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Holiday hires in Key West

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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 September ($496). Conversely, the most expensive month to stay in Key West is October ($1,082).

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

The cheapest day to stay in Key West is Thursday ($686). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,448.

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

Save money by booking a vacation rental at least 55 days before your trip to Key West. The lowest price found when booking 55 days ahead was $321 per night.

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Cheapest holiday rentals in Key West, Florida

Discover affordable stays in Key West that provide a quality experience without breaking the bank. Hotels in Key West can be found for as low as $332 per night. There is currently one property in Key West that can be booked for this price. Colors On White is one of the hotels that can be booked for the lowest price in Key West. Price data was last updated on 11 March 2026
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.
Colors On White
Colors On White

Colors On White

Key West, FL, United States
0.9 km from city centre
Air conditioning
$332
Avg. per night
View Deal
Pescado Penthouse
Pescado Penthouse

Pescado Penthouse

Key West, FL, United States
0.7 km from city centre
Air conditioning
$1,856
Avg. per night
View Deal
Southernmost Sanctuary All
Southernmost Sanctuary All

Southernmost Sanctuary All

Key West, FL, United States
0.9 km from city centre
Air conditioning
$3,150
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 1,900 hotels in Key West and price data was last updated on 11 March 2026. The average price for a hotel in Key West is $688/night.
Seashell Motel
Seashell Motel

Seashell Motel

718 South Street, Key West, FL, United States
1.0 km from city centre
Free Wi-Fi
Parking
$360
Avg. per night
View Deal
Seascape Tropical Inn
Seascape Tropical Inn

Seascape Tropical Inn

420 Olivia Street, Key West, FL, United States
0.4 km from city centre
Free Wi-Fi
Air conditioning
$421
Avg. per night
View Deal
The Southernmost Inn-Adults Only
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West, FL, United States
0.8 km from city centre
Free Wi-Fi
Air conditioning
$465
Avg. per night
View Deal
Douglas House
Douglas House

Douglas House

419 Amelia Street, Key West, FL, United States
0.6 km from city centre
Free Wi-Fi
Air conditioning
$389
Avg. per night
View Deal

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 11 March 2026.
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 11 March 2026.

  • How much does a holiday rental in Key West cost?

    $688 per night is how much a holiday rental in Key West costs, on average. $178 per night was the cheapest price recently found by our users, though anything for $559 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 January.

  • 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 Key West Villas 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 Opal Key Resort & Marina as it’s currently the most popular Resort rental among our users.

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