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Our top choices for Legacy Trail holiday homes

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

A modern kitchen with white cabinets, a black countertop, and a red coffee maker.

A wooden deck overlooking a calm river, surrounded by lush greenery and trees.

A spacious living area with a large bed, a sofa, a small table, and a kitchen in the background.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property

Siesta Key

8.4 out of 10, Very good, (46 reviews)

8.4/10

Very good

(46 reviews)

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

Christopher Robert

The price is €292

€292

includes taxes & fees

18 Oct - 19 Oct

Siesta Heron Suites & Villas

A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

A pool area with lounge chairs and a sign that reads "Life is better in flip flops."

A modern kitchen with white cabinets, a blue countertop, and a dining area with a round table and grey chairs.

A modern kitchen with a dining area, featuring a white countertop, blue cabinets, and a round table with chairs.

2. Dolphin Villa | Pool | Steps to Siesta Key Village

Dolphin Villa | Pool | Steps to Siesta Key Village

Siesta Key Village

9.4 out of 10, Exceptional, (17 reviews)

9.4/10

Exceptional

(17 reviews)

"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "

Amy

The price is €333

€333

includes taxes & fees

22 Oct - 23 Oct

Dolphin Villa | Pool | Steps to Siesta Key Village

A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

A modern kitchen with a dining area, a flat-screen TV, and a bookshelf with various items.

A room with a wooden desk, a chair, a television, and shelves with books and decorative items.

A covered patio with a table and chairs, large windows, and a ceiling fan.

3. 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)

10/10

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."

Emma

The price is €227

€227

includes taxes & fees

19 Oct - 20 Oct

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

A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

A kitchen with white cabinets, a granite countertop, a microwave, an oven, and a refrigerator.

A dining area with a round table set for four, surrounded by chairs. There is a kitchen area with white cabinets and a microwave.

A living room with a white sofa, striped armchairs, a wooden coffee table, a ceiling fan, and a TV on the wall.

4. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key

Sarasota

9.8 out of 10, Exceptional, (85 reviews)

9.8/10

Exceptional

(85 reviews)

"Clean and convenient"

Scott H.

2 miles to #1 Beach Siesta Key

A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

A bathroom with a marble countertop, a copper vessel sink, dark cabinets, and a large mirror.

A modern living room with a sectional sofa, a dining area with yellow curtains, a kitchen with white cabinets, and a ceiling fan.

A bedroom with a bed, bedside tables, a ceiling fan, and curtains.

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)

9.8/10

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."

Moreixa C.

The price is €295

€295

includes taxes & fees

18 Oct - 19 Oct

[lounge like locals] walk to siesta beach +bikes

A modern living room with a large window, a flat-screen TV, and a potted plant.

A kitchen with a stove, coffee maker, and spice jars on the countertop.

A modern, white-themed room with a dining table, chairs, a ceiling fan, and built-in shelving with plants.

A modern building with a white exterior, a large sliding glass door, and a number "7904" on the wall.

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)

10/10

Exceptional

(25 reviews)

"Every part of this stay was perfect! "

Stephen P.

The price is €199

€199

includes taxes & fees

18 Oct - 19 Oct

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

A spacious living room with a high ceiling, a ceiling fan, a dining area with orange chairs, and a large gray sofa.

A modern kitchen with white cabinets, a coffee maker, and a sink. There is a window with blinds and a door leading to a balcony.

A modern kitchen with white cabinets, a central island, and a dining area with orange chairs and a red table.

A modern living room with a grey sectional sofa, a round ottoman, a small table with a lamp, and a wall-mounted TV.

7. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village

Siesta Key Village

8.4 out of 10, Very good, (14 reviews)

8.4/10

Very good

(14 reviews)

"Great place to stay and very close to restaurants "

Amber B.

The price is €355

€355

includes taxes & fees

20 Oct - 21 Oct

Island Villa | Cozy Beach Retreat | Walk to Village

A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

A neatly made bed with white linens and a wooden bench in front. There are two bedside tables with lamps, a painting above the bed, and a patterned rug on the floor.

A small kitchen with a wooden countertop, three stools, and a potted plant.

A covered patio area with string lights, a door with a wreath, and a bench.

