A fantastic vacation in Key West starts with renting a condo

With a total land mass of just 5.6 square miles, Florida’s Key West is certainly small. And the main island itself is even smaller, spanning just over 4 square miles. But don’t be fooled by its size: the southernmost city in the contiguous US is a top vacation destination with a ton to see and do, from historic tours and museum visits to swimming and snorkeling along the beach to simply wandering the streets, taking in the colorful houses and other unique sights, sounds, and tastes of the town. No matter where your interests lie, Key West surely won’t disappoint.

The best time of year to rent a condo in Key West

The island enjoys temperate climes all year round, and even if you’re looking to dip your toes into the ocean in the dead of winter, the water will be warm. But like many popular vacation spots, it gets rather busy (and pricey) in December, January, and February, with vacationers wanting to escape the dreadful weather back home. If you’re willing to brave hurricane season, which goes from June to November, you may have a fair amount of rain, but the rates will be cheaper and there’s still plenty to do. March through May, however, may be the sweet spot, where the weather is fair and the prices slightly cheaper than during the high season.

Top neighborhoods for Key West condo rentals

Key West may be tiny, but it’s a cultural and historical gem and one of Florida’s top vacation destinations. Whether you’re looking for a romantic getaway, a family-friendly vacation, or a fun-filled time with friends, Key West has it all. And no matter how long you plan to stay—a few days, a week, a month, or even longer—you’ll have no trouble finding the perfect place to lay your head and call home for awhile. From resort-style condos to small town homes and cozy cottage studios, there’s something in Key West for everyone. To jumpstart your search, check out these 3 fantastic neighborhoods with plenty of rental options.

Rent a condo in the Truman Annex

Exclusive and gated yet only a couple minutes’ walk from Duval Street, the Truman Annex is ideal for vacationers who cherish the quiet, but still want to be close to the action. It’s right in the heart of Old Town, so visiting all the historical and cultural attractions is easy. (The Harry S. Truman Little White House is actually on the premises.) Once a naval base, the grounds have been transformed into beautiful garden-like oasis filled with 1- and 2-bedroom condos and vacation homes, complete with picket fences, private balconies or porches, lush greenery, and fountains. There's also a community pool and complimentary parking—a luxury in Old Town, where parking can be difficult to find. And just outside the gate, you’ll find Fort Zachary Taylor State Park and one of Key West’s most stunning beaches, where you can spend the day snorkeling, swimming, picnicking, and more.

Reserve a cottage-style studio in Historic Seaport

Also in Old Town is the Historic Seaport — or the Bight. Once an important maritime trading center, the seaport is now brimming with quirky shops, bars, and delicious seafood restaurants. The rentals tend to be cozy cottage-style studios or have 1-2 bedrooms. Shared pools and outdoor grills are also common. However, parking is limited, and while places offer it, you may need to pay extra. Even so, you’re in the center of it all, so getting around without a car is easy. Fuel up for the day with a Cuban coffee before exploring all that Old Town has to offer, including the Ernest Hemingway House and iconic lighthouse. Then make your way over to Mallory Square for the Key West Sunset Celebration, a nightly festival where the beautiful sunset over the water takes center stage. Nearby Duval Street is also always buzzing with restaurants and nightlife options, so you won’t lack for entertainment!

Enjoy resort-style amenities in condos near Smathers Beach

For a beachfront vacation rental where you can easily step outside of your home and dig your toes into the sand, your best bet is to look near Smathers Beach, the largest public beach in Key West and a top spot for kayaking, paddleboarding, and other water sports. The area is more residential and a bit farther away from the hustle and bustle, but there are still plenty of shops and dining options. Plus, you’re only a few minutes by car or bike from Duval Street and the popular attractions in Old Town. Condo rentals here are a bit more spacious and luxurious, with complexes like the 1800 Atlantic and the Key West Beach Club offering fantastic views of the Atlantic Ocean from private balconies, a resort-style community pool and Jacuzzi, tennis courts, a gym, BBQ grills, and direct access to the beach.