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Browse Select Legacy Trail Cottages

Our top choices for Legacy Trail cottages

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.4 out of 10, Exceptional, (98)
"We had an amazing long weekend here! The owner was very accommodating, the place was exactly as described, clean and quiet, and the beach leaves us lost for words!"
The price is €397
includes taxes & fees
26 Sept - 27 Sept
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (63)
"We loved this little cottage and will absolutely go back in the future. Thank you so much for a wonderful retreat. "
The price is €418
includes taxes & fees
17 Sept - 18 Sept
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"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. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

The "Grouper"

9.4 out of 10, Exceptional, (36)
"Great location."
The price is €184
includes taxes & fees
16 Sept - 17 Sept
The "Grouper"

Tropical Paradise On The Beach Permit VRC17-000168

9.2 out of 10, Wonderful, (139)
"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! "
Tropical Paradise On The Beach Permit VRC17-000168

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (286)
"Clean and quiet and the best location for a weekend getaway! "
Charming cottage in quiet area, close to beach & bay.

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (94)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"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. "
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "
Country Cottage Home

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (24)
"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

Cozy Beach Cottage

9.4 out of 10, Exceptional, (21)
"Wonderful location for a peaceful getaway "
Cozy Beach Cottage

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (13)
"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. "
Anna Maria Cottage with Golf Cart

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (127)
"We enjoyed our stay and will definitely come back. Very clean! Comfy beds . Well stocked "
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

The Cottage by Anna Maria Island

9.0 out of 10, Wonderful, (14)
"Great host ,nice property. We had a problem with the shower, but the host had it fixed almost immediately. Would definitely stay here again."
The Cottage by Anna Maria Island

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

9.6 out of 10, Exceptional, (120)
"Beautiful quiet stay on the water. I would definitely stay here again!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

2 Mi to Anna Maria Island: Newly Built Home!

3.0 star property
2 Mi to Anna Maria Island: Newly Built Home!

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.0 out of 10, Wonderful, (9)
"Great location. Very clean and well maintained. I would come back "
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

Blue Isle Oasis: Adorable, updated 2 bedroom cottage

9.4 out of 10, Exceptional, (3)
"Lovely renovation! Great access to restaurants, beach, and dog park!!"
Blue Isle Oasis: Adorable, updated 2 bedroom cottage

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (137)
"Perfect cottage getaway right on the beach. Will be back again "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
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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Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Find out more about Legacy Trail

Legacy Trail Cottages information

Number of reviews
1,544
Accommodation
57 Cottages
Lowest Price
€184
Highest Price
€418