 at the Andrews Inn. The setting is absolutely gorgeous amid the lush palms and trees. It makes the drop into the queen sized bed that much more relaxing. There are added bonuses here. Like the free breakfast included in the rental. Stock up in the morning for a long day of sun and fun – and the bottomless mimosas are part of the deal! In the afternoon, the inn hosts a happy hour, which saves even more money. Best of all, you may meet another guest or two and start a new friendship! This is truly great value in the Key West Old Town.
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Guest Review: “It was amazing. Everyone was so nice. It was a great location. It was fun getting to know my neighbors at breakfast. Having bikes on the property was wonderful and easy. It was right next to the Hemingway house.”
7) Hidden Beach Duplex, Best Place in Key West
Location: Key West
Airbnb Plus: No
Superhost: Yes
Price: $439+ USD per night
https://www.airbnb.com/rooms/23999336
Hidden Beach is a natural beach – the only such one on Key West – and it’s private! This condo is touted as one of the best available for rent. I really love the fenced-in deck that really does come right up to the water. But just as appealing is the wicker styling of the decor – everything from the bed to the armchairs carries a theme that brings the whole place together. It’s not something often talked about, but it does add a sense of completion to a space. Beyond that, enjoy that private beach to your heart’s content. Walk up the pier to watch a sunset – it’s a definite highlight!
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Guest Review: “An astounding property. Right on the beach. They even have their own little private beach. The ocean view and the apartment are beautiful.”
8) Living the dream!
Location: Key West
Airbnb Plus: No
Superhost: No
Price: $225+ USD per night
https://www.airbnb.com/rooms/43424169
Not only does this gorgeous home have the requisite pool, but it’s also got sun cover that provides a glowing atmosphere to the pool area. It somehow makes a holiday here feel even more tropical and exotic. That’s not even mentioning the fountain that flows into it! You’ll want to spend time in this wood-finished kitchen too. It’s got all the modern amenities and connects aesthetically with the leather recliner feel of the living area. The aquarium in the living space adds a calm charm to the room, too.
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Guest Review: “We really enjoyed the outdoor space and spent the mornings watching the fish and the evenings in the hot tub. The house had all we needed to cook and a very nice grill to cook our fresh fish on!”
9) Gulf-front retreat with heated pool, hot tub, boat ramp & new dock!
Location: Marathon
Airbnb Plus: No
Superhost: No
Price: $685+ USD per night
https://www.airbnb.com/rooms/19309826
Where many homes in the keys are placed alongside the numerous canals, this one looks out over the open water, and has a near-300-foot pier that just seems to go out forever. Imagine sitting out by the fire pit in the evening, looking out over this paradise. During the day you can enjoy the pool, or just laze out under the palm trees on your very own estate. The size and amenities available here make it feel like you’re the sole occupant of a boutique waterside hotel. Of the many highlights, we loved the giant chess set on the beach, though it is hard to beat the private pier walk out into the middle of the ocean. Perfect for 8, but simply audacious for 2!
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Guest Review: “The home and the property were truly amazing. There was wildlife and amenities like kayaks, pool, hot tub and the dock that extend well into the Gulf.”
10) Vista Del Mar – 4 Bedroom 3.5 Bath Luxury Pool Home
Location: Marathon
Airbnb Plus: No
Superhost: No
Price: $700+ USD per night
https://www.airbnb.com/rooms/40866678
This incredible home was designed with an ambition to be the best in the Keys. If it isn’t, it’s very close. Two master suites offer choices, and that’s not counting the loft and the two secondary bedrooms. There’s also a terrace up on the 2nd floor, overlooking the ocean. But it’s the living space downstairs that really packs the punch. Whether you opt for social cooking in the kitchen, a cool beverage at the bar, or watching a game on the big screen, you’re in touch with each other! You will probably enjoy the pool most, though. Thoughtfully designed with an in-pool table and seating – so you don’t actually have to leave the pool to enjoy your drinks!
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Guest Review: “This house is perfect for a group of friends. Sooo much to do some days we didn’t even want to leave the house. Beautiful pool.”
