Vacation rentals in Longboat Key
Search and compare Longboat Key, FL holiday rentals from hundreds of travel sites on HotelsCombined and save.
Longboat Key, United States
7 May — 8 May2
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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 (S$ 315). Conversely, the most expensive month to stay in Longboat Key is October (S$ 928).
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$ 497). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 799.
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$ 229 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 S$ 546 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 30 April 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.
Show all 838 holiday rentals
Holmes Beach, FL, United States
3.2 km from city centre
Air conditioning
S$ 546
Avg. per night
S$ 555
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 30 April 2025. The average price for a hotel in Longboat Key is S$ 491/night.
Show all 838 stays
Longboat Key, FL, United States
2.9 km from city centre
Air conditioning
S$ 523
Avg. per night
4711 Gulf of Mexico Drive, Longboat Key, FL, United States
1.8 km from city centre
Parking
S$ 471
Avg. per night
4141 Gulf of Mexico Drive, Longboat Key, FL, United States
3.0 km from city centre
Free Wi-Fi
Parking
S$ 365
Avg. per night
S$ 374
Avg. per night