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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 KeySiesta Key Village
The price is AU$676
includes taxes & fees
9 Nov - 10 Nov
2. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Perfect Getaway – Lovely One Bedroom cottage House – Near BeachesNokomis
The price is AU$357
includes taxes & fees
14 Nov - 15 Nov
3. The Inn On Siesta Key
The Inn On Siesta KeySiesta 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...
Karen Jean
The price is AU$484
includes taxes & fees
10 Nov - 11 Nov
4. Beach Tree Cottage,Walk To Beach& Siesta
Beach Tree Cottage,Walk To Beach& SiestaSiesta Key Village
The price is AU$469
includes taxes & fees
11 Nov - 12 Nov
5. Beach View 100ft To Beach and SPA
Beach View 100ft To Beach and SPASiesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is AU$552
includes taxes & fees
11 Nov - 12 Nov
6. Charming cottage for 2 across warm mineral springs park
Charming cottage for 2 across warm mineral springs parkWarm Mineral Springs
9.0 out of 10, Wonderful, (29 reviews)
"Host responded quicklyWould stay again"
VIKTOR M.
The price is AU$200
includes taxes & fees
13 Nov - 14 Nov
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
The price is AU$354
includes taxes & fees
24 Nov - 25 Nov
8. BlueDolphin Cottage Walk To Siesta Beach
BlueDolphin Cottage Walk To Siesta BeachSiesta Key Village
The price is AU$661
includes taxes & fees
9 Nov - 10 Nov
9. The "Grouper"
The "Grouper"Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
Canyon L.
The price is AU$301
includes taxes & fees
11 Nov - 12 Nov
10. Lido Key Casita w Pool Steps to the Beach
Lido Key Casita w Pool Steps to the BeachLido Key
10.0 out of 10, Exceptional, (2 reviews)
"Alex was very quick to reply to my questions. Room was exactly as pictured!"
Felecia P.
The price is AU$563
includes taxes & fees
18 Nov - 19 Nov
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."
Clarissa S.
12. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bedSiesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
Russ H.
13. Cozy Private Cottage, Minutes to Anna Maria Island
Cozy Private Cottage, Minutes to Anna Maria IslandBradenton
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
Ismael
The price is AU$353
includes taxes & fees
10 Nov - 11 Nov
14. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beachNokomis
9.2 out of 10, Wonderful, (34 reviews)
"Great location"
Susan C.
The price is AU$416
includes taxes & fees
9 Nov - 10 Nov
15. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Escape near Siesta Key with Hot Tub, BBQ, and Fire pitSarasota
8.4 out of 10, Very good, (10 reviews)
"Very close drive to the beach! Nice place to stay!"
Rocio S.
The price is AU$527
includes taxes & fees
11 Nov - 12 Nov
16. Lido Beach Studio with Heated Pool
Lido Beach Studio with Heated PoolLido Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful place!!"
Lorraine B.
The price is AU$563
includes taxes & fees
26 Nov - 27 Nov
17. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and VillageSarasota
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!"
Tracie B.
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."
Tom K.
The price is AU$708
includes taxes & fees
12 Nov - 13 Nov
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 FriendlyEnglewood Central
10.0 out of 10, Exceptional, (16 reviews)
"Great stay for our family of 5!"
Shawn G.
The price is AU$399
includes taxes & fees
9 Nov - 10 Nov
20. Nook Cottage Across street from beach and Heated Pool
Nook Cottage Across street from beach and Heated PoolSiesta 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!"
Derek N.
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.
Learn more about Legacy Trail
Venture to Siesta Key Beach and Lido Beach—just two of the top sights around Legacy Trail, a city also notable for its beaches and wildlife.
