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Holiday hires in Key West

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Travel insights for holiday rentals in Key West

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Key West.

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

The cheapest day to stay in Key West is Monday ($310). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $693.

How early should you book a vacation rental in Key West?

Based on vacation rental prices in Key West found by KAYAK users over the last 12 months.

Book at least 51 days before your stay begins to get the best price for your Key West vacation rental.

Find deals

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 $144 per night. There is currently one property in Key West that can be booked for this price. NYAH Key West - Adult Exclusive is one of the hotels that can be booked for the lowest price in Key West. Price data was last updated on 6 August 2026
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.
NYAH Key West - Adult Exclusive
NYAH Key West - Adult Exclusive

NYAH Key West - Adult Exclusive

Key West, FL, United States
0.5 km from city centre
Air conditioning
$144
Avg. per night
View Deal
Heron House - Adult Only
Heron House - Adult Only

Heron House - Adult Only

Key West, FL, United States
0.1 km from city centre
Air conditioning
$155
Avg. per night
View Deal
The Independent Inn
The Independent Inn

The Independent Inn

412 Frances Street, Key West, FL, United States
0.8 km from city centre
Free Wi-Fi
Parking
$170
Avg. per night
View Deal
Colors On White
Colors On White

Colors On White

Key West, FL, United States
0.9 km from city centre
Air conditioning
$232
Avg. per night
View Deal
Weatherstation Inn
Weatherstation Inn

Weatherstation Inn

57 Front Street, Key West, FL, United States
0.6 km from city centre
Free Wi-Fi
Air conditioning
$250
Avg. per night
View Deal
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Key West, FL, United States
0.4 km from city centre
Air conditioning
Free Wi-Fi
$541
Avg. per night
View Deal
Pescado Penthouse
Pescado Penthouse

Pescado Penthouse

Key West, FL, United States
0.7 km from city centre
Air conditioning
$851
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 1,913 hotels in Key West and price data was last updated on 6 August 2026. The average price for a hotel in Key West is .
Seascape Tropical Inn - Adult Exclusive
Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive

420 Olivia Street, Key West, FL, United States
0.4 km from city centre
Free Wi-Fi
Air conditioning
$256
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
$165
Avg. per night
View Deal
Fitch Lodge - Key West Historic Inns
Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

1030 Eaton Street, Key West, FL, United States
0.8 km from city centre
Free Wi-Fi
Air conditioning
$163
Avg. per night
View Deal
Hilton Key West Resort & Marina
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

5950 Peninsular Avenue, Key West, FL, United States
7.3 km from city centre
Free Wi-Fi
$263
Avg. per night
View Deal
Opal Key Resort & Marina
Opal Key Resort & Marina

Opal Key Resort & Marina

245 Front Street, Key West, FL, United States
0.8 km from city centre
Free Wi-Fi
$463
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
$196
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 6 August 2026.
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 6 August 2026.

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

    $725 per night is how much a holiday rental in Key West costs, on average. $98 per night was the cheapest price recently found by our users, though anything for $583 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 November, and the cheapest time to book is May.

  • What is the best Key West holiday rental?

    The best holiday rental in Key West is The Independent Inn, according to our user data. 71 users from HotelsCombined gave the The Independent Inn a 8.0/10 rating.

  • What’s the closest holiday rental to Key West Airport?

    If you’re looking to stay close to Key West Airport for your trip to Key West, then consider booking a The Independent Inn holiday rental. This holiday apartment is just 3.8 km away from the Key West airport.

  • 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 NYAH Key West - Adult Exclusive 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.

  • What’s the most popular holiday rental in Key West near Duval Street?

    NYAH Key West - Adult Exclusive is the most popular Key West holiday rental near Duval Street (the city’s most popular landmark). It’s a 0.7 km trip from NYAH Key West - Adult Exclusive to Duval Street. While there may be other holiday rentals near Duval Street, NYAH Key West - Adult Exclusive received high marks (7.6/10) from 3,817 users.

  • Are there Key West holiday rentals with “Pool” listed as an amenity?

    Yes, there are 2 holiday rentals in Key West with “Pool” listed as an amenity, the most popular being the NYAH Key West - Adult Exclusive rental based on user data.

  • 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 33 to choose from. We recommend looking at Hilton Key West Resort & Marina as it’s currently the most popular Resort rental among our users.

See more FAQs

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