A wooden pathway surrounded by dense greenery and trees.

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Our top choices for Legacy Trail cottages

1. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is €417
includes taxes & fees
9 Nov - 10 Nov
Yellow Palm Cottage, Heart of Siesta Key

2. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is €221
includes taxes & fees
14 Nov - 15 Nov
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

3. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (213 reviews)
"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...
United States
Karen Jean
The price is €298
includes taxes & fees
10 Nov - 11 Nov
The Inn On Siesta Key

4. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is €316
includes taxes & fees
9 Nov - 10 Nov
Beach Tree Cottage,Walk To Beach& Siesta

5. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
Beach View 100ft To Beach and SPA

6. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (29 reviews)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
The price is €125
includes taxes & fees
13 Nov - 14 Nov
Charming cottage for 2 across warm mineral springs park

7. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

8. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is €407
includes taxes & fees
9 Nov - 10 Nov
BlueDolphin Cottage Walk To Siesta Beach

9. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
United States
Canyon L.
The price is €188
includes taxes & fees
10 Nov - 11 Nov
The "Grouper"

10. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (2 reviews)
"Alex was very quick to reply to my questions. Room was exactly as pictured!"
United States
Felecia P.
The price is €351
includes taxes & fees
18 Nov - 19 Nov
Lido Key Casita w Pool Steps to the Beach

11. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.8 out of 10, Exceptional, (91 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is €277
includes taxes & fees
10 Nov - 11 Nov
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

12. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is €303
includes taxes & fees
10 Nov - 11 Nov
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

13. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
The price is €222
includes taxes & fees
10 Nov - 11 Nov
Cozy Private Cottage, Minutes to Anna Maria Island

14. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
Nokomis
9.2 out of 10, Wonderful, (34 reviews)
"Great location"
United States
Susan C.
The price is €259
includes taxes & fees
9 Nov - 10 Nov
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

15. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"Very close drive to the beach! Nice place to stay!"
United States
Rocio S.
The price is €324
includes taxes & fees
11 Nov - 12 Nov
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

16. Lido Beach Studio with Heated Pool

Lido Beach Studio with Heated Pool
Lido Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful place!!"
United States
Lorraine B.
The price is €356
includes taxes & fees
12 Nov - 13 Nov
Lido Beach Studio with Heated Pool

17. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

18. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (86 reviews)
"Beach view was amazing. Very private. Minimal other folks on the beach. Loved the covered deck for that brief summer rain shower."
United States
Tom K.
The price is €440
includes taxes & fees
12 Nov - 13 Nov
Direct Beachfront 2BR Cottage on Casey Key!

19. Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
10.0 out of 10, Exceptional, (16 reviews)
"Great stay for our family of 5!"
United States
Shawn G.
The price is €251
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

20. Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
Nook Cottage Across street from beach and Heated Pool
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

Legacy Trail Cottages information

Number of reviews
749
Accommodation
0 Cottages
Lowest Price
€125
Highest Price
€440

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