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 21 - May 22
Total with taxes and fees
Kon Tiki 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
$500 nightly
The price is $536
May 28 - May 29
Total with taxes and fees
Chadwick Cove Resort & Marina

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (67 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
$326 nightly
The price is $368
May 20 - May 21
Total with taxes and fees
Siesta Key Island Rentals

Path to Paradise.

Path to Paradise.
Olde Englewood Village
$233 nightly
The price is $260
May 20 - May 21
Total with taxes and fees
Path to Paradise.

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (480 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

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (66 reviews)
"Short stay to see a friend that was in the area it was a great olace"
United States
deborah f.
$189 nightly
The price is $211
May 20 - May 21
Total with taxes and fees
The "Grouper"

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$195 nightly
The price is $218
May 24 - May 25
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.

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 20 - May 21
Total with taxes and fees
Haley's at The Anna Maria Island Inn

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (127 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
$287 nightly
The price is $324
Jun 18 - Jun 19
Total with taxes and fees
SeaSpray Resort

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (24 reviews)
"Great little place! Wish we could have spent more time"
United States
Tricia W.
$130 nightly
The price is $144
May 20 - May 21
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,494 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 20 - May 21
Total with taxes and fees
Tropical Beach Resorts

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,255 reviews)
"Nice place for a relaxing time"
United States
Andres Eduardo
$223 nightly
The price is $249
May 20 - May 21
Total with taxes and fees
Captiva Beach Resort

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Englewood
10.0 out of 10, Exceptional, (57 reviews)
"Great stay at Pura Vida! The host is amazing very attentive to your needs. The place was perfect! Beautifully decorated and super clean! "
United States
Lisa D.
$269 nightly
The price is $298
May 20 - May 21
Total with taxes and fees
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (65 reviews)
"A fabulous place that was super easy to check in and all communication with the host was prompt. Very relaxing atmosphere"
United States
Tara
$270 nightly
The price is $299
May 21 - May 22
Total with taxes and fees
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Bradenton Beach
10.0 out of 10, Exceptional, (20 reviews)
"Great location perfect room for 2 people. "
United States
Macey
$273 nightly
The price is $304
May 20 - May 21
Total with taxes and fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.2 out of 10, Wonderful, (77 reviews)
"Great place to stay!"
United States
Wendi B.
$166 nightly
The price is $185
May 20 - May 21
Total with taxes and fees
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

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 27 - May 28
Total with taxes and fees
A Beach Retreat

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
$300 nightly
The price is $335
May 20 - May 21
Total with taxes and fees
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (75 reviews)
"Great location in Siesta Key Village, can walk to all the shops and restaurants as well as the beach "
United States
Erica S.
$375 nightly
The price is $406
May 25 - May 26
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!

"Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (32 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
$326 nightly
The price is $364
May 20 - May 21
Total with taxes and fees
"Stingray" 3 miles to Anna Marie
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.