486 Properties in Siesta Key, Florida, United States of America. September 6, 2026 through September 7, 2026

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Siesta Key Beach

Point of Rocks

St. Boniface Episcopal Church Labyrinth

Safe Harbor Siesta Key

Jim Neville Marine Preserve

Turtle Beach

Crescent Beach

Shell Beach

Irma Beach

Siesta Key Farmers Market

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Siesta Key

Siesta Key Village

Aloha Kai

Bay Isle

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Bailey Hall

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Enjoy the season with activities like ice skating, snowmobiling, or sledding.

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30th Anniversary Sale: Members save up to 30%

For a limited time, save on select hotels & vacation rentals. Book by October 7.

A narrow concrete pathway flanked by lush tropical plants, leading to a wooden gate.

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

VIP Access

Captiva Beach Resort

South Village

Pool
Kitchen

9.09.0 out of 10

Wonderfulwonderful

1,307 reviews(1,307 reviews)

$194 nightly

The current price is $236 total

$236 total

Total with taxes and fees

We have 1 left at this price

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A swimming pool with blue lounge chairs and palm trees.

A beach with several beach chairs and umbrellas, a small table, and a few people relaxing.

Siesta Key Beach Resort and Suites

Siesta Key Village

Pool
Hot tub

9.29.2 out of 10

Wonderfulwonderful

1,183 reviews(1,183 reviews)

Sale $29 off

$146 nightly

The current price is $220 total

$220 total

Total with taxes and fees

We have 1 left at this price

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A pathway lined with palm trees and tropical plants, leading to a building with a white facade.

A pool area with a waterfall feature, lounge chairs, and palm trees.

Tropical Beach Resorts

South Village

Pool
Kitchen

Fully refundable

9.49.4 out of 10

Exceptionalexceptional

5,882 reviews(5,882 reviews)

$169 nightly

The current price is $217 total

$217 total

Total with taxes and fees

We have 1 left at this price

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30th Anniversary Sale: Members save up to 30%

Photo gallery for Captiva Beach Resort

Captiva Beach Resort

Photo gallery for Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

Photo gallery for Tropical Beach Resorts

Tropical Beach Resorts