Discover the best Florida Keys cottage rentals. Enjoy a tropical paradise with top-rated stays in prime locations across the Keys.
The Florida Keys, a string of tropical islands stretching between the Atlantic Ocean and the Gulf of Mexico, are a haven for sun-seekers, adventurers, and anyone looking to escape to paradise.ย
Known for their crystal-clear waters, vibrant coral reefs, and laid-back vibe, the Keys likewise offer a variety of unique cottage rentals that cater to every type of traveler.
From the bustling streets of Key West to the serene beaches of Key Largo, let’s explore the best Florida Keys cottage rentals that promise an unforgettable vacation!

Best Florida Keys Cottage Rentals in Key West
Key West, the southernmost city in the continental United States, is famous for its lively atmosphere and historical charm. The spot also boasts an impressive statistic: itโs the southernmost point of the continental USA, providing stunning sunset views.ย
Staying at The Duval Home or Sunset Key Cottages puts you right in the heart of this vibrant island.
Fun fact: Ernest Hemingway’s house, now a museum, is a must-visit spot, giving you a glimpse into the life of the legendary author.
Now as we leave the excitement of Key West, let’s venture to the serene heart of the Keys, Marathon, next!
Marathonโs Coastal Charm: Top Cottage Rentals
Marathon, known as the โHeart of the Keys,โ offers some of the top Keys rentals for those looking to unwind in a more relaxed setting. The Seven Mile Bridge, once one of the longest bridges in the world, is a notable landmark in Marathon.ย
Accommodations like Yacht Haven Marina and Indigo Reef Resort provide luxurious stays with beautiful views and easy access to the water.
Fun fact: Marathonโs central location makes it an ideal spot for exploring both the upper and lower Keys.
And speaking of prime locations, letโs next explore the fishing paradise of Islamorada.

Sport Fishing Paradise in Islamorada
Islamorada, known as the โSport Fishing Capital of the World,โ is a dream destination for anglers and water enthusiasts. Islamorada is also home to the โTheater of the Sea,โ a marine mammal park where visitors can interact with dolphins and sea lions.ย
Staying at The Caribbean Resort or Cheeca Lodge & Spa will surely offer you a blend of luxury and adventure, with direct access to some of the best fishing spots.
Fun fact: Islamoradaโs vibrant marine life and crystal-clear waters make it a premier destination for snorkeling and diving.ย
And from the sport fishing capital, letโs head over to the northernmost island of the KeysโKey Largo.
Scenic Retreats in Key Largo
Key Largo, the first and northernmost of the Florida Keys, is famous for its underwater attractions and serene landscapes. Key Largo is home to John Pennekamp Coral Reef State Park, the first underwater park in the U.S., providing unparalleled opportunities for snorkeling and diving.ย
Here, properties like Kona Kai Resort and Marina Del Mar Resort offer idyllic stays with easy access to the ocean.
Fun fact: Key Largoโs coral reefs are among the most diverse and well-preserved in the world, making it a must-visit for marine life enthusiasts.

Unlock Your Florida Keys Adventure
From the bustling charm of Key West to the serene beauty of Key Largo, the Florida Keys offer a diverse range of cottage rentals that cater to every travelerโs dream.ย
Whether youโre fishing in Islamorada, exploring the historic streets of Key West, or diving in the coral reefs of Key Largo, the Keys promise an unforgettable tropical getaway.
With that, we suggest you go and pack your bags and get ready to unlock your Florida Keys adventure with Vacation Cottages.ย
Paradise is just waiting for you!