A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is AED 882
AED 1,971 total
includes taxes & fees
16 Nov - 17 Nov
Yellow Palm Cottage, Heart of Siesta Key
A deck with a table and chairs, a blue umbrella, and a white fence.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is AED 294
AED 914 total
includes taxes & fees
14 Nov - 15 Nov
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

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 AED 869
AED 1,210 total
includes taxes & fees
10 Nov - 11 Nov
The Inn On Siesta Key
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

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 AED 410
AED 1,293 total
includes taxes & fees
9 Nov - 10 Nov
Beach Tree Cottage,Walk To Beach& Siesta
A patio with a sun lounger, a table with chairs, and an umbrella.

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)
The price is AED 582
AED 1,488 total
includes taxes & fees
11 Nov - 12 Nov
Beach View 100ft To Beach and SPA
A small, single-story building with a gray exterior, a white door, and a window with shutters.

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 AED 184
AED 501 total
includes taxes & fees
13 Nov - 14 Nov
Charming cottage for 2 across warm mineral springs park
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

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 AED 344
AED 889 total
includes taxes & fees
24 Nov - 25 Nov
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A small, single-story building with a porch, surrounded by tropical vegetation.

8. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is AED 648
AED 1,666 total
includes taxes & fees
9 Nov - 10 Nov
BlueDolphin Cottage Walk To Siesta Beach
A two-story house with a green exterior, a blue door, and orange trim.

9. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
United States
Canyon L.
The price is AED 364
AED 749 total
includes taxes & fees
10 Nov - 11 Nov
The "Grouper"
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

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 AED 575
AED 1,446 total
includes taxes & fees
18 Nov - 19 Nov
Lido Key Casita w Pool Steps to the Beach
A residential house with a white fence, a palm tree, and a parked car.

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.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Shared sunbathing deck by the pool, at the resort.

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.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

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 AED 434
AED 1,077 total
includes taxes & fees
5 Dec - 6 Dec
Cozy Private Cottage, Minutes to Anna Maria Island
A small, single-story building with a light beige exterior, a blue door, and a number '229' on the wall.

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 AED 511
AED 1,053 total
includes taxes & fees
9 Nov - 10 Nov
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

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 AED 624
AED 1,345 total
includes taxes & fees
11 Nov - 12 Nov
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A patio with a table set for two, a blue umbrella, and a white fence.

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 AED 575
AED 1,439 total
includes taxes & fees
12 Nov - 13 Nov
Lido Beach Studio with Heated Pool
A modern kitchen with white cabinets, a built-in oven, and a microwave. There is a dining area with a wooden table set for two, blue plates, and wine glasses. A ceiling fan is visible in the living room area.

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.
The price is AED 694
AED 1,444 total
includes taxes & fees
13 Nov - 14 Nov
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

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 AED 727
AED 1,773 total
includes taxes & fees
12 Nov - 13 Nov
Direct Beachfront 2BR Cottage on Casey Key!
A covered patio with a round table set for four, surrounded by wicker chairs.

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 AED 397
AED 1,012 total
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
A covered outdoor seating area with a sofa, a chair, and a coffee table.

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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