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Check out our best selection of boat rentals in Key West! Florida’s world-renowned boating paradise is expecting you with so many attractions to choose from. You can either go for a day trip on an elegant sailboat or a sleek Key West catamaran rental, or book a week-long sailing vacation from Miami.

If you’re planning to spend a few days in the Florida Keys, do not miss the chance to enjoy the breath-taking sunsets sipping cocktails aboard your own Sailo private charter. Another great idea to spend time on the water with your family or friend is a snorkeling trip on one of our premium boat rentals in Key West.

Weather and boating in Florida Keys

You should always keep in mind the weather when you’re looking to charter a catamaran or a sailboat in the Florida Keys. With winters ranging in the 70°s and summers in the 90°s with quite high humidity, there’s no wrong time to visit this tropical boating paradise. While weather is typically warm and calm, pay attention to the forecast leading up to your trip. If you’re traveling in the cooler months of the year, be sure to pack some layers to wear while on one of our boat rentals in Key West, especially if you plan to be on a sailboat for a sunset cruise.

When planning to rent a boat in this part of Florida, you should also pay attention to the wind patterns, which can vary from light and breezy in the summer to slightly stronger throughout the rest of the year. Dress accordingly when you go out on the water when travelling during those months. The wind shouldn’t have much of an affect on your boating adventure on a Sailo sailboat or catamaran rental in Key West as long as you prepare yourself for what to expect while out on the water.

The amazing Florida Keys are calling your name! Browse our best deals for boat rentals in Key West, FL: sailboats, catamaran and motor yacht charters, available for a day or for a week, available with captain included or as bareboats.

Departure date

Trip duration

Day trip

Multiple days
(Less than 1 week)

Weekly trip

Boat type

Boat length: 5ft -

Price: $ - $

Captain

Manufacturer

Boat model

Boat build year: -

Amenities

Boat rentals in Key West, FL 33040, USA

Key West, FL

boating guide

Departure date

Trip duration

Day trip

Multiple days (Less than 1 week)

Weekly trip Show boats that have weekly prices. Most weekly boats outside of the US are available only Saturday to Saturday.

Boat type

Boat length: 5ft -

Manufacturer

Boat model

Price

Captain

Boat build year: -

Amenities

Departure date

Trip duration

Day trip

Multiple days (Less than 1 week)

Weekly trip

Boat type

Boat length: 5ft -

Price: $ - $

Captain

Manufacturer

Boat model

Boat build year: -

Amenities

Boat rentals in Key West, FL 33040, USA

Key West, FL

boating guide

Multiple days
(Less than 1 week)

Weekly trip
Show boats that have weekly prices. Most weekly boats outside of the US are available only Saturday to Saturday.

Multiple days
(Less than 1 week)