Legacy Trail Vacation Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Legacy Trail holiday rentals

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

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
Front of property – evening/night
Captiva Beach Resort

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
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, (2213)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Living area
SeaSpray 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 RM1,266
RM1,431 total
includes taxes & fees
17 Dec - 18 Dec
SeaSpray Resort
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, (300)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
The price is RM1,667
RM2,091 total
includes taxes & fees
15 Jan - 16 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
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, (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
Front of property
The Ringling Beach House

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
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, (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
Outdoor pool, pool umbrellas, pool loungers
Bridgewalk Resort

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 RM1,047
RM1,183 total
includes taxes & fees
17 Dec - 18 Dec
Bridgewalk Resort
Exterior
Seabreeze at 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
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 RM438
RM993 total
includes taxes & fees
17 Dec - 18 Dec
Tiny House Siesta
Outdoor pool
Alamanda Villas

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 RM938
RM1,884 total
includes taxes & fees
17 Dec - 18 Dec
Alamanda Villas
Exterior
Kon Tiki Inn

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
Exterior
Siesta Key Island Rentals

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
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, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat
Living area
Swivel On Anchor

Houseboat in Bradenton

Swivel On Anchor
2.5 star property
2.0 out of 10, (2)
"Was supposed to depart at 6. I showed up at 5:15 and waited until 6 before i started calling their phone number. Had to call 15 times before i got an answer and they said they didnt know i booked it. Said they would have a captain out in 40 minutes. Called me back 20 minutes later to tell me they didnt have a captain. This was 2 weeks ago and i still haven't received a refund. There's either super unprofessional or scam artists."
United States
Chris
The price is RM362
RM716 total
includes taxes & fees
26 Dec - 27 Dec
Swivel On Anchor
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 RM776
RM1,103 total
includes taxes & fees
17 Dec - 18 Dec
The Inn On Siesta Key
Garden
Siesta Palms By the Beach

Aparthotel in South Village

Siesta Palms By the Beach
3.5 star property
9.4 out of 10, Exceptional, (137)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach

Holiday Home in Venice Island

Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (241)
"Clean, but very outdated. "
United States
Tim
Tropical Villas of Venice Beach
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
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

Carlisle Inn

Carlisle Inn

10/10 Excellent
"We booked this hotel to stay at during my sons soccer tournaments. Hotel was very clean, staff was super courteous, great stay. The free breakfast was amazing. And, you can’t go wrong with a fresh, complimentary cookies in the lobby. Will absolutely stay again if in town."
Maria 1-night trip
Posted 16 hours ago
Carlisle Inn

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