A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Legacy Trail cottages

An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

1. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is CA $187
CA $491 total
includes taxes & fees
Nov 3 - Nov 4
Beach Tree Cottage,Walk To Beach& Siesta
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 CA $125
CA $366 total
includes taxes & fees
Nov 17 - Nov 18
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A hot tub surrounded by a wooden fence, with lounge chairs and an umbrella in the background.

3. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is CA $238
CA $550 total
includes taxes & fees
Nov 1 - Nov 2
PinkMango Cottage Steps to Beach&Village
A two-story house with a green exterior, a blue door, and orange trim.

4. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (78 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $139
CA $299 total
includes taxes & fees
Oct 30 - Oct 31
The "Grouper"
A small, single-story building with a gray exterior, a white door, and a window with shutters.

5. 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 CA $77
CA $210 total
includes taxes & fees
Nov 13 - Nov 14
Charming cottage for 2 across warm mineral springs park
A patio with a sun lounger, a table with chairs, and an umbrella.

6. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is CA $240
CA $553 total
includes taxes & fees
Nov 1 - Nov 2
Beach View 100ft To Beach and SPA
A small, single-story building with a porch, surrounded by tropical vegetation.

7. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is CA $248
CA $560 total
includes taxes & fees
Nov 2 - Nov 3
BlueDolphin Cottage Walk To Siesta Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

8. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is CA $208
CA $576 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Lido Studio by Beach & St Armand's
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

9. 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, (1 review)
The price is CA $208
CA $576 total
includes taxes & fees
Nov 18 - Nov 19
Lido Key Casita w Pool Steps to the Beach
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

10. 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)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
The price is CA $238
CA $536 total
includes taxes & fees
Oct 31 - Nov 1
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

11. 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 CA $131
CA $350 total
includes taxes & fees
Nov 24 - Nov 25
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A yellow house with a porch, a mailbox, and a number 5306 on the door.

12. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is CA $305
CA $626 total
includes taxes & fees
Nov 1 - Nov 2
Yellow Palm Cottage, Heart of Siesta Key
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 CA $133
CA $394 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Private Cottage, Minutes to Anna Maria Island
Shared sunbathing deck by the pool, at the resort.

14. 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 CA $175
CA $491 total
includes taxes & fees
Nov 10 - Nov 11
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A small, single-story building with a light beige exterior, a blue door, and a number '229' on the wall.

15. 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 CA $194
CA $415 total
includes taxes & fees
Nov 8 - Nov 9
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
A covered patio with a round table set for four, surrounded by wicker chairs.

16. 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 CA $120
CA $363 total
includes taxes & fees
Oct 31 - Nov 1
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
A residential house with a white fence, a palm tree, and a parked car.

17. 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 CA $139
CA $424 total
includes taxes & fees
Nov 3 - Nov 4
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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)
"Great vacation!!"
United States
Dominic C.
The price is CA $277
CA $709 total
includes taxes & fees
Oct 31 - Nov 1
Direct Beachfront 2BR Cottage on Casey Key!
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.

19. 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 CA $223
CA $498 total
includes taxes & fees
Nov 4 - Nov 5
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A patio with two blue lounge chairs, a potted plant, and a gravel area.

20. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is CA $245
CA $470 total
includes taxes & fees
Nov 17 - Nov 18
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
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
531
Accommodation
0 Cottages
Lowest Price
CA $210
Highest Price
CA $709

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