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Compare 21 Cottages in Longboat Key with updated reviews, rates, and availability.

FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3/29 - 4/5 2025
FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3/29 - 4/5 2025
10.0 out of 10, Exceptional, (2)

Longboat Key Cottage: Extended Stays Welcome!
Longboat Key Cottage: Extended Stays Welcome!

Charming Bayside 1BR Cottage
Charming Bayside 1BR Cottage

2BR Cottage Bayside Time for Relaxation
2BR Cottage Bayside Time for Relaxation

2BR Gulf Front, Feel the Gulf Breezes on the Porch
2BR Gulf Front, Feel the Gulf Breezes on the Porch

2BR Cottage Bay Views Bayside
2BR Cottage Bay Views Bayside

2BR Cottage Bayside Close to the Pool
2BR Cottage Bayside Close to the Pool
10.0 out of 10, Exceptional, (1)

2BR Cottage Gulf Side of Property, Resort Amenities
2BR Cottage Gulf Side of Property, Resort Amenities
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Longboat Key

Sea Club I Beach Resort
Sea Club I Beach Resort
9.0 out of 10, Wonderful, (302)

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
9.8 out of 10, Exceptional, (137)

Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
9.6 out of 10, Exceptional, (17)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Longboat Key hotels
Recent reviews of Longboat Key hotels

Silver Sands on the Sea!
5/5 Excellent
Perfect Vacation
"This was a perfect vacation for us. The property was beautiful, right on the beach, and we could walk to some great bars and restaurants. The owner was very kind and communicated often to see if we needed anything. We would definitely stay here again!"
A verified traveler from Hilliard, Ohio stayed at Silver Sands on the Sea!
Posted 2 days ago