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Vacation rentals in Siesta Key

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Travel insights for holiday rentals in Siesta Key

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

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

The cheapest month to book a vacation rental in Siesta Key is September ($230). Conversely, the most expensive month to stay in Siesta Key is December ($547).

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

The cheapest day to stay in Siesta Key is Sunday ($260). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $359.

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

Save money by booking a vacation rental at least 77 days before your trip to Siesta Key. The lowest price found when booking 77 days ahead was $209 per night.
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Cheapest holiday rentals in Siesta Key, Florida

Discover affordable stays in Siesta Key that provide a quality experience without breaking the bank. Hotels in Siesta Key can be found for as low as $255 per night. There is currently one property in Siesta Key that can be booked for this price. Siesta Key Beachside Villas is one of the hotels that can be booked for the lowest price in Siesta Key. Price data was last updated on 31 July 2025
For those on a budget, these are the cheapest vacation rentals available in Siesta Key for the selected dates. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Siesta Key Beachside Villas
Siesta Key Beachside Villas

Siesta Key Beachside Villas

Siesta Key, FL, United States
2.3 km from city centre
Air conditioning
$255
Avg. per night
View Deal
Villa 38 - Aloha Kai Vacation Villas
Villa 38 - Aloha Kai Vacation Villas

Villa 38 - Aloha Kai Vacation Villas

Siesta Key, FL, United States
0.9 km from city centre
Air conditioning
Parking
$258
Avg. per night
View Deal
Villa 33 - Aloha Kai Vacation Villas
Villa 33 - Aloha Kai Vacation Villas

Villa 33 - Aloha Kai Vacation Villas

Siesta Key, FL, United States
0.9 km from city centre
Air conditioning
Parking
$285
Avg. per night
View Deal
Villa 41 - Aloha Kai Vacation Villas
Villa 41 - Aloha Kai Vacation Villas

Villa 41 - Aloha Kai Vacation Villas

Siesta Key, FL, United States
0.9 km from city centre
Air conditioning
$295
Avg. per night
View Deal

Other accommodations in Siesta Key

Find the perfect holiday rental for your stay in Siesta Key. There are 3,343 hotels in Siesta Key and price data was last updated on 31 July 2025. The average price for a hotel in Siesta Key is $335/night.
Siesta Key Beachside Villas
Siesta Key Beachside Villas

Siesta Key Beachside Villas

Siesta Key, FL, United States
2.3 km from city centre
Air conditioning
$255
Avg. per night
View Deal
Beachside Studio Located Across From Main Beach And Half Mile To Village
Beachside Studio Located Across From Main Beach And Half Mile To Village

Beachside Studio Located Across From Main Beach And Half Mile To Village

Siesta Key, FL, United States
1.0 km from city centre
Air conditioning
$177
Avg. per night
View Deal
Siesta Palms By the Beach
Siesta Palms By the Beach

Siesta Palms By the Beach

1017 Point of Rocks Rd, Siesta Key, FL, United States
2.6 km from city centre
Free Wi-Fi
$252
Avg. per night
View Deal
Avenida De Cortez 5210
Avenida De Cortez 5210

Avenida De Cortez 5210

Siesta Key, FL, United States
1.9 km from city centre
Air conditioning
$334
Avg. per night
View Deal

Where to stay in Siesta Key

Explore different neighbourhoods and areas within Siesta Key to find the perfect location for your stay. Map data was last updated on 31 July 2025.
Use the map to find vacation rentals in Siesta Key that are close to the points of interest you'll be frequenting. Clicking a property's name will unlock more information and allow you to book that particular vacation rental.

Facts about staying in Siesta Key

Find useful tips and insights about staying in Siesta Key to help you make the most of your experience. FAQs were last updated on 31 July 2025.

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

    The average cost for a holiday rental in Siesta Key is $336/night. A good holiday rental deal in Siesta Key would be for $276/night or less. The cheapest rental deal found recently by our users was $69/night. If you’re flexible with your travel dates, then try to avoid booking July, the most expensive month of the year. Booking November is the cheapest month to book a holiday rental in Siesta Key.

  • Are there any Resort holiday rentals in Siesta Key?

    Yes, there are 9 Resort holiday rentals in Siesta Key. According to our data, Turtle Beach Resort is currently the most popular Resort rental in the city.

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