A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Legacy Trail cottages

A pair of stacked front-loading washing machines in a commercial setting.

1. 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 $194
CA $504 total
includes taxes & fees
Oct 8 - Oct 9
Beach View 100ft To Beach and SPA
A small, single-story building with a gray exterior, a white door, and a window with shutters.

2. 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)
"We were enjoying our stay."
United States
Inna K.
The price is CA $57
CA $190 total
includes taxes & fees
Oct 6 - Oct 7
Charming cottage for 2 across warm mineral springs park
A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is CA $114
CA $362 total
includes taxes & fees
Oct 6 - Oct 7
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

4. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
"5 Stars: This cozy studio was exactly what we were looking for. Alexander was pleasant and friendly, the check in/check out process was easy. The location was fabulous- perhaps slightly too far to walk to St.Armand’s , but a quick ride on the rentable VEO bikes/scooters. The accommodations were clean, and beachy. We did not have an opportunity to use the pool, so I do have any objective comments for the pool. If we are in the area again, we would definitely stay here again!"
United States
lisa o.
The price is CA $219
CA $597 total
includes taxes & fees
Oct 10 - Oct 11
Coastal Studio, Walk to St Armand's or Lido Beach
A single-story house with a blue exterior, a front door, and a small porch area.

5. 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 $148
CA $379 total
includes taxes & fees
Oct 12 - Oct 13
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A two-story house with a green exterior, a blue door, and orange trim.

6. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $141
CA $302 total
includes taxes & fees
Oct 8 - Oct 9
The "Grouper"
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

7. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
The price is CA $77
CA $329 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Private Cottage, Minutes to Anna Maria Island
Shared sunbathing deck by the pool, at the resort.

8. 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 $157
CA $471 total
includes taxes & fees
Oct 6 - Oct 7
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is CA $296
CA $695 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Lido Studio by Beach & St Armand's
A residential house with a white fence, a palm tree, and a parked car.

10. 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
9.6 out of 10, Exceptional, (90 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 $141
CA $433 total
includes taxes & fees
Oct 6 - Oct 7
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A covered patio with a round table set for four, surrounded by wicker chairs.

11. 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)
"Very clean house, nice place to stay"
United States
Linda G.
The price is CA $111
CA $353 total
includes taxes & fees
Oct 24 - Oct 25
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
A residential house with a garage, a front door, and a small front yard.

12. Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is CA $214
CA $636 total
includes taxes & fees
Oct 9 - Oct 10
Home < 1-mi Walk to Warm Mineral Springs Park!
A beachfront property with a house, palm trees, and a view of the ocean.

13. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful gulf view."
United States
Audrey B.
The price is CA $425
CA $860 total
includes taxes & fees
Oct 17 - Oct 18
Casey Key Beachfront Escape: Charming 1BR Cottage
An outdoor swimming pool with a wooden deck and a ladder.

14. NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly

NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly
Myakka City
10.0 out of 10, Exceptional, (23 reviews)
"Location was optimum for us. "
United States
James K.
The price is CA $162
CA $452 total
includes taxes & fees
Oct 7 - Oct 8
NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly
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)
"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 $341
CA $655 total
includes taxes & fees
Oct 8 - Oct 9
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

16. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $569
CA $1,019 total
includes taxes & fees
Oct 7 - Oct 8
Siesta Heron 6 / Sunset
A patio with a table set for two, a blue umbrella, and a white fence.

17. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is CA $256
CA $643 total
includes taxes & fees
Oct 16 - Oct 17
Studio by Lido Beach w heated pool
A single-story house with a front porch, a red door, and a pathway leading to the entrance.

18. New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee

New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
Myakka City
9.8 out of 10, Exceptional, (8 reviews)
"Was perfect spot for the purpose of our trip!"
United States
Cheryl L.
The price is CA $285
CA $611 total
includes taxes & fees
Oct 6 - Oct 7
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
A covered outdoor area with a gravel ground, a covered seating area with chairs, and a building in the background.

19. Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Manasota Key
10.0 out of 10, Exceptional, (7 reviews)
"If you are looking for a quaint getaway in a quiet part of Manasota key, this is it. While you are close enough walk or bike to the beach and all the restaurant/bars, it’s just far enough away from all the congestion. The cottage was beautifully decorated, clean & updated. Truly a great host, they were responsive and provided more items to use than any other VRBO we’ve stayed at! "
United States
Brooke T.
The price is CA $292
CA $726 total
includes taxes & fees
Oct 7 - Oct 8
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

20. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
The price is CA $288
CA $591 total
includes taxes & fees
Oct 26 - Oct 27
Bridge Street Beach House | Wi-Fi | Center of All
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
269
Accommodation
0 Cottages
Lowest Price
CA $190
Highest Price
CA $1,019

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