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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 (S$ 308). Conversely, the most expensive month to stay in Siesta Key is February (S$ 582).

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

The cheapest day to stay in Siesta Key is Sunday (S$ 259). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 411.

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 S$ 227 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 S$ 230 per night. There is currently one property in Siesta Key that can be booked for this price. Siesta Heron Suites & Villas is one of the hotels that can be booked for the lowest price in Siesta Key. Price data was last updated on 30 October 2025
Out of the vacation 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 Heron Suites & Villas
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Key, FL, United States
4.8 km from city centre
Air conditioning
S$ 230
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
S$ 294
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
S$ 400
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
S$ 430
Avg. per night
View Deal

Other accommodations in Siesta Key

Find the perfect holiday rental for your stay in Siesta Key. There are 2,427 hotels in Siesta Key and price data was last updated on 30 October 2025. The average price for a hotel in Siesta Key is S$ 412/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
S$ 399
Avg. per night
View Deal
Siesta Heron Suites & Villas
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Key, FL, United States
4.8 km from city centre
Air conditioning
S$ 230
Avg. per night
View Deal
Siesta Key Inn
Siesta Key Inn

Siesta Key Inn

1125 Point of Rocks Rd, Siesta Key, FL, United States
2.6 km from city centre
Free Wi-Fi
Air conditioning
S$ 322
Avg. per night
View Deal
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
S$ 304
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
S$ 294
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 30 October 2025.
Utilize the map to find properties close to the Siesta Key area(s) or attractions you plan on visiting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 30 October 2025.

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

    On average, it costs S$ 413 per night for a Siesta Key holiday rental, but S$ 347 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Siesta Key was for S$ 80 per night. If you can, try to avoid booking your rental March (as this is the most expensive month). Booking October (the cheapest month) may end up saving you money.

  • Are there any Resort holiday rentals in Siesta Key?

    There are 9 holiday rentals in Siesta Key that fall under the Resort category, the most popular is Captiva Beach Resort (open private beach access).

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