A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Legacy Trail vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,923 reviews)
"Amazing resort,"
United States
kurt
The price is P8,444
P11,165 total
includes taxes & fees
Sep 29 - Sep 30
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,453 reviews)
"This place was perfect!"
United States
Kat
The price is P7,651
P8,646 total
includes taxes & fees
Sep 29 - Sep 30
Hibiscus Suites - Gateway to Siesta Key
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

3. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (185 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is P14,001
P15,821 total
includes taxes & fees
Sep 29 - Sep 30
SeaSpray Resort
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,310 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is P10,301
P12,699 total
includes taxes & fees
Sep 29 - Sep 30
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (684 reviews)
"Great stay!!"
United States
Genghis
The price is P11,808
P13,343 total
includes taxes & fees
Sep 29 - Sep 30
A Beach Retreat
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is P6,447
P20,357 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Island Rentals
A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

7. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (834 reviews)
"I loved this hotel"
United States
Raisare
The price is P18,055
P22,167 total
includes taxes & fees
Oct 7 - Oct 8
Bridgewalk Resort
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

8. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (471 reviews)
"Great place to stay,"
United States
Wilson
The price is P10,724
P13,572 total
includes taxes & fees
Sep 30 - Oct 1
Pelican Post at Anna Maria Island Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Search for holiday rentals in Legacy Trail on Expedia! You can easily find your home rentals, villas, holiday apartments in Legacy Trail using one of the methods below:

  • View our selection of featured holiday rentals in Legacy Trail
  • Use the map to find apartments and other holiday homes in the Legacy Trail neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Legacy Trail while they last

Look no further and take a look at our great range of rental properties in Legacy Trail!