11) P69 – 669 Corte Del Brisas
Location: Sombrero Beach, Marathon
Airbnb Plus: No
Superhost: No
Price: $539+ USD per night
https://www.airbnb.com/rooms/35145903
A veritable mansion for up to 10 guests. Remodeled with space in mind, it’s got 4 beds and 4 baths, a bright and airy kitchen with social gathering in mind. Of course, the outdoor lounge is a treat, where a sizable deck overlooks the pool. But the biggest plus here is the extra room on the lower level. It’s big and versatile. Let the kids hang out here, or just use it as a games room. Just outside the poolside area is a gas BBQ, and a dock just beyond the big old pool. Pure delight.
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Guest Review: “My husband and I rented this property for the first 2 weeks in December. We absolutely LOVED it and have booked it for the same period next year.”
12) Oceanfront Oasis – Pinch me am I dreaming!
Location: Islamorada
Airbnb Plus: No
Superhost: Yes
Price: $4050+ USD per night
https://www.airbnb.com/rooms/14431017
If it’s the look and feel of luxury you’re after, this de-facto mansion with its own private beach is your winner. Five beautiful bedrooms, a full-size lap-pool and its own elevator are just a few of the features setting it apart from the rest. Lots of extras included, too… paddleboards, bikes, kayaks – whatever you might need on an adventurous holiday. But the private beach is the kicker. There’s no one else but you here to enjoy the amazing Atlantic. Not sure why you’d even want to leave the property while you’re here. It’s quite possible to spend entire days in the hammock on the beach. Or at most in the private pool. Or in the ocean. You get the picture.
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Guest Review: “This home has amazing views. Right on the beach, just walk out the door and you are there. The heated pool is amazing. So nice to have a late-night swim under the stars with the moonlight shining on the ocean.”
13) 3/3 Village at Hawks Cay 5004 – TROPICAL SUN & FUN
Location: Duck Key
Airbnb Plus: No
Superhost: No
Price: $589+ USD per night
https://www.airbnb.com/rooms/40184598
The first thing that struck me here was the fantastic wallpaper in the living space. It’s so appropriate for this delightful home, pink and playful, gorgeous and bright. It feels like a house you’d live in beyond just a holiday. Rooms are light pastels – greens and blues. The splash pool is perfect for taking the edge off the heat. And the beach outside is just made for a short walk. Best of all, rental here includes access to the Cabana Beach Club, just a few minutes away by car.
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Guest Review: “We loved the warmth of the private pool and the ocean just steps away. The location is unbeatable. It is right near the entrance to Duck Key and is very accessible to all the amenities of the Keys. ”
Am I Missing Any Florida Keys Airbnbs Worth Mentioning?
Have you rented an incredible Airbnb in The Keys? If you know of any awesome vacation homes for rent, please let me know. You can reach out via email or my social media. I’m looking forward to hearing from you.
Other Recommended Reading…
If you’re looking at other options for your getaway, take a look at this list of awesome Airbnb options in the USA.
- The 17 Coolest & Best Airbnbs in Miami for the Ultimate Beach Getaway
- The 22 Coolest & Best Airbnbs in Hawaii for the Ultimate Vacation Experience
- The 19 Coolest & Best Airbnbs in Maine for a New England Getaway
- 19 Incredible Airbnbs Along the Oregon Coast: Cannon Beach & Beyond
- 17 Stunning Airbnbs in Tampa for the Ultimate Florida Getaway
- 15 Coolest & Best Airbnb Asheville Rentals in North Carolina
- The 20 Coolest & Best Airbnbs in Michigan for an Epic Great Lakes Getaway
- The 17 BEST Airbnbs in Las Vegas for all Budgets & Travelers
- The 17 Coolest & Best Airbnbs in Oahu for an Amazing Hawaii Vacation
- The 18 Coolest & Best Airbnbs in Colorado for a Rocky Mountain Getaway
- The 18 Coolest & Best Airbnbs in Dallas, Texas – Airbnb Dallas Guide
- Top 20 Coolest Airbnbs in Philadelphia, Pennsylvania
Final Thoughts on Florida Keys Airbnbs for Rent…
An Airbnb in the Keys, Florida is all about the warm equatorial weather, the ocean, and the sand. And the options here are varied, even if most of the best ones come with their own access to water. Why not try one of the superb mansions with their own beaches? Or maybe a quaint Keys cottage or more your style? They’re all here.
