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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 ($710). Conversely, the most expensive month to stay in Key West is April ($1,683).

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

The cheapest day to stay in Key West is Thursday ($560). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,360.

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 $389 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 $333 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 12 September 2025
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.
Key West Villas
Key West Villas

Key West Villas

Key West, FL, United States
0.1 km from city centre
Air conditioning
$333
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
$2,019
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 2,472 hotels in Key West and price data was last updated on 12 September 2025. The average price for a hotel in Key West is $808/night.
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
$137
Avg. per night
View Deal
Ambrosia Key West
Ambrosia Key West

Ambrosia Key West

622 Fleming Street, Key West, FL, United States
0.3 km from city centre
Free Wi-Fi
Air conditioning
$259
Avg. per night
View Deal
Duval House
Duval House

Duval House

815 Duval Street, Key West, FL, United States
0.3 km from city centre
Free Wi-Fi
Air conditioning
$175
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
$166
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
$267
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 12 September 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 12 September 2025.

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

    $809 per night is how much a holiday rental in Key West costs, on average. $103 per night was the cheapest price recently found by our users, though anything for $552 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 May, and the cheapest time to book is August.

  • 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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Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $75 and Hotels Under $151. Discover hotel discounts now and make your hotel reservation today.