Florida Keys Vacation Rentals
Explore Florida Keys vacation rentals with private pools, ocean views, beach access and laid-back island charm near boating, dining and clear blue water.
About our Florida Keys vacation rentals
Our Florida Keys vacation rentals are made for easy island escapes, with private pools, ocean views, waterfront terraces and laid-back locations close to beaches, boating, dining and clear blue water. From Islamorada villas to larger coastal homes for families and groups, these stays give you more space to relax after days spent fishing, snorkeling, paddleboarding or exploring the islands.
Many Florida Keys villas feature private outdoor areas, pool decks, open-air dining spaces, ocean or canal views, and easy access to the relaxed lifestyle that makes the Keys so popular. Stay close to Islamorada’s fishing charters and waterfront restaurants, plan day trips toward Key Largo, Marathon or Key West, or follow the Overseas Highway for one of Florida’s most scenic coastal drives.
Whether you’re planning a family vacation, romantic escape, pet-friendly break or winter sun getaway, our Florida Keys vacation rentals offer a comfortable way to enjoy this iconic island chain. With beachfront rentals, villas with pools and waterfront homes available, it’s easy to find a stay that suits your trip.
Popular Florida Keys vacation rentals
There are approximately 1700 islands that make up the Florida Keys, most of which are very small and unpopulated.
Key West International Airport (EYW) is the closest main airport to the Florida Keys, at a distance of 49 miles away.
The Atlantic hurricane season, which affects the Florida Keys, begins on June 1st and ends on November 30th, with the greatest chance of strong tropical storms between August 15th and October 1st.
The Florida Keys are home to many exceptional and beautiful beaches, including one in Bahia Honda State Park that was voted the second most beautiful in America.
The best place to stay in the Florida Keys depends on the type of trip you’re planning. Key Largo is great for snorkeling, diving and easy access from Miami, while Islamorada is ideal for fishing, boating and relaxed waterfront dining. Marathon is a good central choice for families and road trips, and Key West is best for nightlife, history, restaurants and sunset views.
Getting to and around the Florida Keys
Airports
The Florida Keys are served by two main airports. Key West International Airport (EYW) is the primary airport, conveniently located in Key West. Marathon also has an airport, the Florida Keys Marathon International Airport (MTH). Both airports offer domestic and limited international flights.
Taxis
Taxis are available at the airports and major towns in the Florida Keys. While they are metered, make sure to confirm the fare before starting your journey. Taxis are a convenient option for short distances and airport transfers.
Shuttles and Buses
The Florida Keys offer shuttle services and public buses that connect major islands. The Key West Transit operates in Key West, providing an affordable way to get around the city. Additionally, the Miami to Key West shuttle is available for those traveling from Miami.
Driving
Renting a car is a popular choice to explore the Florida Keys at your own pace. The scenic Overseas Highway (U.S. Highway 1) connects the main islands, offering breathtaking views along the route. Driving allows you to explore hidden gems and enjoy various attractions en-route.
Car Rental
Numerous car rental companies are available throughout the Florida Keys. Renting a car grants you the freedom to explore the islands' beautiful landscapes and discover off-the-beaten-path locations.
Whether you choose to fly, take a taxi, use public transportation, or rent a car, getting to and around the Florida Keys is convenient and allows you to experience the unique charm and natural beauty of this stunning archipelago.
Best time to visit Florida Keys
The best time to visit the Florida Keys is generally from December to April, when the weather is warm, sunny and less humid. This is one of the most popular times for beach vacations, boating, snorkeling and winter sun escapes.
For quieter stays, April, May and November can also be great months to visit, with warm weather and fewer crowds. June to November can be more affordable, but it falls within hurricane season, so flexible travel plans and travel insurance are worth considering.
Food and drink in the Florida Keys
Capture the essence of island life, blending fresh seafood, tropical flavors, and laid-back luxury. Local catches like lobster, grouper, mahi-mahi, and shrimp are often grilled, blackened, or served as ceviche, highlighting the region’s vibrant waters.
The Keys are also known for Key lime pie, fresh tropical fruits, and Caribbean-inspired dishes served in relaxed yet elegant waterfront restaurants. For drinks, enjoy craft cocktails, rum punches, frozen margaritas, and local beers while soaking up views of turquoise waters and stunning sunsets.
Whether dining casually on a pier or indulging in fine dining at a seaside villa, food and drink in the Florida Keys are a central part of the island’s luxurious, sun-soaked lifestyle.
Soak up the Florida Keys beachesRelax and indulge in the beaches of the Florida Keys, catering to all interests. Enjoy Bahia Honda State Park, Smathers Beach, Higgs Beach, Fort Zachary Taylor State Park Beach, and Sombrero Beach - to name a few!
