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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 (S$ 412). Conversely, the most expensive month to stay in Key West is December (S$ 1,358).

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

The cheapest day to stay in Key West is Tuesday (S$ 458). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 709.

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

Save money by booking a vacation rental at least 1 day before your trip to Key West. The lowest price found when booking 1 day ahead was S$ 380 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 S$ 317 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 30 July 2025
These are the lowest prices we've found on vacation rentals in Key West at the moment. If you have the flexibility, change the dates selected to compare prices.
Key West Villas
Key West Villas

Key West Villas

Key West, FL, United States
0.1 km from city centre
Air conditioning
S$ 317
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
S$ 1,290
Avg. per night
View Deal

Other accommodations in Key West

Find the perfect holiday rental for your stay in Key West. There are 2,458 hotels in Key West and price data was last updated on 30 July 2025. The average price for a hotel in Key West is S$ 678/night.
Seascape Tropical Inn
Seascape Tropical Inn

Seascape Tropical Inn

420 Olivia Street, Key West, FL, United States
0.3 km from city centre
Free Wi-Fi
Air conditioning
S$ 270
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
S$ 178
Avg. per night
View Deal
Key West Villas
Key West Villas

Key West Villas

Key West, FL, United States
0.1 km from city centre
Air conditioning
S$ 317
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
S$ 161
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
S$ 286
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
S$ 253
Avg. per night
View Deal
Hampton Inn Key West
Hampton Inn Key West

Hampton Inn Key West

3755 South Roosevelt Boulevard, Key West, FL, United States
5.2 km from city centre
Free Wi-Fi
Parking
S$ 288
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
S$ 198
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 30 July 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 30 July 2025.

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

    On average, it costs S$ 679 per night for a Key West holiday rental, but S$ 447 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Key West was for S$ 109 per night. If you can, try to avoid booking your rental May (as this is the most expensive month). Booking June (the cheapest month) may end up saving you money.

  • Are there any Resort holiday rentals in Key West?

    There are 25 holiday rentals in Key West that fall under the Resort category, the most popular is Casa Marina Key West, Curio Collection by Hilton.

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