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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 ($312). Conversely, the most expensive month to stay in Key West is April ($740).

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

The cheapest day to stay in Key West is Thursday ($246). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $598.

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

Save money by booking a vacation rental at least 5 days before your trip to Key West. The lowest price found when booking 5 days ahead was $258 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 $221 per night. There is currently one property in Key West that can be booked for this price. Key West Villas is one of the hotels that can be booked for the lowest price in Key West. Price data was last updated on 13 September 2025
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.
Key West Villas
Key West Villas

Key West Villas

Key West, FL, United States
0.1 km from city centre
Air conditioning
$221
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
$1,339
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 2,466 hotels in Key West and price data was last updated on 13 September 2025. The average price for a hotel in Key West is $536/night.
Southernmost Beach Resort
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West, FL, United States
0.9 km from city centre
Free Wi-Fi
Spa
$187
Avg. per night
View Deal
Beachside Resort & Residences
Beachside Resort & Residences

Beachside Resort & Residences

3841 North Roosevelt Boulevard, Key West, FL, United States
5.2 km from city centre
Free Wi-Fi
$168
Avg. per night
View Deal
Ocean Key Resort & Spa, a Noble House Resort
Ocean Key Resort & Spa, a Noble House Resort

Ocean Key Resort & Spa, a Noble House Resort

0 Duval Street, Key West, FL, United States
0.9 km from city centre
Free Wi-Fi
$260
Avg. per night
View Deal
Seashell Motel and International Hostel
Seashell Motel and International Hostel

Seashell Motel and International Hostel

718 South Street, Key West, FL, United States
1.0 km from city centre
Free Wi-Fi
Parking
$110
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
Parking
$145
Avg. per night
View Deal
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
$185
Avg. per night
View Deal
The Laureate Key West
The Laureate Key West

The Laureate Key West

3444 North Roosevelt Boulevard, Key West, FL, United States
4.5 km from city centre
Pool
Parking
$193
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
$191
Avg. per night
View Deal
Duval Inn - Key West
Duval Inn - Key West

Duval Inn - Key West

511 Angela Street, Key West, FL, United States
0.1 km from city centre
Free Wi-Fi
Parking
$191
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 September 2025.
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 September 2025.

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

    The average cost for a holiday rental in Key West is $536/night. A good holiday rental deal in Key West would be for $366/night or less. The cheapest rental deal found recently by our users was $68/night. If you’re flexible with your travel dates, then try to avoid booking May, the most expensive month of the year. Booking August 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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