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Vacation rentals in Siesta Key

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Travel insights for vacation rentals in Siesta Key

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Siesta Key.

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 ($223). Conversely, the most expensive month to stay in Siesta Key is January ($416).

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

The cheapest day to stay in Siesta Key is Sunday ($306). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $363.

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 vacation 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 July 28, 2025
These Siesta Key properties charge the lowest price per night of those we've come across. As prices can vary by date, change the dates if you're flexible to compare rates.
Siesta Key Beachside Villas
Siesta Key Beachside Villas

Siesta Key Beachside Villas

Siesta Key, FL, United States
1.4 mi 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
0.5 mi from city centre
Air Conditioning
Parking
$256
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
0.5 mi 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
0.5 mi from city centre
Air Conditioning
$295
Avg. per night
View Deal

Other accommodations in Siesta Key

Find the perfect vacation rental for your stay in Siesta Key. There are 3,340 hotels in Siesta Key and price data was last updated on July 28, 2025. The average price for a hotel in Siesta Key is $326/night.
Turtle Beach Resort
Turtle Beach Resort

Turtle Beach Resort

9049 Midnight Pass Road, Siesta Key, FL, United States
4.0 mi from city centre
Free Wi-Fi
Parking
$231
Avg. per night
View Deal
Captiva Beach Resort
Captiva Beach Resort

Captiva Beach Resort

6772 Sara Sea Circle, Siesta Key, FL, United States
1.6 mi from city centre
Free Wi-Fi
Parking
$219
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
0.9 mi from city centre
Free Wi-Fi
Parking
$224
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
1.6 mi from city centre
Free Wi-Fi
$260
Avg. per night
View Deal
Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management

Crescent Street Villas by Beachside Management

Siesta Key, FL, United States
1.7 mi from city centre
Air Conditioning
$281
Avg. per night
View Deal

Where to stay in Siesta Key

Explore different neighborhoods and areas within Siesta Key to find the perfect location for your stay. Map data was last updated on July 28, 2025.
Scroll through the map to find vacation rentals close to the Siesta Key neighborhood(s) you plan on visiting. You can find more information on a particular vacation rental within the map by clicking on its name.

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 July 28, 2025.

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

    $326 per night is how much a vacation rental in Siesta Key costs, on average. $82 per night was the cheapest price recently found by our users, though anything for $259 per night or less is a good deal. Keep in mind that Siesta Key vacation rental prices fluctuate throughout the year: the most expensive month to book is July, and the cheapest time to book is November.

  • What’s the closest vacation rental to Sarasota Bradenton Intl Airport?

    It’s only 10.3 mi from Sarasota Bradenton Intl Airport to Bianco Sands by Beachside Management (the nearest Siesta Key vacation rental to the airport).

  • Are there any Resort vacation rentals in Siesta Key?

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

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