Best Cottages Legacy Trail in 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Legacy Trail cottages

A yellow house with a porch, a mailbox, and a number 5306 on the door.

1. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

₹37,460 total

includes taxes & fees

9 Nov - 10 Nov

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

2. The Inn On Siesta Key

Siesta Key

"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...