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Featured Cottages in Legacy Trail and around

The Lookout, 1 King Bedroom 1 Bath | Balcony view

"Great place to stay! "

"Right on the beach, quiet, clean and absolutely perfect for a couple's getaway. Andrew was great to work and went out of his way to make our stay perfect!"

includes taxes & fees

10 Sept - 11 Sept

"We loved this little cottage and will absolutely go back in the future. Thank you so much for a wonderful retreat. "

includes taxes & fees

13 Sept - 14 Sept

"We enjoyed our stay so much! Just right for us with short walks to the Beach and Bay, peaceful back porch and comfy beds. It is a beautiful and clean house in the trees. Evan is a helpful host with great communication. We hope to go back again. "

"Great little place to stay in a convenient location! Would definitely stay there again. "

includes taxes & fees

10 Sept - 11 Sept

"My family and I thoroughly enjoyed our stay! We will definitely rent again in the future. It’s in a great location and just steps away from the beautiful ocean! "

"We thoroughly enjoyed our time at this lovely home. It was located in near multiple excellent restaurants and rental stores and was within walking distance to Bean Beach. The place was clean and had all the amenities needed to make our stay perfect and memorable. "

"Wonderful experience and area."

"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "

includes taxes & fees

10 Sept - 11 Sept

"Very private and far enough for peaceful setting "

"We enjoyed all the extra touches the owner provided, the place was well stocked with items to improve our stay, such as beach items, bathroom items, spices and kitchen supplies.The house and pool were both clean and well maintained.The location to the beach and the village were great."

"Wonderful location for a peaceful getaway "

"We had a family of four stay here. Perfect size for what we needed and close to everything. It was our 2nd time on the Island and this place was perfect. "