Key West, FL

A classic vacation rental market with a variety of real estate options and the highest rental rates in the Florida Keys, Key West boasts the steepest home prices on our list—but if you can navigate the licensing, it’s worth it.


The southernmost point in Florida, Key West is known for its charming architecture, spectacular reefs, vibrant nightlife, and laid-back island vibe. The tropical paradise that was once home to Hemingway now draws tourists from around the world to experience world-class kayaking, scuba diving, treasure hunting, and stunning sunsets. Vacation rental real estate options in Key West run the gamut from historic—Key West’s Old Town is home to one of the largest collections of Victorian homes in the U.S.—to classic Bahamian Conch houses, modern luxury condos, upscale beachfront villas, and quiet hideaways.

Insider tip

When it comes to Key West vacation rentals, guests prefer charming homes with a classic island vibe. Outdoor living is a huge part of life in the Florida Keys. Having a pool will boost bookings dramatically. Investors should also consider properties with outdoor seating areas where guests can enjoy the sunsets and ocean air. Before buying, familiarize yourself with Key West’s transient license rules. Homes that come with a transient license are more desirable for vacation rental properties, and they’re also more expensive. You can only get a transient license here by purchasing a home that already has one. Without this license, you’ll only be able to rent your new home on a monthly basis.

Learn more and compare Key West with other top markets in our insider's guide to the best places to buy a vacation rental.

Market size

1,000+ rental units

Median annual rental revenue


Median home price


Cap rate


*This document is for information and illustrative purposes only. It is not intended to provide “investment advice” or a “recommendation” regarding a course of action. The discussion is general in nature and has not taken into account your personal financial position or objectives. You should consult a licensed financial advisor or other professional to discuss your specific situation.

Estimated rental income figures and home sale prices are based on historical averages; for any specific property, the actual revenue, purchase price, and cap rate may differ materially from estimated amounts and depend on a wide range of factors outside Vacasa's knowledge or control, such as the property's condition, layout, and furnishings; expenses associated with the acquisition and ownership of the property (such as property taxes, utility fees, HOA fees, insurance fees, and mortgage-related expenses); rental calendar availability; existing and future regulations; current and future economic, social, and political trends and conditions; and weather and environmental factors. These estimates do not take into account the potential impact of state income taxes.

Vacasa makes no representations or warranties, express or implied, about the accuracy of this document. Furthermore, Vacasa has no obligation to update, modify or amend this document or to otherwise notify users in the event that any opinion, assumption, forecast or estimate set forth herein changes or subsequently becomes inaccurate. Therefore, you should not place undue reliance on statements in this document.

Vacasa offers property management and other real estate services directly and through licensed subsidiaries, including Vacasa Alabama; Vacasa Arizona; Vacasa Florida; Vacasa Hawaii; Vacasa Louisiana LLC; Vacasa Michigan LLC; Vacasa Montana; Vacasa Nevada LLC; Vacasa New Hampshire LLC; Vacasa New Mexico LLC; Vacasa New York; Vacasa Pennsylvania LLC; Vacasa Tennessee; Vacasa South Carolina LLC; Vacasa Resort Rentals of Hilton Head Island LLC; Vacasa Virginia LLC; Vacasa Wisconsin LLC.