Florida Keys Vacation Rentals
Compare 288 vacation rentals.
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Float into laid-back island life, where sun-soaked afternoons, gentle ocean breezes, and freshly caught seafood are part of the daily rhythm. Whether you're paddleboarding through mangroves in Islamorada or catching sunsets in Key West, Vacasa vacation rentals offer a private retreat to match any Florida Keys state of mind — from casual cottages to luxe waterfront homes.
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Yes, 107 of our Florida Keys homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).
Browse dog-friendly homes >Yes. 288 of our Florida Keys vacation rentals have internet access, so you can stay connected throughout your trip.
Browse homes with internet access >Absolutely. Our local Florida Keys team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.
Learn more about Vacasa Premium Clean >Book your Florida Keys vacation rental today and experience island life on your terms.
Browse Florida Keys Vacation RentalsThe Florida Keys are more than just sand and sunsets. Each island offers its own story, from natural wonders and wildlife to unforgettable adventures and island culture.
Begin in Key Largo, the first Key travelers encounter. Here you’ll find John Pennekamp Coral Reef State Park, the country’s first underwater park—ideal for snorkeling, kayaking, and exploring vibrant marine life beneath the surface.
In Islamorada, life moves slower. Feed the tarpon at Robbie’s Marina, savor fresh seafood with dockside views, or browse galleries that showcase the island’s artistic flair. It's a perfect blend of quiet charm and ocean adventure.
Over in Marathon, families enjoy the Dolphin Research Center and gentle beaches. You'll find oceanfront homes and easy access to treasured sites like the historic Seven Mile Bridge, where sunrises shimmer across endless water.
Big Pine Key introduces a wilder side of the Keys. Spot rare Key deer at the National Key Deer Refuge or search for seashells at tranquil beaches in Bahia Honda State Park, known for some of the clearest waters in Florida.
Finally, Key West invites you to immerse yourself in culture, color, and history. Visit the Ernest Hemingway Home, join the Sunset Celebration at Mallory Square, or wander Duval Street’s mix of live music, island eats, and boutiques.
No matter where you stay, each Key offers a world of its own—ready to make your trip truly unforgettable.
Each island in the Florida Keys has its own unique vibe — from laid-back and quiet to vibrant and lively. Here’s a quick guide to help you choose the perfect spot for your next tropical getaway:
Not sure where to begin? Start with one of the three regions of the Keys:
Choose from an array of professionally managed homes and condos across the islands. Each rental is thoughtfully outfitted for comfort and connection — with features like:
