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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 August ($697). Conversely, the most expensive month to stay in Key West is December ($2,142).

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

The cheapest day to stay in Key West is Sunday ($597). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $1,085.

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 $396 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 $378 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 18 August 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
$378
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
$2,041
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 2,475 hotels in Key West and price data was last updated on 18 August 2025. The average price for a hotel in Key West is $823/night.
La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

430 Duval Street, Key West, FL, United States
0.3 km from city centre
Free Wi-Fi
$402
Avg. per night
View Deal
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL, United States
1.3 km from city centre
$486
Avg. per night
View Deal
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
$363
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
$278
Avg. per night
View Deal
Southwinds Motel
Southwinds Motel

Southwinds Motel

1321 Simonton Street, Key West, FL, United States
0.9 km from city centre
$247
Avg. per night
View Deal
Blue Marlin Motel
Blue Marlin Motel

Blue Marlin Motel

1320 Simonton Street, Key West, FL, United States
0.9 km from city centre
Free Wi-Fi
$217
Avg. per night
View Deal
The Grand Guesthouse
The Grand Guesthouse

The Grand Guesthouse

1116 Grinnell Street, Key West, FL, United States
0.9 km from city centre
Free Wi-Fi
Parking
$250
Avg. per night
View Deal
New Orleans House
New Orleans House

New Orleans House

724 Duval Street, Key West, FL, United States
0.2 km from city centre
Free Wi-Fi
$344
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 18 August 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 18 August 2025.

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

    $823 per night is how much a holiday rental in Key West costs, on average. $124 per night was the cheapest price recently found by our users, though anything for $566 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 February, 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 Casa Marina Key West, Curio Collection by Hilton 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 $77 and Hotels Under $154. Discover hotel discounts now and make your hotel reservation today.