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Vacation rentals in Longboat Key

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Travel insights for vacation rentals in Longboat Key

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 324). Conversely, the most expensive month to stay in Longboat Key is April (C$ 3,983).

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

The cheapest day to stay in Longboat Key is Wednesday (C$ 435). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 3,027.

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 C$ 241 per night.
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Cheapest vacation 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 C$ 282 per night. There is currently one property in Longboat Key that can be booked for this price. Little Gull Cottages is one of the hotels that can be booked for the lowest price in Longboat Key. Price data was last updated on 28 August 2025
At the moment, these vacation rentals offer the lowest nightly rate out of those we've come across in Longboat Key. As prices can vary by date, change the dates if you're flexible to compare rates.
Little Gull Cottages
Little Gull Cottages

Little Gull Cottages

Longboat Key, FL, United States
0.4 km from city centre
Air Conditioning
C$ 282
Avg. per night
View Deal
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
C$ 347
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
C$ 535
Avg. per night
View Deal

Other accommodations in Longboat Key

Find the perfect vacation rental for your stay in Longboat Key. There are 990 hotels in Longboat Key and price data was last updated on 28 August 2025. The average price for a hotel in Longboat Key is C$ 661/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
C$ 535
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 28 August 2025.
Scroll through the map to find vacation rentals close to the Longboat Key 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 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 28 August 2025.

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

    Longboat Key vacation rentals are C$ 661/night on average. However, you may find that prices fluctuate depending on the time of year. For example, April is the most expensive month to book a vacation rental in Longboat Key, and December is often the cheapest month to book. Recently, our users found rentals for C$ 172/night - which is currently the cheapest price. Keep in mind that anything C$ 420/night or less is still considered a good deal.

  • What’s the closest vacation rental to Sarasota Bradenton Intl Airport?

    It’s only 22.0 km from Sarasota Bradenton Intl Airport to Haley's at Anna Maria Island Inn (the nearest Longboat Key vacation rental to the airport).

  • Are there Longboat Key vacation rentals with “Pet friendly” listed as an amenity?

    You’re in luck! 1 Longboat Key vacation rental mentions “Pet friendly” under their list of amenities. The Haley's at Anna Maria Island Inn is the most popular vacation rental in Longboat Key that features this amenity.

  • Are there any Resort vacation rentals in Longboat Key?

    Yes, there are 9 Resort vacation rentals in Longboat Key. According to our data, Zota Beach Resort is currently the most popular Resort rental in the city.

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