A wooden pathway surrounded by dense greenery and trees.

Search Legacy Trail Cottage Rentals from CA $194

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Legacy Trail cottages

1. 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 CA $252
CA $607 total
includes taxes & fees
Nov 15 - Nov 16
Beach View 100ft To Beach and SPA

2. 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 $355 total
includes taxes & fees
Nov 16 - Nov 17
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

3. 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 $344
CA $767 total
includes taxes & fees
Nov 15 - Nov 16
Yellow Palm Cottage, Heart of Siesta Key

4. 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, (30 reviews)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
The price is CA $71
CA $194 total
includes taxes & fees
Nov 14 - Nov 15
Charming cottage for 2 across warm mineral springs park

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 $134
CA $345 total
includes taxes & fees
Dec 2 - Dec 3
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

6. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
United States
Canyon L.
The price is CA $141
CA $292 total
includes taxes & fees
Nov 15 - Nov 16
The "Grouper"

7. 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 $112
CA $351 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Private Cottage, Minutes to Anna Maria Island

8. 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 $269
CA $560 total
includes taxes & fees
Nov 16 - Nov 17
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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, (2 reviews)
"Alex was very quick to reply to my questions. Room was exactly as pictured!"
United States
Felecia P.
The price is CA $223
CA $575 total
includes taxes & fees
Nov 18 - Nov 19
Lido Key Casita w Pool Steps to the Beach

10. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is CA $313
CA $732 total
includes taxes & fees
Nov 16 - Nov 17
PinkMango Cottage Steps to Beach&Village

11. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is CA $282
CA $682 total
includes taxes & fees
Nov 15 - Nov 16
BlueDolphin Cottage Walk To Siesta Beach

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 CA $178
CA $457 total
includes taxes & fees
Nov 15 - Nov 16
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

13. 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 CA $223
CA $576 total
includes taxes & fees
Nov 26 - Nov 27
Lido Beach Studio with Heated Pool

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 CA $198
CA $409 total
includes taxes & fees
Nov 16 - Nov 17
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

15. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.6 out of 10, Exceptional, (137 reviews)
"Cute little cottage right on the beach. Doesn’t get any better than that."
United States
kelly h.
The price is CA $282
CA $686 total
includes taxes & fees
Nov 16 - Nov 17
Casey Key Beachfront Escape: Charming 1BR Cottage

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.6 out of 10, Excellent, (11 reviews)
"Very close drive to the beach! Nice place to stay!"
United States
Rocio S.
The price is CA $242
CA $522 total
includes taxes & fees
Nov 24 - Nov 25
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

17. 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, (24 reviews)
"Location was optimum for us. "
United States
James K.
The price is CA $203
CA $553 total
includes taxes & fees
Nov 20 - Nov 21
NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly

18. 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
9.8 out of 10, Exceptional, (17 reviews)
"Great stay for our family of 5!"
United States
Shawn G.
The price is CA $154
CA $393 total
includes taxes & fees
Nov 14 - Nov 15
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

19. 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 $249
CA $676 total
includes taxes & fees
Dec 1 - Dec 2
Home < 1-mi Walk to Warm Mineral Springs Park!

20. 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 $694 total
includes taxes & fees
Dec 14 - Dec 15
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Legacy Trail Cottages information

Number of reviews
543
Accommodation
0 Cottages
Lowest Price
CA $194
Highest Price
CA $767

Explore a world of travel with Expedia