Legacy Trail Holiday Rentals

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Legacy Trail holiday rentals

Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5171)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is HK$1,117
HK$1,438 total
includes taxes & fees
4 Jan - 5 Jan 2026
Tropical Beach Resorts
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (301)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is HK$3,272
HK$4,092 total
includes taxes & fees
21 Jan - 22 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2219)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (247)
"Lovely decor, very clean"
United States
Frederick
The price is HK$1,819
HK$2,055 total
includes taxes & fees
20 Jan - 21 Jan 2026
Kon Tiki Inn
Outdoor pool, pool umbrellas, pool loungers
Bridgewalk Resort

Aparthotel in Bridge Street

Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (767)
"Great stay!"
United States
Sufyan
The price is HK$1,855
HK$2,097 total
includes taxes & fees
19 Jan - 20 Jan 2026
Bridgewalk Resort
Beach nearby, white sand, sun-loungers, beach towels
Haley's at The Anna Maria Island Inn

Apartment in Holmes Beach

Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (403)
"Beautiful location. Walking distance to beach. "
United States
Maria
The price is HK$2,488
HK$3,149 total
includes taxes & fees
27 Dec - 28 Dec
Haley's at The Anna Maria Island Inn
Exterior
Pelican Post at Anna Maria Island Inn

Apartment in Bradenton Beach

Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (335)
"Fabulous stay! Super clean!"
United States
Sarah
The price is HK$2,285
HK$2,891 total
includes taxes & fees
27 Dec - 28 Dec
Pelican Post at Anna Maria Island Inn
On the beach, white sand
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (580)
"Great location, recent updates"
United States
Michael
A Beach Retreat
Living area
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is HK$832
HK$1,885 total
includes taxes & fees
5 Jan - 6 Jan 2026
Tiny House Siesta
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is HK$2,822
HK$3,673 total
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key
Private kitchen
Siesta Heron Suites & Villas

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is HK$1,419
HK$3,167 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas
Exterior
Seabreeze at Anna Maria Island Inn

Apartment in Bradenton Beach

Seabreeze at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (61)
"Very great stay will stay again "
United States
Joseph
The price is HK$2,239
HK$2,834 total
includes taxes & fees
5 Jan - 6 Jan 2026
Seabreeze at Anna Maria Island Inn
Living area
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (82)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is HK$2,057
HK$2,324 total
includes taxes & fees
4 Jan - 5 Jan 2026
SeaSpray Resort
Fridge, microwave, stovetop, coffee/tea maker
Charming cottage for 2 across warm mineral springs park

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is HK$583
HK$1,342 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming cottage for 2 across warm mineral springs park
Beach nearby, white sand, beach umbrellas, beach towels
Palm Tree Villas

Apartment in Holmes Beach

Palm Tree Villas
3.0 star property
9.2 out of 10, Wonderful, (172)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveller
Palm Tree Villas
Smart TV, stereo
Charming home near Anna Maria Island with Jacuzzi

Holiday Home in Bradenton

Charming home near Anna Maria Island with Jacuzzi
2.0 star property
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 HK$1,036
HK$2,298 total
includes taxes & fees
28 Dec - 29 Dec
Charming home near Anna Maria Island with Jacuzzi
Fridge, microwave, coffee/tea maker, dining tables
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Apartment in Bayshore Gardens

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
9.2 out of 10, Wonderful, (36)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is HK$583
HK$1,342 total
includes taxes & fees
31 Dec - 1 Jan 2026
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Terrace/patio
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Holiday Home in Bradenton

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
9.4 out of 10, Exceptional, (67)
"Great place to stay!"
United States
Wendi B.
The price is HK$700
HK$1,078 total
includes taxes & fees
29 Dec - 30 Dec
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Property grounds
Old Floridian cottage in Historic Gulf Village

Holiday Home in Olde Englewood Village

Old Floridian cottage in Historic Gulf Village
9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is HK$1,050
HK$2,298 total
includes taxes & fees
27 Dec - 28 Dec
Old Floridian cottage in Historic Gulf Village
Dining
Nestled in North Port. Updated 2 Bed / 1 Bath.

Holiday Home in North Port

Nestled in North Port. Updated 2 Bed / 1 Bath.
10.0 out of 10, Exceptional, (12)
"My husband's stay here was perfect for some time spent with older aunts/uncles in the area. This gave them a place to unwind, relax and such in between the visits. He said it was a very nice place to stay"
United States
Debbie S.
The price is HK$756
HK$1,823 total
includes taxes & fees
27 Dec - 28 Dec
Nestled in North Port. Updated 2 Bed / 1 Bath.
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

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

10/10 Excellent
"We checked in very late at night and the lady "
Emmeleen 1-night trip
Posted 3 days ago
Hibiscus Suites - Gateway to Siesta Key

Find out more about Legacy Trail

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