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Vacation rentals in Longboat Key

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Travel insights for holiday rentals in Longboat Key

Use these up-to-date, data-driven insights about booking a holiday rental in Longboat Key including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Longboat Key?

The cheapest month to book a vacation rental in Longboat Key is January (S$ 255). Conversely, the most expensive month to stay in Longboat Key is April (S$ 4,671).

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

The cheapest day to stay in Longboat Key is Sunday (S$ 459). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is S$ 2,622.

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

Save money by booking a vacation rental at least 83 days before your trip to Longboat Key. The lowest price found when booking 83 days ahead was S$ 224 per night.
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Cheapest holiday rentals in Longboat Key, Florida

Discover affordable stays in Longboat Key that provide a quality experience without breaking the bank. Hotels in Longboat Key can be found for as low as S$ 265 per night. There is currently one property in Longboat Key that can be booked for this price. Haley's at Anna Maria Island Inn is one of the hotels that can be booked for the lowest price in Longboat Key. Price data was last updated on 16 September 2025
At the moment, these vacation rentals offer the lowest nightly rate out of those we've come across in Longboat Key. If you have the flexibility, change the dates selected to compare prices.
Haley's at Anna Maria Island Inn
Haley's at Anna Maria Island Inn

Haley's at Anna Maria Island Inn

Holmes Beach, FL, United States
3.2 km from city centre
Air conditioning
S$ 265
Avg. per night
View Deal
Little Gull Cottages
Little Gull Cottages

Little Gull Cottages

Longboat Key, FL, United States
0.4 km from city centre
Air conditioning
S$ 288
Avg. per night
View Deal
Turtle Crawl Inn
Turtle Crawl Inn

Turtle Crawl Inn

4235 Gulf of Mexico Drive, Longboat Key, FL, United States
2.9 km from city centre
Free Wi-Fi
Air conditioning
S$ 498
Avg. per night
View Deal

Other accommodations in Longboat Key

Find the perfect holiday rental for your stay in Longboat Key. There are 984 hotels in Longboat Key and price data was last updated on 16 September 2025. The average price for a hotel in Longboat Key is S$ 743/night.
Turtle Crawl Inn
Turtle Crawl Inn

Turtle Crawl Inn

4235 Gulf of Mexico Drive, Longboat Key, FL, United States
2.9 km from city centre
Free Wi-Fi
Air conditioning
S$ 498
Avg. per night
View Deal
Zota Beach Resort
Zota Beach Resort

Zota Beach Resort

4711 Gulf of Mexico Drive, Longboat Key, FL, United States
1.8 km from city centre
Parking
S$ 361
Avg. per night
View Deal
The Resort At Longboat Key Club
The Resort At Longboat Key Club

The Resort At Longboat Key Club

220 Sands Point Road, Longboat Key, FL, United States
11.3 km from city centre
Free Wi-Fi
S$ 450
Avg. per night
View Deal
Sea Club I
Sea Club I

Sea Club I

4141 Gulf of Mexico Drive, Longboat Key, FL, United States
3.0 km from city centre
Free Wi-Fi
Parking
S$ 305
Avg. per night
View Deal

Where to stay in Longboat Key

Explore different neighbourhoods and areas within Longboat Key to find the perfect location for your stay. Map data was last updated on 16 September 2025.
Scroll to and zoom in on the areas in Longboat Key you plan on visiting to find nearby properties. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

Facts about staying in Longboat Key

Find useful tips and insights about staying in Longboat Key to help you make the most of your experience. FAQs were last updated on 16 September 2025.

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

    On average, it costs S$ 744 per night for a Longboat Key holiday rental, but S$ 430 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Longboat Key was for S$ 191 per night. If you can, try to avoid booking your rental April (as this is the most expensive month). Booking April (the cheapest month) may end up saving you money.

  • Are there any Resort holiday rentals in Longboat Key?

    There are 9 holiday rentals in Longboat Key that fall under the Resort category, the most popular is Zota Beach Resort.

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