Florida Keys Vacation Rentals: Houses & Condos

Welcome to Florida Keys Vacation Rentals! Here, you’ll find everything you need here to plan the perfect Florida Keys trip, an absolutely wonderful vacation destination at any time of year.

Florida Keys Vacation Rentals is dedicated to helping visitors plan and enjoy their vacation. Use the Advanced Search feature to quickly locate your ideal vacation holiday home. Select among one of the largest collections of Keys vacation properties from Key Largo to Key West and everywhere in between. Or, contact one of our rental agents who’ll walk you through your best vacation home choices based on your interests and requirements. You’ll find options to meet every need and budget.

We have vacation rental single family homes, townhomes, and condos for rent in the Florida Keys including each of the five main regions: Key Largo, Islamorada, the Middle Keys, the Lower Keys, and Key West.

Map of areas served by Florida Keys Vacation Rentals

The Key Largo area includes Key Largo and Tavernier. Islamorada residences are found on the islands of Plantation Key, Windley Key and Upper and Lower Matecumbe Keys. (Key Largo and Islamorada, together, are also referenced as the Upper Keys.) The Middle Keys designation encompasses Layton/Long Key, Duck Key, Grassy Key, Key Colony Beach, and Marathon. Proceeding southwest, the Lower Keys begins at Big Pine Key, and also includes Little Torch Key, Ramrod Key, Summerland Key, Cudjoe Key, Sugarloaf Key and Baypoint. The Key West area runs from Shark Key down to Key West passing through Big Coppitt, Geiger Key, Rockland Key and Stock Island en route.

Here’s a sampling of what lies in store for you:

The islands of the Florida Keys are connected by the Overseas Highway and forty-two bridges spanning over 100 miles. In fact, once you’re in The Keys, getting there becomes a lot of the fun. The Overseas Highway (a.k.a. US-1) which takes you from Key Largo to Key West is designated one of the very few All-American Roads by the U.S. Department of Transportation. As they put it, “The Florida Keys Scenic Highway travels through some of the nation’s most spectacular scenery…From the moment you reach the top of Key Largo’s Jewfish Creek Bridge on US-1 traveling south, the feeling of escaping the pressures of daily life by traveling to ‘the islands’ overtakes you. Come experience outstanding natural beauty, world-class fishing and diving, festivals, sunset celebrations, state and national parks, water sports, historic sites, museums, island cuisine, sunshine, tropical atmosphere, rich cultural heritage and friendly people that enjoy the laid-back lifestyle of the Florida Keys.”

Here are just a few of the attractions and things to do you’ll encounter on your drive down The Keys: After you cross over the Jewfish Creek Bridge at the Northeast entry to The Keys on the 18-Mile Stretch, you’ll discover Key Largo known for the John Pennekamp Coral Reef State Park and Key Largo’s premier fishing and SCUBA diving charters. Care to swim with dolphins, go eco-touring, visit the African Queen (the actual boat made famous in the Bogart-Hepburn film classic), dive on sunken wrecks, or relax watching the sunset from a waterfront table? Key Largo is the place. Home to a national park and a portion of the national marine sanctuary, along with two state parks, and tropical hardwoods, Key Largo is a natural wonderland. Many visitors find everything they want right there.

Heading down the Overseas Highway, you’ll find Islamorada, a Village of Islands. As an angler’s paradise, with an unmatched variety of marine species large and small within minutes of its coastline, Islamorada earns the title of The Sportfishing Capital of the World daily. In addition to its excellent dining and shopping, Islamorada is home to attractions such as the Theater of the Sea marine-mammal park, the History of Diving Museum, the forty-acre Founder’s Park with one of The Keys’ most scenic beaches, four state parks and a poignant monument to the devastating 1935 Labor Day hurricane.

Marathon, a 10-mile-long, family-oriented community at the center of the island chain, is called The Heart of the Florida Keys. Surrounded by the Gulf of Mexico on one side and the Atlantic Ocean on the other, Marathon is a paradise for water sports enthusiasts. The boating, fishing, diving, and snorkeling rank amongst the finest in the Florida Keys and can often be pursued right from the dock of many waterfront homes. Visitors to Marathon and nearby Key Colony Beach will also discover beautiful Sombrero Beach, the Dolphin Research Center, Crane Point Nature Center, golfing, tennis, stage and screen entertainment, fine dining and many shopping opportunities.

Taking drivers further down the island chain and into the Lower Keys is the Keys’ most famous structure, the Seven Mile Bridge. A marvel of modern engineering, it runs parallel to the original bridge built by Henry Flagler between 1909 and 1912 as part of his Overseas Railroad. It also hosts an annual race for 1,500 runners.

The next Overseas Highway point of interest is Bahia Honda State Park, where the 2.5-mile natural, white sand beach was once rated the number-one beach in the USA. Between Marathon and Key West, in the largely residential Lower Keys, you’ll find two national wildlife refuges, a national marine sanctuary and a state park. Big Pine Key is home to the National Key Deer refuge, a large expanse where the diminutive Key Deer live. Traveling through the Lower Keys is an exploration of open water vistas and gorgeous island habitats.

At the end of the Florida Keys island chain is Key West, the Southernmost City, one of the world’s most popular and surprisingly family-friendly vacation destinations. Key West has been home to pirates, Poet Laureates, Nobel Prize winners, and famous playwrights. Visit Ernest Hemingway’s home, the Key West Butterfly & Nature Conservatory, the Harry Truman Little White House, The Key West Eco-Discovery Center and Key West Aquarium. Take a ferry to Ft. Jefferson in the Dry Tortugas National Park. Enjoy all the watersports, entertainment, fine dining, shopping, lifestyle inclusiveness, theater, attractions and events that make Key West a place people want to return to again and again.

Browse our Keys Guide section to learn more about what each area of The Keys has to offer, plan activities before you arrive, and locate the local resources you’ll need while you’re here. Calendars, business directories, guides, restaurant reviews: it’s all there. View descriptions of attractions, sample our collection of useful links to Florida Keys guides and destinations, and check out the reviews other visitors left on Yelp about restaurants, entertainment, diving, fishing, shopping, nightlife and more.

Please contact us to make your reservation or with any questions you may have. We look forward to greeting you in The Keys!



Florida Keys Vacation Rentals: Featured Properties