Known for its tropical atmosphere, seafood restaurants, and memorable outdoor adventures, the Florida Keys are perfect for when you want an island escape. But the palm tree-filled scenery comes at a hefty price tag, as top hotels in the Keys often come with a higher price tag. Fortunately for budget-conscious travelers, there’s an alternative option: Airbnb. To help you make the most of your vacation in the Sunshine State, we’ve highlighted the coolest Airbnbs in the Florida Keys, from beachfront bungalows to waterfront getaways.
Waterfront Retreat with Boat Dock & Ocean Views - Islamorada
You can’t beat the views at this three-bedroom Airbnb in Islamorada, which is strictly set for long-term rentals (28+ nights) only. It’s the perfect getaway for those looking for a place to work remotely in Florida, offering incredible beach and ocean views from the family-friendly waterfront retreat. In addition to a sandy backyard that leads directly to the ocean, you’ll have access to a private boat dock, four beach cruises, a hammock, beach chairs, and a furnished screened-in patio.
Waterfront Cozy Cottage with Boat Ramp & Dock - Little Torch Key
You’ll be in a tropical paradise in this beautiful waterfront home, which features a 250-foot dock, ramp, and basin for your boat. Along with stunning panoramic water views, you will be just steps away from the ocean water. If you’re up for an adventure, you can even bring or rent fishing and snorkel gear to fish off the dock and explore the underwater scenery. Inside the home, there’s an open concept living and kitchen area, as well as welcomed parks like a Smart TV and relaxing heated massage recliner chair.
Gorgeous Ocean View Home - Marathon
Book a stay at this family-friendly ocean-view home for a memorable trip to the Florida Keys. It has a prime location in the heart of Marathon and is just a quick drive from the picturesque Sombrero Beach, where you can enjoy snorkeling, fishing, boating, scuba diving, and dining at its waterfront restaurants. The four-bedroom layout means you’ll have room for the entire gang, with a big living area, new appliances, and perks like a washer/dryer. Catch a sunset view from one of the two balconies or hang out in the beachy backyard with its cozy seating and BBQ grill.
Captain’s Quarters Ahoy Mateys - Key Colony Beach
Located in Key Colony, Marathon, this spacious two-bedroom duplex is surrounded by water. While you’ll be close to the best restaurants in the city, its tranquil space offers a much-needed getaway with its open water views. Lounge in the family room and take in the beautiful views of the bay or head to the Tiki Hut for an afternoon cocktail and kick back on the deck. Other amenities include sunning loungers and an outdoor gas grill, as well as an outdoor rain shower, bait and fish freezer, and fish cleaning station with light and water.
Sea Ray Cove @ Sombrero Beach, 75' Boat Dock - Marathon
Live a life of luxury in the Florida Keys ground-level waterfront home. With a recent facelift, the remodeled 3-bedroom (with bonus room) home is set in the famous Sombrero Beach neighborhood. You’ll be a block from the sandy beach shore, while inside the home is an open floor plan overlooking the in-ground pool deck and tiki hut. The home has a gas grill, cleaning table, and outdoor shower and bait freezer, as well as a 75-foot bulkhead with 120-volt electricity and water available for all your boating needs. Kids will Leo the foosball table, air hockey, pac-man arcade, and corn hole.
Tropical Sombrero Beach Getaway - Marathon
Close to Sombrero Beach, this 3-bedroom offers a prime location near Marathon’s top attractions. While Key West is just an hour away for a day trip, we’d understand if you want to stay on-site with the home’s private pool, dock, and backyard oasis. When you’re ready to go on an adventure, take advantage of the complimentary paddle board, bikes, and kayaks for your use.
Flakey's - Islamorada
Short for the Florida Keys, “Flakeys” offers you a slice of the Caribbean paradise in its two-bedroom home in Islamorada. There’s no need for a car here, as you can walk or bike to the best restaurants, bars, beaches, and shops on the island. You’ll find two balconies with rocking chairs so you can savor the few, as well as a beautiful backyard garden that is perfect for picnics. Its downstairs area has a calendar of events, including art classes, yoga, trivia, and lawn games.
Waterfront Home with 37.5-Foot Dock, Cabana Club Included - Key Colony Beach
Couples who love color will fall for this charming one-bedroom condo in Old Town, less than a block from Duval Street. It features a wrap-around porch with chairs, a spacious living room with a leather sofa and galley kitchen with bar seating as well as two flat-screen Smart TVs and Bluetooth stereo system. When you’re ready to explore, the Southernmost Point and Hemingway House are just a few blocks away.
Bella Vita - Key West
You can’t beat the views at this three-bedroom Airbnb in Islamorada, which is strictly set for long-term rentals (28+ nights or more) only. It’s the perfect getaway for those looking for a place to work remotely in Florida, offering incredible beach and ocean views from the family-friendly waterfront retreat. In addition to a sandy backyard that leads directly to the ocean, you’ll have access to a private boat dock, four beach cruises, a hammock, beach chairs, and a furnished screened-in patio.
Beach House with Private Pool & Dock, Gulf Sunset View - Marathon
A luxury beachfront getaway in Marathon, this two-bedroom rental has a private pool and dock as well as Gulf sunset views. Away from the traffic and noise of US Hwy #1, this secluded getaway has special features like a gourmet kitchen, luxury bedding, and a freshwater pool surrounded by lush gardens. Set in Grassy Key, it’s close enough to enjoy Marathon restaurants and dive sites in the Upper and Lower Keys.
4 Bed Sanctuary Villa With 35-Foot Dock & Private Pool - Duck Key
Escape to paradise at this beach bungalow, which features two bedrooms, a 60-foot private dock, and easy ocean access. In addition to a fully equipped kitchen with new appliances and a spacious living and dining area, it features a BBQ grill, boat trailer parking, and beautiful views of the water. The unique A-frame home has lots of character, offering a tranquil backyard oasis where you can relax on a sun lounger and take in the tropical views.
Modern Beach Tiny House with Tiki Hut & Boat Dock - Key Largo
Located in Marathon, this two-bedroom condo Airbnb has a prime location in the Florida Keys. Set within a family-oriented island community, the rental includes inviting perks such as a private balcony, full kitchen, and washer/dryer. Accommodating up to six guests with a queen sleeper sofa in the living room, groups can enjoy endless activities, as canoes, kayaks, and bikes are available for guest use. There’s also a swimming pool, shuffleboard, tennis courts, and BBQ grills onsite.
Peaceful, Newly Renovated Condo With Boat-Slip - Marathon
This newly renovated condo offers everything you’d need for a Florida Keys vacation. The 2nd story rental has beautiful views of the canal, access to a saltwater pool, as well as a private 40-foot boat slip so you can bring along your boat with you. The condo itself has a king-size memory foam mattress ensuring a peaceful night of sleep and a well-stocked kitchen when you’re not exploring Marathon’s local restaurants. The canal takes you right out to the ocean, where you’ll find some of the best fishing and reefs in the country. The hosts even provide two inflatable paddle boards and two bikes.
Tiny House on the Water - Key Largo
Discover a prime location at this Key West gem, just a short walk from Mallory Square, Duval Street and Zachary Taylor Park, popular for swimming, snorkeling and relaxing on hammocks. The one-bedroom unit is located in a gated community, which has a heated pool, while the covered deck is perfect for enjoying a glass of wine or a cup of coffee. If you want to cruise on two wheels, there’s rental bikes available.
Mermaid Cove - Key West
Technically this is no longer listed on Airbnb, but the oldest operating guesthouse in Key West, the Island City House Hotel boasts a rich history, a part of the Key West Historic Market Tour. The three-story Victorian mansion was originally built as a private home for a wealthy Charleston merchant family in 1880, then converted into a hotel in 1912 in anticipation of the railroad’s arrival. The suite is furnished with Victorian antiques, lace curtains and hardwood floors, while a sparkling pool, infrared sauna and large sunning deck are adding perks.
Oceanfront with Dock, Hot Tub & Secluded - Marathon
Embodying “Old Keys” living, this peaceful rental property is a quaint one-bedroom oceanfront cottage. Located on Grassy Key, it’s just a 10-minute drive from the city of Marathon and far enough from the hustle and bustle to make you feel like you’re on island time. Surrounded by lush landscaping, it features a 6-person hot tub for a massage after your all-day adventures, while a scenic stroll and nap in the hammock will surely melt your worries away.
It's Tiki Time in the Florida Keys - Tavernier
With a gorgeous interior, this one-bedroom condo is perfect for couples or small families. Recently renovated, it’s located in the gated Ocean Pointe resort in the nature isle of Tavernier. In addition to its colorful mid-century modern tropical decor, you enjoy all the luxury of being within a resort, including a swimming pool surrounded by sun loungers, a pool bar, and a private sandy beach. Bring binoculars to enjoy the view of the nature conservation area from the balcony.
Tropical Paradise: The Reef Marathon 2-Bedroom Villa - Marathon
Located a few blocks from Duval Street, this private room features a king-size bed, flat-screen TV, complimentary Wi-Fi and a private bathroom. Embrace the Florida Keys tropical vibe at the two outdoor pools and Jacuzzi, then sip cocktails from the on-site bar or grab a pick-me-up Starbucks coffee. Continental breakfast comes with the room as a part of The Southernmost Inn, and adults-only property.
Walking Distance to Beach - Key West
Discover a prime location at this Key West gem, just a short walk from Mallory Square, Duval Street, and Zachary Taylor Park, popular for swimming, snorkeling, and relaxing on hammocks. The one-bedroom unit is located in a gated community, which has a heated pool, while the covered deck is perfect for enjoying a glass of wine or a cup of coffee. If you want to cruise on two wheels, there are rental bikes available.
Charming Cottage on the Water, with Kayaks - Key Largo
Only about an hour from Miami’s top attractions, you can embrace tiny home living in this tiny house in Key Largo, where you’ll be located within a private community with two beach areas, a boat ramp and a heated swimming pool. Enjoy beach volleyball, let the kids loose at the children’s play area and entertain at the gazebo with two large dining tables. Active travelers will appreciate the two kayaks and standup paddleboards for guests.
