How much does a holiday rental in Key West cost?

$768 per night is how much a holiday rental in Key West costs, on average. $126 per night was the cheapest price recently found by our users, though anything for $587 per night or less is a good deal. Keep in mind that Key West holiday rental prices fluctuate throughout the year: the most expensive month to book is October, and the cheapest time to book is September.

What part of Key West is best to stay in?

Old Town North of Truman is the best part of the city to stay in if you’re looking for a holiday rental in Key West. The Old Town Suites is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Key West, 100% of HotelsCombined users searched for rentals in Old Town North of Truman in the past 12 months, making it a popular choice.

Are there any Resort holiday rentals in Key West?

If you’re looking to book a Resort holiday rental in Key West, then you have 25 to choose from. We recommend looking at Casa Marina Key West, Curio Collection by Hilton as it’s currently the most popular Resort rental among our users.

Holiday hires in Key West

Search and compare Key West, FL holiday rentals from hundreds of travel sites on HotelsCombined and save.

Travel insights for holiday rentals in Key West

Use these up-to-date, data-driven insights about booking a holiday rental in Key West including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Key West?

The cheapest month to book a vacation rental in Key West is May ($830). Conversely, the most expensive month to stay in Key West is October ($1,934).

What is the cheapest day to stay in a vacation rental in Key West?

The cheapest day to stay in Key West is Thursday ($866). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $1,137.

How far ahead should you book a vacation rental in Key West?

Save money by booking a vacation rental at least 1 day before your trip to Key West. The lowest price found when booking 1 day ahead was $456 per night.

Cheapest holiday rentals in Key West, Florida

Out of the holiday rentals in Key West we've come across, these properties are priced the lowest. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 2,126 hotels in Key West and price data was last updated on 6 June 2025. The average price for a hotel in Key West is $767/night.

Where to stay in Key West

Explore different neighbourhoods and areas within Key West to find the perfect location for your stay. Map data was last updated on 6 June 2025.

Scroll to and zoom in on the areas in Key West you plan on visiting to find nearby properties. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday rental.

Facts about staying in Key West

Find useful tips and insights about staying in Key West to help you make the most of your experience. FAQs were last updated on 6 June 2025.

How much does a holiday rental in Key West cost?

What part of Key West is best to stay in?

Are there any Resort holiday rentals in Key West?

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