Legacy Trail Vacation Rentals

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Our top choices for Legacy Trail holiday rentals

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5154)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is RM518
RM678 total
includes taxes & fees
17 Dec - 18 Dec
Tropical Beach Resorts
3.5 star property
9.6 out of 10, Exceptional, (300)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
The price is RM1,633
RM2,054 total
includes taxes & fees
17 Dec - 18 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1174)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
2.5 star property
8.6 out of 10, Excellent, (2213)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (246)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
Kon Tiki Inn

Apartment in Bradenton Beach

Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (332)
"Fabulous stay! Super clean!"
United States
Sarah
The price is RM776
RM982 total
includes taxes & fees
17 Dec - 18 Dec
Pelican Post at 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, (400)
"Beautiful location. Walking distance to beach. "
United States
Maria
The price is RM695
RM879 total
includes taxes & fees
21 Dec - 22 Dec
Haley's at The Anna Maria Island Inn

Apartment in Bradenton Beach

Seabreeze at Anna Maria Island Inn
3.0 star property
8.8 out of 10, Excellent, (57)
"Everything was great!!!!"
United States
David
The price is RM1,973
RM2,230 total
includes taxes & fees
26 Dec - 27 Dec
Seabreeze at Anna Maria Island Inn

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (576)
A Beach Retreat

Apartment in Siesta Key

The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (345)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House

Apartment in Casey Key

Casey Key Resort - Gulf Shores
3.0 star property
8.4 out of 10, Very good, (264)
"Amazing place"
United States
Ricardo
Casey Key Resort - Gulf Shores

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 RM438
RM992 total
includes taxes & fees
17 Dec - 18 Dec
Tiny House Siesta

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 RM761
RM1,684 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas

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 RM776
RM1,103 total
includes taxes & fees
17 Dec - 18 Dec
The Inn On Siesta Key

Aparthotel in Bridge Street

Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (766)
"Great stay!"
United States
Sufyan
The price is RM1,046
RM1,182 total
includes taxes & fees
30 Dec - 31 Dec
Bridgewalk Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (78)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is RM1,265
RM1,429 total
includes taxes & fees
21 Dec - 22 Dec
SeaSpray Resort
3.0 star property
The price is RM299
RM918 total
includes taxes & fees
17 Dec - 18 Dec
Relax in Hot Tub, Walk to Springs: North Port Home

Condo in Holmes Beach

Alamanda Villas
3.5 star property
10.0 out of 10, Exceptional, (3)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
The price is RM937
RM1,882 total
includes taxes & fees
18 Dec - 19 Dec
Alamanda 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

Holiday Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (54)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is RM570
RM1,256 total
includes taxes & fees
18 Dec - 19 Dec
Siesta Key Island Rentals
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

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