Legacy Trail Vacation Rentals

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Our top choices for Legacy Trail vacation rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (277 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
$115 nightly
The price is $129
May 19 - May 20
Total with taxes and fees
Kon Tiki Inn

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,487 reviews)
"This was such a great place to stay. The pool was GREAT and the beach access was fantastic"
United States
Laurie A
$184 nightly
The price is $208
May 21 - May 22
Total with taxes and fees
Tropical Beach Resorts

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (479 reviews)
"Clean room, staff was excellent. Close to downtown area and beach, all within walking distance. "
Canada
John
$133 nightly
The price is $150
May 29 - May 30
Total with taxes and fees
Venice Beach Villas

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,314 reviews)
"Excellent location, great place to stay! "
United States
Lynn
$145 nightly
The price is $163
May 18 - May 19
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (633 reviews)
"Love this place"
United States
Marialis
$221 nightly
The price is $249
May 18 - May 19
Total with taxes and fees
A Beach Retreat

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (800 reviews)
"Very close to beach shops and restaurants Beautiful suite with kitchens."
Canada
Mary
$283 nightly
The price is $320
May 20 - May 21
Total with taxes and fees
Bridgewalk Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,251 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
$217 nightly
The price is $243
May 21 - May 22
Total with taxes and fees
Captiva Beach Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (366 reviews)
"Cute place perfect for our holiday beach stay."
United States
Shelly
$208 nightly
The price is $235
May 18 - May 19
Total with taxes and fees
Tiny House Siesta

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, (450 reviews)
"Great location, clean and quiet. "
United States
Sara
$206 nightly
The price is $233
May 18 - May 19
Total with taxes and fees
Haley's at The Anna Maria Island Inn

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
$535 nightly
The price is $575
Jun 3 - Jun 4
Total with taxes and fees
Chadwick Cove Resort & Marina

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (274 reviews)
"Great place"
United States
tony
$221 nightly
The price is $250
May 19 - May 20
Total with taxes and fees
Casey Key Resort - Gulf Shores

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, (403 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
$270 nightly
The price is $305
May 26 - May 27
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
$298 nightly
The price is $337
May 18 - May 19
Total with taxes and fees
Cedar Run Resort - Roam Hospitality

4 Mi to Siesta Key Beach: Condo w/ Private Patio

4 Mi to Siesta Key Beach: Condo w/ Private Patio
3.5 star property
Sarasota
$303 nightly
The price is $339
Jun 13 - Jun 14
Total with taxes and fees
4 Mi to Siesta Key Beach: Condo w/ Private Patio

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$896 nightly
The price is $973
May 30 - May 31
Total with taxes and fees
Gulf View Condominiums

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (126 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
$269 nightly
The price is $304
May 27 - May 28
Total with taxes and fees
SeaSpray Resort

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (173 reviews)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveler
$636 nightly
The price is $699
May 19 - May 20
Total with taxes and fees
Palm Tree Villas

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
$333 nightly
The price is $376
May 20 - May 21
Total with taxes and fees
Siesta Key Island Rentals

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$292 nightly
The price is $330
May 19 - May 20
Total with taxes and fees
Siesta Heron Suites & Villas

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
$375 nightly
The price is $424
May 20 - May 21
Total with taxes and fees
The Inn On Siesta Key
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

Find out more about Legacy Trail

Everything you need to know about Legacy Trail vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Legacy Trail vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Legacy Trail vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Legacy Trail. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Legacy Trail in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Legacy Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Legacy Trail vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Legacy Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.