Legacy Trail Holiday Houses

Legacy Trail Holiday Homes
Florida
United States of America
Holiday Homes
Expedia.co.nz

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A wooden pathway surrounded by dense greenery and trees.

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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 stainless steel appliances, a central island with bar stools, and a window with blinds.

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.

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 NZ$552

NZ$552

includes taxes & fees

29 Oct - 30 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 living room with a flat-screen TV, teal armchairs, a striped rug, and a white cabinet with yellow items.

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 NZ$646

NZ$646

includes taxes & fees

31 Oct - 1 Nov

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 bedroom with a bed, a nightstand, a mirror, a window with curtains, and wall art.

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 NZ$389

NZ$389

includes taxes & fees

22 Nov - 23 Nov

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

A vase with dried plants on a wooden table, a decorative metal piece on the wall, and a small green bottle beside the vase.

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

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

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

4. 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 NZ$554

NZ$554

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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 NZ$708

NZ$708

includes taxes & fees

29 Oct - 30 Oct

[lounge like locals] walk to siesta beach +bikes

A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

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

6. 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 NZ$733

NZ$733

includes taxes & fees

31 Oct - 1 Nov

Island Villa | Cozy Beach Retreat | Walk to Village

A compact, well-lit interior with a bunk bed, seating area, kitchenette, and a television.

A beach path leading to a sandy beach with a signboard advertising the beach.

A wooden deck with a welcome sign, outdoor seating, and a covered area with chairs and tables.

A compact, modern interior with a loft bedroom, a seating area with a laptop, and a kitchenette.

7. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta

Sarasota

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."

Kadina A.

The price is NZ$309

NZ$309

includes taxes & fees

6 Nov - 7 Nov

The Mermaid at Tiny House Siesta

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

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.

A pathway leading to a building with a wooden fence and vegetation on the left.

8. 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)

"Beautiful home, perfect location! Would come back again. Thank you!!! "

Joe V.

The price is NZ$497

NZ$497

includes taxes & fees

26 Oct - 27 Oct

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

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

A modern living room with a sectional sofa, a dining table with chairs, and a ceiling fan.

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

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

9. 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 NZ$375

NZ$375

includes taxes & fees

26 Oct - 27 Oct

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

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

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

A kitchen with white cabinets, a white stove, a microwave, and a dishwasher. There is a teal-colored countertop and a rug on the floor.

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.

10. 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 NZ$553

NZ$553

includes taxes & fees

29 Oct - 30 Oct

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

A kitchen with a stainless steel sink, dark cabinets, a countertop, and a TV in the background.

A beach at sunset with people in the water and a bird flying.

A living room with a beige sectional sofa, a glass coffee table, and a TV. There's a kitchen area with a fridge, microwave, and sink.

A bedroom with a bed, a pillow with text, a nightstand, a lamp, and a painting of a beach scene.

11. Tropical and Tranquil Bradenton hideaway

Tropical and Tranquil Bradenton hideaway

River Pointe

9.2 out of 10, Wonderful, (22 reviews)

9.2/10

Wonderful

(22 reviews)

"Very clean - perfect location for what we needed. Well appointed and amenities were exactly as listed. Check in and out was easy and communication with host was prompt and friendly. Enjoyed our stay and the home. Would highly recommend and hope to stay again sometime!"

Jill B.

The price is NZ$566

NZ$566

includes taxes & fees

27 Oct - 28 Oct

Tropical and Tranquil Bradenton hideaway

A covered patio with a ceiling fan, white chairs, and a glass table.

A modern kitchen with white cabinetry, a built-in microwave, and a large oven.

A dining area with a glass table, chairs, and a buffet bowl. There is a sofa and a ceiling fan in the background.

A residential area with houses, palm trees, and a view of the ocean.

12. Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Village

9.6 out of 10, Exceptional, (22 reviews)

9.6/10

Exceptional

(22 reviews)

"Beautiful little place. Super clean. Has everything you need. Great communication and quick response to any need. Fast walk to the beach and village."

Ivette R.

The price is NZ$1,064

NZ$1,064

includes taxes & fees

26 Oct - 27 Oct

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

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

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

A dining area with a table, chairs, a refrigerator, and a window with curtains.

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 NZ$522

NZ$522

includes taxes & fees

28 Oct - 29 Oct

The Hideaways at Point Pleasant (Palm Side)

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

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 covered patio area with wicker furniture, a ceiling fan, and a view into the house through glass doors.

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 NZ$401

NZ$401

includes taxes & fees

27 Oct - 28 Oct

Lakeview Bradenton Rental Near Beaches & IMG

A spacious living area with a large TV, ceiling fans, and a dining area with a table and chairs.

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

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

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

15. 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 NZ$652

NZ$652

includes taxes & fees

29 Oct - 30 Oct

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

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

A kitchen with white cabinets, a microwave, a stove, and a countertop. There are shelves on the wall above the countertop.

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

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

16. 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 Hideaways at Point Pleasant (Pine Side)

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

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

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

A single-story house with a garage, a red door, and a well-maintained lawn.

17. 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 NZ$603

NZ$603

includes taxes & fees

26 Oct - 27 Oct

Pet-Friendly Stay 4miles to Beach

A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

A bedroom with a bed, nightstand, lamp, and a ceiling fan.

A kitchen with white cabinets, a stainless steel sink, a microwave, an oven, and a trash can.

A living room with a sofa, a TV, a small table, and a chair. There is a door leading to another room.

18. The Dolphin

The Dolphin

Nokomis

9.8 out of 10, Exceptional, (21 reviews)

9.8/10

Exceptional

(21 reviews)

"The cottage was comfortable and the pool was relaxing. "

daniel

The price is NZ$583

NZ$583

includes taxes & fees

26 Oct - 27 Oct

The Dolphin

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 modern living room with a wooden panel wall, a flat-screen TV, a dining table with bar stools, and a sofa.

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.

19. 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)

"The host was so nice I’ll be staying there again!"

Melissa

The price is NZ$412

NZ$412

includes taxes & fees

26 Oct - 27 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 single-story house with a front door, a small porch, and a wooden fence in the background.

A modern kitchen with white cabinets, a dining area with a round table and white chairs, and a wooden floor.

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

20. 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 NZ$750

NZ$750

includes taxes & fees

26 Oct - 27 Oct

Backyard Oasis & Resort Style Pool

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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Legacy Trail Holiday Homes information

Number of reviews	607
Accommodation	0 Holiday Homes
Lowest Price	NZ$309
Highest Price	NZ$1,064

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Book Holiday Homes in Legacy Trail on Expedia.com

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

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

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

7. The Mermaid at Tiny House Siesta

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

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

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

11. Tropical and Tranquil Bradenton hideaway

12. Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

13. The Hideaways at Point Pleasant (Palm Side)

14. Lakeview Bradenton Rental Near Beaches & IMG

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

16. The Hideaways at Point Pleasant (Pine Side)

17. Pet-Friendly Stay 4miles to Beach

18. The Dolphin

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

20. Backyard Oasis & Resort Style Pool

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