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

Sort by:
Location
Reset
Dates
Filters
Reset

Departure date


Trip duration

Day trip
Multiple days
(Less than 1 week)
Weekly trip
Boat
Boat Details
Reset

Boat type

Boat length: 5ft -

Price: $ - $

Captain

Manufacturer

Boat model

Filters
Filters
Reset

Boat build year: -

Amenities

Boat Rentals in Key West, Florida

Map
Reset
Our destinations near Key West, FL

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

1 - 18 of 27 boats
  1. Home

Try Yacht Rentals in Key West, Florida with Sailo!

Are you looking for Key West boat rentals Airbnb? Check out our best selection of yacht rentals in Key West, FL! 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 Miami sailing vacation.

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 yacht charter in Key West. Another great idea to spend time on the water with your family or friend is a snorkeling trip on one of our luxury private boat rentals in Key West.

When to book a Key West boat charter in Florida?

You should  always keep in mind the weather when you’re looking for Key West catamaran charter or a sailboat rental in Key West, Florida. 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 private boat rentals in Key West, especially if you plan to be on a sailboat for a sunset cruise.

Boat Rental in Key West, Florida: best practices

When planning to rent a boat in Key West, 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 party yacht charters in Key West, Florida as long as you prepare yourself for what to expect while out on the water.

Key West Yacht Charters: Boat Types for Sailing

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