Where to Stay in the Florida Keys: Best Islands & Hotels

Best Places to Stay in Key West


Margaritaville Key West Resort – With fantastic views over the water and its location in the center of the Old Town (plus just three minutes from Mallory Square), this upscale resort is a fun and friendly place to stay. Rooms are spacious and boast private balconies and large windows – simply perfect for watching the boats pass by on the water outside. The outdoor pool here is accompanied by an open-air bar and there’s also a very chic restaurant on site, which welcomes diners from outside of the hotel for a lively atmosphere.

The Marker Waterfront Resort – A mere nine-minute walk from the food, drink, and entertainment at Mallory Square, The Marker Waterfront Resort was built in 2014, meaning a modern stay is what you can expect at this 4-star hotel. The staff here are friendly, there’s a decent pool for guests to use, and the rooms – including the bathrooms – are spacious. There’s more food and drink to be had just on the doorstep of The Marker, making it great for anyone wanting to explore Key West further.


Chelsea House Hotel – The best thing about this 3-star offering is the fact that it’s set over three beautiful period houses, making it great for anybody who likes to stay right in the middle of a town’s heritage itself. The Victorian era lodging comes complete with simple furnishings; some rooms have four-poster beds! The garden here is wonderfully shaded and comes complete with its own heated pool. When you can tear yourself away, the lively Duval Street is only a three-minute walk from the Chelsea House Hotel.

Truman Hotel – Bold, modern rooms decorated with marble are the order of the day at this 3-star offering, which also comes complete with a picturesque poolside area shaded by palm trees. Some rooms here come with balconies, so you can get some fresh air from the privacy of your own room, whilst suites feature a lounge. Parking is available at the Truman Hotel; it also boasts a complimentary continental breakfast for guests. The Ernest Hemingway House, an icon of the town, is just a three-minute walk away. Go To the Next Page to see more