Holiday Homes in Legacy Trail

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Our top choices for Legacy Trail holiday homes

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
Siesta Heron Suites & Villas

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

North Port
10.0 out of 10, Exceptional, (12)
"Very cute and cozy home in North Port FL close to shops and not a far drive to the beach. "
United States
James Y.
The price is NZ$338
includes taxes & fees
10 Dec - 11 Dec
Nestled in North Port. Updated 2 Bed / 1 Bath.

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (53)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is NZ$507
includes taxes & fees
18 Dec - 19 Dec
Siesta Key Island Rentals

Old Floridian cottage in Historic Gulf Village

Olde Englewood Village
9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is NZ$431
includes taxes & fees
10 Dec - 11 Dec
Old Floridian cottage in Historic Gulf Village

8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

South Venice
10.0 out of 10, Exceptional, (42)
"We had a wonderful time! The house was perfect and such a great location."
United States
Kellee N.
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

Oakland Hills
9.8 out of 10, Exceptional, (15)
"It was beautiful especially Boca Grande, went on a charter fish trip which was amazing. The property was also amazing nice dock and canoed the first day it was fun but then we saw a lot of gators but overall would come again! "
United States
Caleb R.
The price is NZ$568
includes taxes & fees
15 Dec - 16 Dec
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

Beautiful home with very private heated pool minutes from the beach

South Venice
10.0 out of 10, Exceptional, (31)
"Great vacation home. Loved the pool area and great location. The home had everything you need for cooking or going to the beach. Manasota beach was great to spend the day. Thanks again for your beautiful vacation home!"
United States
mickey m.
The price is NZ$633
includes taxes & fees
10 Dec - 11 Dec
Beautiful home with very private heated pool minutes from the beach

Stylish house minutes from the beach

South Venice
9.6 out of 10, Exceptional, (26)
"Great location and safe neighborhood. Definitely will stay again if available."
United States
Luis M.
The price is NZ$598
includes taxes & fees
10 Dec - 11 Dec
Stylish house minutes from the beach

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

2.0 star property
Sabal Harbour
10.0 out of 10, Exceptional, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is NZ$541
includes taxes & fees
17 Dec - 18 Dec
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Waterfront Getaway, a Boating Paradise

Englewood
10.0 out of 10, Exceptional, (46)
"Great place to stay with your boat."
United States
arthur n.
The price is NZ$518
includes taxes & fees
21 Dec - 22 Dec
Waterfront Getaway, a Boating Paradise

Coastal duplex with private beach access & deck - dog-friendly

Manasota Key
8.4 out of 10, Very good, (12)
"Great place to stay. "
United States
Scott
The price is NZ$660
includes taxes & fees
10 Dec - 11 Dec
Coastal duplex with private beach access & deck - dog-friendly

The Hideaways at Point Pleasant (Palm Side)

Bradenton
10.0 out of 10, Exceptional, (168)
"perfect location and size for what we were looking for"
United States
michael w.
The price is NZ$443
includes taxes & fees
13 Dec - 14 Dec
The Hideaways at Point Pleasant (Palm Side)

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

Bradenton
9.4 out of 10, Exceptional, (67)
"Great place to stay!"
United States
Wendi B.
The price is NZ$240
includes taxes & fees
10 Dec - 11 Dec
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

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

Southgate
10.0 out of 10, Exceptional, (69)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
The price is NZ$535
includes taxes & fees
9 Jan - 10 Jan 2026
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Charming home near Anna Maria Island with Jacuzzi

2.0 star property
Bradenton
10.0 out of 10, Exceptional, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
United States
Kyle S.
The price is NZ$512
includes taxes & fees
13 Dec - 14 Dec
Charming home near Anna Maria Island with Jacuzzi

Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!

port charlotte
9.6 out of 10, Exceptional, (60)
"Peaceful - beautiful back yard area"
United States
Carmen R.
The price is NZ$577
includes taxes & fees
16 Dec - 17 Dec
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Sarasota
9.6 out of 10, Exceptional, (35)
"Great place, clean, fully stocked kitchen, very convenient location. Would definitely stay again."
United States
Nan G.
The price is NZ$768
includes taxes & fees
10 Dec - 11 Dec
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Beautiful Blue Beach House Kids & Pets OK

Bradenton
10.0 out of 10, Exceptional, (33)
"We were visiting Florida to celebrate my nephews birthday at the beach! We enjoyed the house and the beach! The family had a great time!"
United States
Eileen G.
The price is NZ$1,016
includes taxes & fees
10 Dec - 11 Dec
Beautiful Blue Beach House Kids & Pets OK

Myakka River

Venice
9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is NZ$795
includes taxes & fees
22 Dec - 23 Dec
Myakka River

Newly renovated cozy beach house.

South Venice
10.0 out of 10, Exceptional, (6)
"The location was very convenient to the beach. It was a beautiful location."
United States
Carla C.
The price is NZ$559
includes taxes & fees
10 Dec - 11 Dec
Newly renovated cozy beach house.
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
775
Accommodation
1182 Holiday Homes
Lowest Price
NZ$240
Highest Price
NZ$1,016

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