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Holiday 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 August ($589). Conversely, the most expensive month to stay in Key West is March ($1,297).

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

The cheapest day to stay in Key West is Wednesday ($898). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $1,655.

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

Save money by booking a vacation rental at least 51 days before your trip to Key West. The lowest price found when booking 51 days ahead was $294 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 $495 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 23 January 2026
For those on a budget, these are the cheapest holiday rentals available in Key West for the selected dates. 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
$495
Avg. per night
View Deal
Banana's Foster Guesthouse
Banana's Foster Guesthouse

Banana's Foster Guesthouse

537 Caroline St, Key West, FL, United States
0.5 km from city centre
Free Wi-Fi
$713
Avg. per night
View Deal
Pescado Penthouse
Pescado Penthouse

Pescado Penthouse

Key West, FL, United States
0.7 km from city centre
Air conditioning
$3,201
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
$4,763
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 1,827 hotels in Key West and price data was last updated on 23 January 2026. The average price for a hotel in Key West is $924/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
$794
Avg. per night
View Deal
Southernmost Beach Resort & Guesthouses
Southernmost Beach Resort & Guesthouses

Southernmost Beach Resort & Guesthouses

1319 Duval Street, Key West, FL, United States
0.9 km from city centre
Free Wi-Fi
Spa
$704
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
$698
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
$384
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 23 January 2026.
Use the map to find holiday rentals in Key West that are close to the points of interest you'll be frequenting. 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 23 January 2026.

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

    $925/night is a typical cost for a holiday rental in Key West throughout the year. Rental prices do vary though, and you’ll find that October is the most expensive month to book, and January is the cheapest month to book. HotelsCombined users recently found Key West holiday rentals for as low as $85/night. In general, any Key West rental for $748 or less is a good deal.

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

    Old Town North of Truman is the most popular area of Key West to stay in. In the past year, 100% of HotelsCombined users looking for Key West holiday rentals searched within Old Town North of Truman. Based on user data, the Colors On White is one of the most popular holiday rentals in Old Town North of Truman.

  • Are there any Resort holiday rentals in Key West?

    At the moment, there are 25 properties listed as a Resort holiday rental in Key West. A popular Resort in Key West amongst our users is Opal Key Resort & Marina.

Find better results for your stay in Key West

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