Stay Where It's Easiest To Eat, Drink And Play

In Key West, stay where it's easiest to eat, drink and play. For starters, cars are few, and speed limits are low, so set your pace to enjoy our natural paradise, its cool architecture, hip and happy hangouts, and the local characters you’ll meet along the way. Our southernmost paradise measures about four miles by two and it’s flat, so you’ll have an easy go of it. Our collection of luxury boutique vacation rentals dot all around Key West. You're sure to find just the right one to complement your list of exciting Caribbean adventures. Here are a few we recommend for you this summer.

Located on a tiny, quiet Old Town Lane which is a 5-minute walk to Duval Street, Bahama Getaway is also a 15-minute walk to Ft Zachary Taylor State Beach, and an 8-minute walk to the free community pool where you can swim laps, free swim, or take an exercise class. There are several amazing restaurants within a two-block radius including Blue Heaven, Le Creperie, Santiago's Bodega, Firefly, and the Blue Macaw.

In Old Town, North of Truman, you'll find a majority of the Key West tourist attractions as well as numerous restaurants, shops and galleries. The neighborhood boasts historic homes, shotgun and conch-style homes like our Cayo Limon. You'll be mere blocks from all the must-see Key West attractions, as well as fine dining and shopping, and only one block from world-famous Duval Street. Walk to Nancy Forrester's Secret Garden and the Hemingway House and Museum, then make your way to the Key West Lighthouse and Fort Zachary Taylor Historic State Park. And be sure to catch the parades and celebrations that occur in the area throughout the year.

My Happy Place is just minutes to the beautiful Key West Cemetery in one direction, and for less than a short walk to Duval Street, you’re in the heart of Key West. Margaritaville and Sloppy Joe’s are just minutes away! It's in heart of Old Town, just 2.5 blocks to world-famous Duval Street.

Located in the far Northeast corner of Old Town, the luxury residences at Steamplant are at the front of the Historic Seaport and central to all that Key West has to offer. Take an evening stroll along the Historic Seaport and enjoy the variety of restaurants, bars, boutiques, and marinas. A 9-minute walk takes you to Duval Street where locals and visitors alike enjoy world-class restaurants, live music, art, and live stage theater.

Old Town is the western part of the island and is divided into North and South of Truman Avenue. When you stay at Solaris Cottage, there’s no need for a car. Take a leisurely walk or one-minute bike ride and you’re just where you want to be. A majority of the best Key West tourist attractions are located here as well as numerous restaurants, shops and galleries. DJ's Clam Shack, Antonia's Italian, and all the good things Duval Street has to offer are here. Mallory Square is a 5-minute bike ride for those fabulous sunset parties.

Villa Luxe is nestled in a perfect location that's just a few steps from the world-famous Duval Street and walking distance to hot spots like Higgs Beach, the Southernmost Point, Ernest Hemingway Museum, coffee shops, bars, and ample restaurants.

This is one tropical paradise that will captivate you while roaming through one of the prettiest towns in the United States. Stay where it's easiest to eat, drink and play. Find all of your best options online with Historic Key West Vacation Rentals!