Legacy Trail Vacation Rentals

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Vacation Rentals in Legacy Trail

Our top choices for Legacy Trail vacation rentals

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4922)
"Wonderful resort "
$159 nightly
The price is $180
Sep 1 - Sep 2
Total with taxes and fees
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2166)
"Bed comfort , great location, friendly staff. "
$136 nightly
The price is $154
Sep 1 - Sep 2
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (27)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
$209 nightly
The price is $236
Sep 1 - Sep 2
Total with taxes and fees
SeaSpray Resort

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (298)
"Place was very clean and perfect location for the beach/surrounding restaurants."
$223 nightly
The price is $252
Sep 1 - Sep 2
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (319)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
$225 nightly
The price is $255
Sep 1 - Sep 2
Total with taxes and fees
The Ringling Beach House

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (33)
"Awesome place to stay "
$246 nightly
The price is $278
Sep 3 - Sep 4
Total with taxes and fees
Seabreeze at Anna Maria Island Inn

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1124)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
$182 nightly
The price is $203
Sep 1 - Sep 2
Total with taxes and fees
Captiva Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (317)
"Super helpful staff."
$130 nightly
The price is $147
Sep 3 - Sep 4
Total with taxes and fees
Tiny House Siesta

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (738)
"Very nice rooms and location "
$273 nightly
The price is $309
Sep 9 - Sep 10
Total with taxes and fees
Bridgewalk Resort

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (227)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
Kon Tiki Inn

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (126)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (430)
"Outstanding stay. Great room and amenities with a great locatio. We will return!! "
Venice Beach Villas

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (4)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
$270 nightly
The price is $305
Sep 2 - Sep 3
Total with taxes and fees
Siesta Key Island Rentals

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (382)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (284)
"Great location. Everyone was very friendly and accommodating!"
$417 nightly
The price is $471
Sep 29 - Sep 30
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
$275 nightly
The price is $311
Sep 1 - Sep 2
Total with taxes and fees
The Inn On Siesta Key
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Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

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 $147 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.