8. 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)

10/10

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!"

Sierra B.

The price is €329

€329

includes taxes & fees

8 Nov - 9 Nov

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

A house with a porch, number 203, and a ceiling fan.

A two-story house with a covered porch and a small front yard.

A compact kitchen with a white refrigerator, a dining table with red chairs, and a window with curtains.

A living room with a red sofa, a small table, and a TV. There is a kitchen area with a refrigerator and a sink.

9. The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)

Bradenton

9.8 out of 10, Exceptional, (182 reviews)

9.8/10

Exceptional

(182 reviews)

"Great location and wonderful place to stay."

Theresa H.

The price is €274

€274

includes taxes & fees

17 Oct - 18 Oct

The Hideaways at Point Pleasant (Pine Side)

A clear swimming pool with a pink float, surrounded by a covered area with chairs and a wooden fence.

A kitchen with a dining area, wooden cabinets, a black refrigerator, and a window with blinds.

A bedroom with a bed, a ceiling fan, a window with curtains, a floor lamp, and a painting on the wall.

A house with a red door, a patio with chairs, and a garden with tropical plants.

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, (128 reviews)

9.4/10

Exceptional

(128 reviews)

"Barb was very helpful and made numerous quality suggestions for nearby restaurants and activities."

Mitzy B.

The price is €257

€257

includes taxes & fees

18 Oct - 19 Oct

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

A lifeguard tower with a blue umbrella on a sandy beach.

A wooden bench, a metal showerhead, and an anchor decoration on a wall.

A sunlit indoor ping pong table with a net, surrounded by large windows and a patterned wall.

A lakeside patio with three blue Adirondack chairs and a small table, surrounded by a white fence and a green umbrella.

11. Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Bradenton

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Great spot, lovely back yard and pool, so relaxing we loved it."

Cadence

The price is €346

€346

includes taxes & fees

29 Oct - 30 Oct

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

A balcony with two blue chairs and a small table, overlooking a lake with trees and a sunset.

A modern bedroom with a four-poster bed, a ceiling fan, a nightstand with a lamp, and a large window with a view of greenery.

A spacious living room with a sofa, chairs, a coffee table, and a television. There is a large window with a view of a garden and a door leading outside.

A large outdoor swimming pool with a circular center, surrounded by palm trees and lounge chairs.

12. 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)

10/10

Exceptional

(35 reviews)

"Great location! I loved the sunsets on the back patio!"

Megan R.

The price is €298

€298

includes taxes & fees

25 Oct - 26 Oct

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

A two-story house with a covered porch, a small front yard, and a clear blue sky.

A covered patio with a ceiling fan, two chairs, a table, and a door with a window.

A compact living space with a kitchen, dining area, and a living room featuring a television, sofa, and decorative wall art.

A living room with a blue sofa, a coffee table, a lamp, a door, and a small cabinet.

13. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)

Bradenton

10.0 out of 10, Exceptional, (177 reviews)

10/10

Exceptional

(177 reviews)

"Great downtown location! We enjoyed our stay!"

Diane M.

The price is €274

€274

includes taxes & fees

19 Oct - 20 Oct

The Hideaways at Point Pleasant (Palm Side)

A modern bathroom with a glass shower enclosure, a toilet, and a sink.

A modern kitchen with stainless steel appliances, white cabinets, and a central island.

A kitchen counter with various items including a box of Mikado toilet paper, a Snuggle tissue box, a coffee mug, and a kitchen sign.

A dining area with a dark wooden table, four chairs, and a hanging lamp.

14. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG

South Bradenton

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Very clean and comfortable. "

Dee F.

The price is €219

€219

includes taxes & fees

20 Oct - 21 Oct

Lakeview Bradenton Rental Near Beaches & IMG

A modern living room with a blue sofa, yellow armchair, and a white coffee table.

A bedroom with a bed, a green armchair, a yellow dresser, and a TV displaying a tropical scene.

A modern kitchen with white cabinets, a blue countertop, and a stainless steel stove.

15. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Siesta Key Village

9.0 out of 10, Wonderful, (15 reviews)

9.0/10

Wonderful

(15 reviews)

"We loved staying here for my bachelorette!"

Kelsey E.

