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Vacation rentals 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 ($353). Conversely, the most expensive month to stay in Key West is October ($769).

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

The cheapest day to stay in Key West is Thursday ($488). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,029.

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 $228 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 $235 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 13 March 2026
At the moment, these vacation rentals offer the lowest nightly rate out of those we've come across in Key West. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
Colors On White
Colors On White

Colors On White

Key West, FL, United States
0.9 km from city centre
Air conditioning
$235
Avg. per night
View Deal
Pescado Penthouse
Pescado Penthouse

Pescado Penthouse

Key West, FL, United States
0.7 km from city centre
Air conditioning
$1,264
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
$2,213
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 1,908 hotels in Key West and price data was last updated on 13 March 2026. The average price for a hotel in Key West is $489/night.
Oceans Edge Key West
Oceans Edge Key West

Oceans Edge Key West

5950 Peninsular Avenue, Key West, FL, United States
7.4 km from city centre
Free Wi-Fi
$306
Avg. per night
View Deal
Pegasus International Hotel
Pegasus International Hotel

Pegasus International Hotel

501 Southard Street, Key West, FL, United States
0.1 km from city centre
Free Wi-Fi
Parking
$266
Avg. per night
View Deal
Eden House
Eden House

Eden House

1015 Fleming Street, Key West, FL, United States
0.7 km from city centre
Free Wi-Fi
Parking
$250
Avg. per night
View Deal
Duval Inn
Duval Inn

Duval Inn

511 Angela Street, Key West, FL, United States
0.1 km from city centre
Free Wi-Fi
Parking
$295
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
$299
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
$331
Avg. per night
View Deal
NYAH Key West - Adult Exclusive
NYAH Key West - Adult Exclusive

NYAH Key West - Adult Exclusive

420 Margaret Street, Key West, FL, United States
0.5 km from city centre
Free Wi-Fi
Air conditioning
$257
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 13 March 2026.
Scroll through the map to find vacation rentals close to the Key West neighborhood(s) you plan on visiting. You can find more information on a particular vacation rental within the map by clicking on its name.

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 13 March 2026.

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

    The average cost for a holiday rental in Key West is $489/night. A good holiday rental deal in Key West would be for $397/night or less. The cheapest rental deal found recently by our users was $126/night. If you’re flexible with your travel dates, then try to avoid booking October, the most expensive month of the year. Booking January is the cheapest month to book a holiday rental in Key West.

  • What part of Key West is best to stay in?

    Old Town North of Truman is the best part of Key West to stay in based on our user data. Out of all our users who looked at Key West holiday rentals, 100% of them looked for stays in the Old Town North of Truman neighbourhood in the last year. The Key West Villas happens to be the most popular holiday rental in the Old Town North of Truman neighbourhood of Key West.

  • Are there any Resort holiday rentals in Key West?

    Yes, there are 25 Resort holiday rentals in Key West. According to our data, Opal Key Resort & Marina is currently the most popular Resort rental in the city.

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