How much does a holiday rental in Key West cost?

On average, it costs S$ 730 per night for a Key West holiday rental, but S$ 551 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$ 97 per night. If you can, try to avoid booking your rental October (as this is the most expensive month). Booking January (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 Opal Key Resort & Marina.

Key West Holiday Rentals, Apartments & Condos

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 (S$ 426). Conversely, the most expensive month to stay in Key West is March (S$ 1,400).

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

The cheapest day to stay in Key West is Wednesday (S$ 592). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is S$ 1,324.

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 S$ 235 per night.

Find deals

Cheapest holiday rentals in Key West, Florida

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.

Show all 1,827 holiday rentals

Colors On White

Key West, FL, United States

0.9 km from city centre

Air conditioning

S$ 361

Avg. per night

View Deal

Pescado Penthouse

Key West, FL, United States

0.7 km from city centre

Air conditioning

S$ 2,354

Avg. per night

View Deal

Southernmost Sanctuary All

Key West, FL, United States

0.9 km from city centre

Air conditioning

S$ 3,618

Avg. per night

View Deal

Other accommodations in Key West

Show all 1,827 stays

NYAH Key West - Adult Exclusive

420 Margaret Street, Key West, FL, United States

0.5 km from city centre

Free Wi-Fi

Air conditioning

S$ 287

Avg. per night

View Deal

Seashell Motel

718 South Street, Key West, FL, United States

1.0 km from city centre

Free Wi-Fi

Parking

S$ 406

Avg. per night

View Deal

Oceans Edge Key West

5950 Peninsular Avenue, Key West, FL, United States

7.4 km from city centre

Free Wi-Fi

S$ 439

Avg. per night

View Deal

The Laureate Key West

3444 North Roosevelt Boulevard, Key West, FL, United States

4.5 km from city centre

Pool

Parking

S$ 474

Avg. per night

View Deal

Pegasus International Hotel

501 Southard Street, Key West, FL, United States

0.1 km from city centre

Free Wi-Fi

Parking

S$ 476

Avg. per night

View Deal

La Concha Key West, Autograph Collection

430 Duval Street, Key West, FL, United States

0.3 km from city centre

Free Wi-Fi

S$ 621

Avg. per night

View Deal

Southernmost Beach Resort & Guesthouses

1319 Duval Street, Key West, FL, United States

0.9 km from city centre

Free Wi-Fi

Spa

S$ 482

Avg. per night

View Deal

Beachside Resort & Residences

3841 North Roosevelt Boulevard, Key West, FL, United States

5.2 km from city centre

Free Wi-Fi

S$ 554

Avg. per night

View Deal

Where to stay in Key West

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

How much does a holiday rental in Key West cost?
On average, it costs S$ 730 per night for a Key West holiday rental, but S$ 551 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$ 97 per night. If you can, try to avoid booking your rental October (as this is the most expensive month). Booking January (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 Opal Key Resort & Marina.

Find better results for your stay in Key West

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Travel insights for holiday rentals in Key West

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 (S$ 426). Conversely, the most expensive month to stay in Key West is March (S$ 1,400).

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

The cheapest day to stay in Key West is Wednesday (S$ 592). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is S$ 1,324.

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 S$ 235 per night.

Cheapest holiday rentals in Key West, Florida

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.

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 29 January 2026. The average price for a hotel in Key West is S$ 729/night.

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 29 January 2026.

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 29 January 2026.

How much does a holiday rental in Key West cost?

Are there any Resort holiday rentals in Key West?

Find better results for your stay in Key West

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Vacation rentals in Key West

Search and compare Key West, FL holiday rentals from hundreds of travel sites on HotelsCombined and save.

Travel insights for holiday rentals in Key West

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 (S$ 426). Conversely, the most expensive month to stay in Key West is March (S$ 1,400).

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

The cheapest day to stay in Key West is Wednesday (S$ 592). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is S$ 1,324.

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 S$ 235 per night.

Cheapest holiday rentals in Key West, Florida

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.

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 29 January 2026. The average price for a hotel in Key West is S$ 729/night.

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 29 January 2026.

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 29 January 2026.

How much does a holiday rental in Key West cost?

Are there any Resort holiday rentals in Key West?

Find better results for your stay in Key West

Popular holiday destinations in Florida

Find holiday rentals in popular Florida cities that fit your unique needs