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 September ($184). Conversely, the most expensive month to stay in Longboat Key is October ($542).
What is the cheapest day to stay in a vacation rental in Longboat Key?
The cheapest day to stay in Longboat Key is Sunday ($290). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $467.
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 $175 per night.
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 $417 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 2 May 2025
For those on a budget, these are the cheapest vacation rentals available in Longboat Key for the selected dates. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
Show all 838 holiday rentals
Holmes Beach, FL, United States
3.2 km from city centre
Air conditioning
$417
Avg. per night
$424
Avg. per night
Other accommodations in Longboat Key
Find the perfect holiday rental for your stay in Longboat Key. There are 838 hotels in Longboat Key and price data was last updated on 2 May 2025. The average price for a hotel in Longboat Key is $375/night.
Show all 838 stays
Longboat Key, FL, United States
2.9 km from city centre
Air conditioning
$400
Avg. per night
4711 Gulf of Mexico Drive, Longboat Key, FL, United States
1.8 km from city centre
Parking
$360
Avg. per night
4141 Gulf of Mexico Drive, Longboat Key, FL, United States
3.0 km from city centre
Free Wi-Fi
Parking
$279
Avg. per night
4235 Gulf of Mexico Drive, Longboat Key, FL, United States
2.9 km from city centre
Free Wi-Fi
Air conditioning
$389
Avg. per night