Explore Key WestExperience Key West's laid-back vibe, historic sites, and vibrant nightlife. Discover the iconic Ernest Hemingway Home, enjoy sunset celebrations at Mallory Square, and shop and dine along lively Duval Street.
Snorkeling & DivingDive or snorkel into Florida Keys' underwater paradise, home to the only living coral barrier reef in the continental U.S. Explore renowned spots like John Pennekamp Coral Reef State Park and the Sombrero Reef.
Visit Dry Tortugas National ParkReachable by boat or seaplane from Key West, this remote island paradise showcases Fort Jefferson, a massive 19th-century coastal fortress. Set against a backdrop of crystal-clear waters, the scenic Park promises a unique day out!
FishingRenowned as a fishing destination, the Florida Keys offer opportunities for deep-sea and flats fishing. Both seasoned anglers and beginners can find exciting charters to suit!
Explore the Bahia Honda State ParkLocated in the Lower Keys, Bahia Honda State Park offers stunning beaches and plenty of wildlife spotting opportunities, with clear waters and nature trails leading to scenic viewpoints.
Visit the Dolphin Research CenterExplore the nonprofit Dolphin Research Center in Marathon, dedicated to marine mammal research and education. Engage and swim with dolphins, and interact with sea lions.
Tuck into some Key Lime PieDon't miss the famous Key lime pie when in the Florida Keys. Savor this sweet and tangy treat at various restaurants and bakeries across the islands.
Florida Keys' Concierge
When on vacation in the Florida Keys, you may be looking to make your stay extra special, as well as convenient. Our dedicated Concierge services invite you to make your vacation as effortless as can be, with a host of optional hotel concierge-style services.
From car hire and airport transportation to private chef hire, baby equipment hire, grocery shopping, welcome hampers, fishing charters and more, our custom Concierge services promise to enhance every moment of your Florida Keys vacation.
Beachfront rentals in Florida Keys
Our beachfront rentals in the Florida Keys offer the perfect base for a relaxed island escape, with clear waters, ocean views, and easy access to the sand. Set between the Atlantic Ocean and the Gulf of Mexico, the Florida Keys are ideal for beach days, boating, diving, snorkeling, fishing, and laid-back coastal living.
From scenic oceanfront homes to beach rentals with pool access, our Florida Keys beachfront rentals come in a range of sizes and styles. Choose from romantic seafront stays, family-friendly vacation homes, group rentals, and accessible properties designed for comfort and convenience.
Popular destinations such as Islamorada, Key West, and Key Largo offer everything from world-class sportfishing and coral reefs to fresh seafood, waterfront dining, and unforgettable sunsets. Whether you’re planning a peaceful beach break or an adventure-filled island vacation, our beachfront rentals in the Florida Keys put you close to the best of this iconic coastal destination.
Explore beachfront rentals in Florida Keys
Florida Keys pet-friendly rentals
Enjoy the beauty of the Sunshine State with your four-legged friend by your side in our Florida Keys pet-friendly rentals. Perfect for families, couples, and groups traveling with pets, these homes offer a comfortable base close to beaches, walking routes, waterfront spots, and the laid-back island lifestyle of the Keys.
Many of our pet-friendly rentals in the Florida Keys feature spacious layouts, private outdoor areas, private pools, and family-friendly amenities, giving everyone room to relax after days spent exploring the coast. Some homes are also wheelchair accessible, making it easier for the whole family to enjoy a memorable Florida Keys getaway together.
For larger groups, our spacious Florida Keys pet-friendly vacation rentals offer a stylish and practical setting for reunions, family vacations, and relaxed island escapes. With room for up to 8–10 guests in select homes, these rentals make it easy to unwind, reconnect, and enjoy the Florida Keys without leaving your pet behind.
Explore Florida Keys pet-friendly rentals
Florida Keys villas with pools
Our Florida Keys villas with pools are perfect for laid-back island vacations, giving families, couples and groups a private place to relax close to beaches, boating, dining and clear blue water. With spacious living areas, sun-soaked terraces, landscaped grounds and private swimming pools, these villas make it easy to cool off, unwind and enjoy the Florida Keys lifestyle at your own pace.
Many Florida Keys villas with pools feature indoor-outdoor living spaces, modern kitchens, shaded seating areas, outdoor dining spots and views of swaying palms, turquoise water or peaceful canals. Whether you’re staying near Key Largo, Islamorada, Marathon or Key West, a private pool gives you the perfect setting for slow mornings, afternoon swims and sunset drinks after a day on the water.
Ideal for family vacations, romantic escapes and group getaways, these villas combine comfort, privacy and tropical surroundings in one of Florida’s most scenic coastal destinations. From poolside days to snorkeling trips, fishing charters and island-hopping along the Overseas Highway, our Florida Keys villas with pools offer a relaxed and memorable way to experience the Keys.
