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Holiday 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 October ($585). Conversely, the most expensive month to stay in Siesta Key is December ($2,360).

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

The cheapest day to stay in Siesta Key is Thursday ($780). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $879.

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

Save money by booking a vacation rental at least 70 days before your trip to Siesta Key. The lowest price found when booking 70 days ahead was $327 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 $339 per night. There is currently one property in Siesta Key that can be booked for this price. Villa 41 - Aloha Kai Vacation Villas is one of the hotels that can be booked for the lowest price in Siesta Key. Price data was last updated on 7 September 2025
Currently, these are the lowest-priced holiday rentals in Siesta Key we've come across for the dates selected. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
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
$339
Avg. per night
View Deal
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
$417
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
$497
Avg. per night
View Deal
Bianco Sands by Beachside Management
Bianco Sands by Beachside Management

Bianco Sands by Beachside Management

Siesta Key, FL, United States
2.7 km from city centre
Air conditioning
$499
Avg. per night
View Deal

Other accommodations in Siesta Key

Find the perfect holiday rental for your stay in Siesta Key. There are 3,338 hotels in Siesta Key and price data was last updated on 7 September 2025. The average price for a hotel in Siesta Key is $646/night.
Siesta Palms By The Beach
Siesta Palms By The Beach

Siesta Palms By The Beach

1017 Point Of Rocks Road, Siesta Key, FL, United States
2.6 km from city centre
Free Wi-Fi
Parking
$363
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
$536
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
$287
Avg. per night
View Deal
Turtle Beach Resort
Turtle Beach Resort

Turtle Beach Resort

9049 Midnight Pass Road, Siesta Key, FL, United States
6.4 km from city centre
Free Wi-Fi
Parking
$403
Avg. per night
View Deal
Captiva Beach Resort
Captiva Beach Resort

Captiva Beach Resort

6772 Sara Sea Circle, Siesta Key, FL, United States
2.5 km from city centre
Free Wi-Fi
Parking
$346
Avg. per night
View Deal
The Ringling Beach House
The Ringling Beach House

The Ringling Beach House

523 Beach Road, Siesta Key, FL, United States
1.4 km from city centre
Free Wi-Fi
Parking
$396
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 7 September 2025.
Scroll through the map to find holiday rentals close to the Siesta Key neighbourhood(s) you plan on visiting. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

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 7 September 2025.

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

    $647/night is a typical cost for a holiday rental in Siesta Key throughout the year. Rental prices do vary though, and you’ll find that February is the most expensive month to book, and October is the cheapest month to book. HotelsCombined users recently found Siesta Key holiday rentals for as low as $132/night. In general, any Siesta Key rental for $525 or less is a good deal.

  • Are there any Resort holiday rentals in Siesta Key?

    At the moment, there are 9 properties listed as a Resort holiday rental in Siesta Key. A popular Resort in Siesta Key amongst our users is Captiva Beach Resort.

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