A wooden pathway surrounded by dense greenery and trees.

Holiday Homes in Legacy Trail

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Our top choices for Legacy Trail holiday homes

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is AU$456
includes taxes & fees
9 Nov - 10 Nov
Siesta Heron Suites & Villas

2. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is AU$334
includes taxes & fees
17 Nov - 18 Nov
The Dolphin

3. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"The place was super cute, clean, quiet, cozy, and in a great location. The host was very communicative and sweet. Definitely a great stay, 10/10 recommend!"
United States
Sierra B.
The price is AU$394
includes taxes & fees
8 Nov - 9 Nov
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

4. Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (29 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is AU$360
includes taxes & fees
9 Nov - 10 Nov
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

5. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is AU$378
includes taxes & fees
9 Nov - 10 Nov
[lounge like locals] walk to siesta beach +bikes

6. Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is AU$296
includes taxes & fees
9 Nov - 10 Nov
Nestled in North Port. Updated 2 Bed / 1 Bath.

7. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is AU$330
includes taxes & fees
18 Nov - 19 Nov
Lakeview Bradenton Rental Near Beaches & IMG

8. Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is AU$389
includes taxes & fees
1 Dec - 2 Dec
Old Floridian cottage in Historic Gulf Village

9. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (177 reviews)
"Great downtown location! We enjoyed our stay!"
United States
Diane M.
The price is AU$411
includes taxes & fees
8 Nov - 9 Nov
The Hideaways at Point Pleasant (Palm Side)

10. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Ridge Wood Heights
9.4 out of 10, Exceptional, (129 reviews)
"Beautiful home, perfect location! Would come back again. Thank you!!! "
United States
Joe V.
The price is AU$445
includes taxes & fees
22 Nov - 23 Nov
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

11. Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Sabal Harbour
10.0 out of 10, Exceptional, (35 reviews)
"Great location! I loved the sunsets on the back patio!"
United States
Megan R.
The price is AU$458
includes taxes & fees
9 Nov - 10 Nov
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

12. Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.

Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.
Whitfield Estates
9.0 out of 10, Wonderful, (26 reviews)
"Great clean adorable place"
United States
Joann G.
The price is AU$416
includes taxes & fees
8 Nov - 9 Nov
Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.

13. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (6 reviews)
"The host was so nice I’ll be staying there again!"
United States
Melissa
The price is AU$375
includes taxes & fees
22 Nov - 23 Nov
Charming 2-bedroom house in Englewood with WiFi and AC

14. The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (182 reviews)
"Great location and wonderful place to stay."
United States
Theresa H.
The price is AU$403
includes taxes & fees
22 Nov - 23 Nov
The Hideaways at Point Pleasant (Pine Side)

15. Modern Coastal Charm • Near AMI Beach-IMG Academy

Modern Coastal Charm • Near AMI Beach-IMG Academy
Bradenton
10.0 out of 10, Exceptional, (41 reviews)
"Everything was Perfect! Highly recommend, will Defiantly stay again "
United States
Melanie L.
The price is AU$427
includes taxes & fees
12 Nov - 13 Nov
Modern Coastal Charm • Near AMI Beach-IMG Academy

16. Nautical Nook

Nautical Nook
Englewood
9.8 out of 10, Exceptional, (16 reviews)
"It was super clean and the host was great"
United States
Dolores
The price is AU$354
includes taxes & fees
19 Nov - 20 Nov
Nautical Nook

17. 1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
River District
10.0 out of 10, Exceptional, (84 reviews)
"Lovely cottage!"
United States
Steve M.
The price is AU$478
includes taxes & fees
10 Nov - 11 Nov
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

18. Pet-Friendly Stay 4miles to Beach

Pet-Friendly Stay 4miles to Beach
Venice Gardens
10.0 out of 10, Exceptional, (7 reviews)
"I loved this home and will definitely go back if I'm in the area. It was a nice quiet neighborhood, very close to lots of places. The place was updated very well & so spacious. The owner was super responsive. I wish I stayed longer just to enjoy the cute yard and sitting areas."
United States
Jessica
The price is AU$527
includes taxes & fees
8 Nov - 9 Nov
Pet-Friendly Stay 4miles to Beach

19. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (223 reviews)
"Nice stay perfect location"
United States
tom f.
The price is AU$668
includes taxes & fees
9 Nov - 10 Nov
Siesta beach....one and only

20. Romantic studio • Bikes included • Near the beach.

Romantic studio • Bikes included • Near the beach.
Bradenton
9.8 out of 10, Exceptional, (28 reviews)
"We enjoyed staying here for our anniversary vacation"
United States
Toby L.
The price is AU$362
includes taxes & fees
9 Nov - 10 Nov
Romantic studio • Bikes included • Near the 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 Holiday Homes information

Number of reviews
971
Accommodation
0 Holiday Homes
Lowest Price
AU$296
Highest Price
AU$668

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