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Holiday hires 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 ($359). Conversely, the most expensive month to stay in Longboat Key is April ($6,570).

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

The cheapest day to stay in Longboat Key is Sunday ($646). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $3,688.

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 $266 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 $315 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 9 September 2025
These are the lowest prices we've found on holiday rentals in Longboat Key at the moment. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Little Gull Cottages
Little Gull Cottages

Little Gull Cottages

Longboat Key, FL, United States
0.4 km from city centre
Air conditioning
$315
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
$383
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
$591
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 9 September 2025.
Whether you're visiting Longboat Key for leisure or business, utilise the map to find holiday rentals close to your ideal location. Users can click on a holiday 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 9 September 2025.

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

    $882 per night is how much a holiday rental in Longboat Key costs, on average. $226 per night was the cheapest price recently found by our users, though anything for $510 per night or less is a good deal. Keep in mind that Longboat Key holiday rental prices fluctuate throughout the year: the most expensive month to book is April, and the cheapest time to book is April.

  • Are there any Resort holiday rentals in Longboat Key?

    If you’re looking to book a Resort holiday rental in Longboat Key, then you have 9 to choose from. We recommend looking at Zota Beach Resort as it’s currently the most popular Resort rental among our users.

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Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $152. Discover hotel discounts now and make your hotel reservation today.