Legacy Trail, FL Vacation Homes from ￥37,252

Legacy Trail Vacation Homes
Florida
United States of America
Expedia.co.jp

Legacy Trail Travel Guide Hotels in Legacy Trail Vacation Rentals in Legacy Trail Flights to Legacy Trail Car Rentals in Legacy Trail Legacy Trail Vacation Packages

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Our top choices for Legacy Trail vacation homes

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

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

1. 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 ￥16,784

￥16,784

￥39,542 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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

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

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 ￥18,244

￥18,244

￥59,506 total

includes taxes & fees

Oct 22 - Oct 23

Dolphin Villa | Pool | Steps to Siesta Key Village

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 single-story house with a garage, a small front yard, and a tree.

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.

3. 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.

The price is ￥18,561

￥18,561

￥53,733 total

includes taxes & fees

Oct 18 - Oct 19

2 miles to #1 Beach Siesta Key

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

4. 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 ￥16,419

￥16,419

￥62,504 total

includes taxes & fees

Oct 20 - Oct 21

Island Villa | Cozy Beach Retreat | Walk to Village

A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

A turquoise two-story house with a white garage door, surrounded by a wooden fence and palm trees.

A living room with a grey sofa, teal ottoman, and a potted plant.

A living room with a sofa, a teal ottoman, a framed picture of a wave, a bamboo plant, and a lamp.

5. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway

Siesta Key

9.8 out of 10, Exceptional, (34 reviews)

9.8/10

Exceptional

(34 reviews)

"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"

Tim T.

The price is ￥18,100

￥18,100

￥53,473 total

includes taxes & fees

Oct 19 - Oct 20

[escape to paradise] siesta key beach getaway

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

A white door with a green wreath, a wall-mounted light fixture, and a framed inspirational quote.

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.

6. 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 price is ￥25,224

￥25,224

￥56,305 total

includes taxes & fees

Nov 8 - Nov 9

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

7. 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)

"This is a really nice place. Set back out of the way, but perfect walking distance to where the action is and to the RiverWalk! Very clean and so convenient! We will definetly back to this place!"

Bob W.

The price is ￥17,256

￥17,256

￥47,262 total

includes taxes & fees

Oct 19 - Oct 20

The Hideaways at Point Pleasant (Pine Side)

A modern kitchen with a large island, stainless steel appliances, and blue bar stools.

A modern kitchen with stainless steel appliances, a central island, and a dining area with a view of the living room.

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

An aerial view of a large, well-maintained sports field with multiple soccer goals, surrounded by green areas and a small lake.

8. Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

Sarasota

9.8 out of 10, Exceptional, (8 reviews)

9.8/10

Exceptional

(8 reviews)

"This was a great stay for us. It was extremely clean and just as described."

Kenzie Q.

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

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

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

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

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

9. 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 ￥12,969

￥12,969

￥58,908 total

includes taxes & fees

Oct 29 - Oct 30

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

A modern kitchen with a bar area, a dining table, and a sofa in a living room.

A neatly made bed with a wooden headboard, a bedside lamp, and a painting on the wall.

A kitchen with a wooden island, white bar stools, and recessed lighting.

A living room with a sofa, a small table, and a chair. There is a sliding glass door leading to an outdoor area.

10. Mimosa Memories

Mimosa Memories

South Venice

9.6 out of 10, Exceptional, (41 reviews)

9.6/10

Exceptional

(41 reviews)

"Clean"

Hector G.

The price is ￥14,278

￥14,278

￥48,259 total

includes taxes & fees

Oct 14 - Oct 15

Mimosa Memories

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

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.

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)

10/10

Exceptional

(35 reviews)

The price is ￥17,133

￥17,133

￥51,644 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A hallway with a bench, a door, and a wall-mounted bag rack.

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.

12. 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 ￥15,491

￥15,491

￥37,653 total

includes taxes & fees

Nov 3 - Nov 4

Lakeview Bradenton Rental Near Beaches & IMG

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

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

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

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 ￥17,256

￥17,256

￥47,262 total

includes taxes & fees

Oct 19 - Oct 20

The Hideaways at Point Pleasant (Palm Side)

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.

14. 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 ￥20,936

￥20,936

￥68,511 total

includes taxes & fees

Oct 19 - Oct 20

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

A modern kitchen with grey cabinets, a wooden countertop, stainless steel appliances, and a tiled backsplash.

A living room with a sofa, a coffee table, a TV, and a ceiling fan.

A bedroom with a bed, a nightstand, a ceiling fan, a window, and a plant.

15. Path to Paradise.

Path to Paradise.

Olde Englewood Village

9.6 out of 10, Exceptional, (7 reviews)

9.6/10

Exceptional

(7 reviews)

"Great little spot!"

Matthew

The price is ￥13,072

￥13,072

￥43,729 total

includes taxes & fees

Oct 19 - Oct 20

Path to Paradise.

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.

An aerial view of a residential area with a large house featuring a spacious backyard, a swimming pool, and a view of the ocean.

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

16. 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 ￥19,235

￥19,235

￥73,955 total

includes taxes & fees

Oct 14 - Oct 15

Siesta beach....one and only

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

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

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.

17. 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 ￥19,504

￥19,504

￥69,413 total

includes taxes & fees

Oct 19 - Oct 20

Backyard Oasis & Resort Style Pool

A beachside restaurant with outdoor seating, palm trees, and a thatched-roof structure.

A modern kitchen with wooden cabinets, a glass dining table, and a hanging light fixture.

A kitchen with wooden cabinets, granite countertops, a white stove, and a refrigerator.

A house with a white door, a small porch, and a palm tree.

18. Luxury Family Home Near Downtown & Siesta Key Beach

Luxury Family Home Near Downtown & Siesta Key Beach

Alta Vista

9.8 out of 10, Exceptional, (82 reviews)

9.8/10

Exceptional

(82 reviews)

"Excellent property at a great value. Very clean and centrally located. "

Joseph C.

The price is ￥17,990

￥17,990

￥56,671 total

includes taxes & fees

Oct 19 - Oct 20

Luxury Family Home Near Downtown & Siesta Key Beach

A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

A kitchen with a stainless steel refrigerator, wooden dining table, and white cabinets.

A kitchen with white cabinets, a stainless steel refrigerator, and a window with blinds.

A marina with several boats docked at wooden piers.

19. LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

Sunny Shores

9.6 out of 10, Exceptional, (44 reviews)

9.6/10

Exceptional

(44 reviews)

"Superb value, quiet area, responsive owner, very nicely appointed; will definitely book again for next visit to Anna Maria Island!"

Bryce W.

The price is ￥12,744

￥12,744

￥74,743 total

includes taxes & fees

Oct 24 - Oct 25

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

A wooden staircase leading to a deck area with a striped umbrella and a table with chairs.

A room with a large window, a wooden shelf with books and a fire extinguisher, and a TV displaying a beach scene.

A cozy living room with a light blue sofa, colorful cushions, a starfish-patterned rug, a wooden TV stand, and a large window with a view of the ocean.

A cozy room with a teal sofa, a patterned rug, a metal shelving unit with various items, and a small table with a lamp.

20. Cute Carriage house , NR beaches, walk to Main st.

Cute Carriage house , NR beaches, walk to Main st.

Bradenton

9.8 out of 10, Exceptional, (28 reviews)

9.8/10

Exceptional

(28 reviews)

"We enjoyed staying here for our anniversary vacation"

Toby L.

The price is ￥13,931

￥13,931

￥37,252 total

includes taxes & fees

Oct 19 - Oct 20

Cute Carriage house , NR beaches, walk to Main st.

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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