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Holiday hires 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 ($512). Conversely, the most expensive month to stay in Siesta Key is March ($942).

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

The cheapest day to stay in Siesta Key is Sunday ($714). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $4,531.

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 $316 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 $382 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 25 July 2025
Out of the holiday rentals in Siesta Key we've come across, these properties are priced the lowest. 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
$382
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
$387
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
$431
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
$446
Avg. per night
View Deal

Other accommodations in Siesta Key

Find the perfect holiday rental for your stay in Siesta Key. There are 3,340 hotels in Siesta Key and price data was last updated on 25 July 2025. The average price for a hotel in Siesta Key is $488/night.
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
$493
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
$401
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
$350
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
$331
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
$333
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 25 July 2025.
Utilise the map to find properties close to the Siesta Key area(s) or attractions 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 25 July 2025.

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

    $489 per night is how much a holiday rental in Siesta Key costs, on average. $124 per night was the cheapest price recently found by our users, though anything for $389 per night or less is a good deal. Keep in mind that Siesta Key holiday rental prices fluctuate throughout the year: the most expensive month to book is July, and the cheapest time to book is November.

  • Are there any Resort holiday rentals in Siesta Key?

    If you’re looking to book a Resort holiday rental in Siesta Key, then you have 9 to choose from. We recommend looking at Golden Host Resort - Sarasota 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 $151. Discover hotel discounts now and make your hotel reservation today.