Siesta Key Cottage Rentals

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Booking Insights
Recommended by KAYAK

Best Siesta Key cottage rentals

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$121 - $355$355 - $589$589 - $823$823 - $1,057$1,057+ per night

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Most recommended cottage rentals in Siesta Key

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Inviting Sarasota Cottage 5 Mi to Beach Access! - Sarasota - Kitchen
Inviting Sarasota Cottage 5 Mi to Beach Access!
Sarasota, FL
8.0Very good(10)
Cottage
Free Wi-Fi
$164+
Check availability
Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village - Siesta Key - Beach
Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village
Siesta Key, FL
9.3Wonderful(26)
Cottage
Free Wi-Fi
$424+
Check availability
5 Min walk to Beach & Village, Private Pool,On the Canal - Siesta Key - Kitchen
5 Min walk to Beach & Village, Private Pool,On the Canal
Siesta Key, FL
9.7Wonderful(24)
Cottage
Free Wi-Fi
Pool
$457+
Check availability
Flip Flop Cottages - Siesta Key - Patio
Flip Flop Cottages
Siesta Key, FL
7.8Good(34)
Cottage
Free Wi-Fi
Pet friendly
$476+
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Location. 3 bedroom cottage block from beach and two blocks from Siesta Village - Siesta Key - Living room
Location. 3 bedroom cottage block from beach and two blocks from Siesta Village
Siesta Key, FL
9.4Wonderful(17)
Cottage
$632+
Check availability
Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village - Siesta Key - Bedroom
Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village
Siesta Key, FL
9.6Wonderful(43)
Cottage
$368+
Check availability
Nook Cottage Across street from beach and Heated Pool - Siesta Key - Pool
Nook Cottage Across street from beach and Heated Pool
Siesta Key, FL
10Wonderful(4)
Cottage
$751+
Check availability
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai! - Siesta Key - Balcony
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
Siesta Key, FL
9.2Wonderful(5)
Cottage
Free Wi-Fi
Pool
$552+
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Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed - Siesta Key - Living room
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key, FL
9.0Wonderful(4)
Cottage
$490+
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Key West Style Beach Cottage Just Steps From #1 Siesta Key Beach! - Siesta Key - Patio
Key West Style Beach Cottage Just Steps From #1 Siesta Key Beach!
Siesta Key, FL
10Wonderful(31)
Cottage
Free Wi-Fi
$313+
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Fiddle Fig Cottage - Siesta Key
Fiddle Fig Cottage
Siesta Key, FL
7.7Good(13)
Cottage
$426+
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Aloha Kai - 14A 1 Bedroom 1 Bathroom Villa - Siesta Key
Aloha Kai - 14A 1 Bedroom 1 Bathroom Villa
Siesta Key, FL
Cottage
Free Wi-Fi
$346+
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Aloha Kai - 31 2 Bedrooms 1 Bathroom Villa - Siesta Key
Aloha Kai - 31 2 Bedrooms 1 Bathroom Villa
Siesta Key, FL
Cottage
Free Wi-Fi
$362+
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Cottage 15 Ss 1 Bedroom 1 Bathroom Cottage - Siesta Key
Cottage 15 Ss 1 Bedroom 1 Bathroom Cottage
Siesta Key, FL
Cottage
Free Wi-Fi
$390+
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Avenida de Mayo Home 436 3 Bedrooms 2 Bathrooms Home - Siesta Key
Avenida de Mayo Home 436 3 Bedrooms 2 Bathrooms Home
Siesta Key, FL
Cottage
Free Wi-Fi
$399+
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315 Canal Rd 2 Bedrooms 2 Bathrooms Duplex - Siesta Key
315 Canal Rd 2 Bedrooms 2 Bathrooms Duplex
Siesta Key, FL
Cottage
Free Wi-Fi
$314+
Check availability
Booking Insights

KAYAK’s Insights for cottages in Siesta Key

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Siesta Key with confidence.

What is the cheapest day of the week to book a cottage in Siesta Key?

Tuesday offers the lowest rates in Siesta Key, with an average nightly price of $190/night. The highest prices are found on Sunday, with average rates at $2,108/night.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
March
$842
$781
Cheapest month to stay with an average 74% drop in price.
Most expensive month to stay with an average 256% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Siesta Key vacation rental deals

  • For the cheapest cottage rental in Siesta Key, try to visit during the low season and outside of main travel peaks. The cheapest rates can be found in May and December.
  • The cheapest night of the week to rent a cottage in Siesta Key is Tuesday. On the other hand, the most expensive is Sunday.

Where to stay in Siesta Key?

Our map will help you find the perfect place to stay in Siesta Key by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Siesta Key