Legacy Trail Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Legacy Trail holiday rentals

Property grounds
Tropical Beach Resorts

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5184)
"Great location, value, clean, friendly staff. Will definitely stay there again. "
United States
JoAnna
The price is HK$1,116
HK$1,437 total
includes taxes & fees
5 Jan - 6 Jan 2026
Tropical Beach Resorts
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (303)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is HK$3,103
HK$3,902 total
includes taxes & fees
29 Jan - 30 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

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2221)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key
Exterior
Kon Tiki Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (248)
"Was close to the beach! Enjoyed having the little kitchen. Very quiet. Would definitely stay again."
United States
Linda
The price is HK$2,046
HK$2,312 total
includes taxes & fees
20 Jan - 21 Jan 2026
Kon Tiki Inn
Outdoor pool, pool umbrellas, pool loungers
Bridgewalk Resort

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (768)
"Great stay!"
United States
Sufyan
The price is HK$1,810
HK$2,046 total
includes taxes & fees
18 Jan - 19 Jan 2026
Bridgewalk Resort
Beach nearby, white sand, sun-loungers, beach towels
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (405)
"Beautiful location. Walking distance to beach. "
United States
Maria
The price is HK$1,825
HK$2,310 total
includes taxes & fees
2 Jan - 3 Jan 2026
Haley's at The Anna Maria Island Inn
Exterior
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (335)
"Easy access to Bridge St... Walk quick to beach. Quiet pool nice ... They can definitely improve the Internet as that was spotty. "
United States
Marc
The price is HK$1,825
HK$2,310 total
includes taxes & fees
2 Jan - 3 Jan 2026
Pelican Post at Anna Maria Island Inn
On the beach, white sand
A Beach Retreat

A Beach Retreat

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

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is HK$777
HK$1,822 total
includes taxes & fees
11 Jan - 12 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

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is HK$3,432
HK$4,309 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Inn On Siesta Key
Private kitchen
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

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
The price is HK$1,402
HK$3,148 total
includes taxes & fees
12 Jan - 13 Jan 2026
Siesta Heron Suites & Villas
Exterior
Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (65)
"Very great stay will stay again "
United States
Joseph
The price is HK$1,459
HK$1,847 total
includes taxes & fees
7 Jan - 8 Jan 2026
Seabreeze at Anna Maria Island Inn
Living area
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (82)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is HK$2,081
HK$2,352 total
includes taxes & fees
12 Jan - 13 Jan 2026
SeaSpray Resort
Fridge, microwave, stovetop, coffee/tea maker
Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is HK$583
HK$1,341 total
includes taxes & fees
3 Jan - 4 Jan 2026
Charming cottage for 2 across warm mineral springs park
Beach nearby, white sand, beach umbrellas, beach towels
Palm Tree Villas

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
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

Charming home near Anna Maria Island with Jacuzzi

Charming home near Anna Maria Island with Jacuzzi
2.0 star property
Bradenton
10.0 out of 10, Exceptional, (15)
"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$1,127
HK$2,416 total
includes taxes & fees
14 Jan - 15 Jan 2026
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

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bayshore Gardens
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$1,341 total
includes taxes & fees
1 Jan - 2 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

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

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.4 out of 10, Exceptional, (67)
"Great place to stay!"
United States
Wendi B.
The price is HK$816
HK$1,209 total
includes taxes & fees
5 Jan - 6 Jan 2026
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Property grounds
Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village

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 HK$1,154
HK$2,361 total
includes taxes & fees
12 Jan - 13 Jan 2026
Old Floridian cottage in Historic Gulf Village
Dining
Nestled in North Port. Updated 2 Bed / 1 Bath.

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, (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.
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Room was spacious and very clean. The hotel was beautifully decorated. The staff friendly and courteous. I rate this hotel a 10 exceeded my expectations. Breakfast was amazing!! Would definitely recommend to my friends and family !!"
Yadira 1-night trip
Posted 3 days ago
Kompose Boutique Hotel

Find out more about Legacy Trail

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