The price is €375

€375

includes taxes & fees

18 Oct - 19 Oct

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

A swimming pool with a view of a lake, surrounded by a covered patio area with chairs and a slide.

A paved pathway leading to a hammock and a bench by a lake.

A spacious living room with a dark green sofa, a beige sofa, and a coffee table. There is a dining area with a table and chairs, and a kitchen with wooden cabinets and a refrigerator.

16. IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!

IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!

South Bradenton

9.8 out of 10, Exceptional, (140 reviews)

9.8/10

Exceptional

(140 reviews)

"Beautiful pool, nice kitchen, and close to Anna Marie Island."

Gary B.

The price is €486

€486

includes taxes & fees

18 Oct - 19 Oct

IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!

A beach with a clear sky, calm sea, and footprints on the sand.

A modern living room with a sofa, a TV mounted on a wooden panel, and a kitchen area with a refrigerator, sink, and countertop.

A neatly made bed with white linens, two bedside tables with lamps, and a window with curtains.

A single-story house with a green door, a small front porch, and a number '131' on the side.

17. 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)

10/10

Exceptional

(6 reviews)

"Cute, clean, comfortable beds. Perfect for our needs."

Sharon K.

The price is €220

€220

includes taxes & fees

18 Oct - 19 Oct

Charming 2-bedroom house in Englewood with WiFi and AC

A swimming pool with a surrounding garden and a covered area with a metal roof.

A covered outdoor seating area with two lounge chairs, potted plants, and a tiled floor.

A neatly arranged bedroom with a bed, bedside lamps, a hanging light fixture, a patterned rug, and a view through a window.

A single-story house with a front door, a small porch, and a wooden fence in the background.

18. Backyard Oasis & Resort Style Pool

Backyard Oasis & Resort Style Pool

Bradenton

10.0 out of 10, Exceptional, (70 reviews)

10/10

Exceptional

(70 reviews)

"Great house! Super clean and amazing pool area. Would stay again!"

Katina M.

The price is €379

€379

includes taxes & fees

18 Oct - 19 Oct

Backyard Oasis & Resort Style Pool

A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

A covered outdoor area with a pool, a table with chairs, and a ceiling fan.

A dining area with a blue tablecloth, wooden chairs, and a plant centerpiece.

A kitchen with wooden cabinets, a stainless steel refrigerator, a dishwasher, and a window with a view of greenery.

19. Siesta beach....one and only

Siesta beach....one and only

Sarasota

9.4 out of 10, Exceptional, (221 reviews)

9.4/10

Exceptional

(221 reviews)

"Nice stay perfect location"

tom f.

The price is €432

€432

includes taxes & fees

21 Oct - 22 Oct

Siesta beach....one and only

A dining table set with brown bowls and glasses, surrounded by chairs, with a view of palm trees through a glass door.

A backyard with a round glass table, two wooden chairs, a fire pit, and a white fence.

A kitchen with a double sink, fruit baskets, and a window with a view of trees.

A room with two green chairs, a small wooden table with a vase, and a floor lamp.

20. Pet-Friendly Stay 4miles to Beach

Pet-Friendly Stay 4miles to Beach

Venice Gardens

10.0 out of 10, Exceptional, (7 reviews)

10/10

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."

Jessica

The price is €309

€309

includes taxes & fees

18 Oct - 19 Oct

Pet-Friendly Stay 4miles to 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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Holiday Homes in Legacy Trail

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Legacy Trail holiday homes

1. Siesta Heron Suites & Villas

2. Dolphin Villa | Pool | Steps to Siesta Key Village

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

4. 2 miles to #1 Beach Siesta Key

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

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

7. Island Villa | Cozy Beach Retreat | Walk to Village

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

9. The Hideaways at Point Pleasant (Pine Side)

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

11. Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

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

13. The Hideaways at Point Pleasant (Palm Side)

14. Lakeview Bradenton Rental Near Beaches & IMG

15. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

16. IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!

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

18. Backyard Oasis & Resort Style Pool

19. Siesta beach....one and only

20. Pet-Friendly Stay 4miles to Beach

Find holiday rentals that suit your style

Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Legacy Trail Holiday Homes information

Explore a world of travel with Expedia