Legacy Trail Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Legacy Trail vacation rentals

Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5194)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
$164 nightly
The price is $185
Jan 6 - Jan 7
Total with taxes and fees
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun 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, (2226)
"Very nice place !"
United States
Ivette
$130 nightly
The price is $147
Jan 6 - Jan 7
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
$308 nightly
The price is $349
Jan 13 - Jan 14
Total with taxes and fees
Siesta Heron Suites & Villas
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, (336)
"Easy access to Bridge St... Walk quick to beach. Quiet pool nice ... They can definitely improve the Internet as that was spotty. "
United States
Marc
$189 nightly
The price is $214
Jan 6 - Jan 7
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Exterior
Seabreeze at Anna Maria Island Inn

Apartment in Bradenton Beach

Seabreeze at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (66)
"Very great stay will stay again "
United States
Joseph
$201 nightly
The price is $227
Jan 6 - Jan 7
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
Fridge, microwave, stovetop, coffee/tea maker
Charming cottage for 2 across warm mineral springs park

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
$145 nightly
The price is $161
Jan 6 - Jan 7
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (249)
"Great place! "
United States
Michelle
$211 nightly
The price is $238
Jan 6 - Jan 7
Total with taxes and fees
Kon Tiki Inn
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, (306)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$452 nightly
The price is $511
Feb 5 - Feb 6
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen
Siesta Key Island Rentals

Vacation Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (55)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$275 nightly
The price is $311
Jan 6 - Jan 7
Total with taxes and fees
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, (583)
"Great location, recent updates"
United States
Michael
$184 nightly
The price is $208
Jan 6 - Jan 7
Total with taxes and fees
A Beach Retreat
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, (1184)
"Excellent place and location, "
United States
Richard
$223 nightly
The price is $250
Jan 6 - Jan 7
Total with taxes and fees
Captiva Beach Resort
Deluxe Suite, 2 Bedrooms | Living area | TV
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (84)
"Very clean very quiet and a great location to the beach."
United States
Dave
$275 nightly
The price is $311
Jan 7 - Jan 8
Total with taxes and fees
SeaSpray Resort
Property grounds
Chadwick Cove Resort & Marina

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
$488 nightly
The price is $522
Jan 6 - Jan 7
Total with taxes and fees
Chadwick Cove Resort & Marina
Property grounds
Old Floridian cottage in Historic Gulf Village

Vacation Home in Olde Englewood Village

Old Floridian cottage in Historic Gulf Village
9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
$280 nightly
The price is $312
Jan 11 - Jan 12
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
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 traveler
$654 nightly
The price is $720
Jan 6 - Jan 7
Total with taxes and fees
Palm Tree Villas
Outdoor pool, pool umbrellas, sun loungers
Bridgewalk Resort

Aparthotel in Bridge Street

Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (770)
"The staff was very courteous, friendly and helpful."
United States
Edward
$230 nightly
The price is $260
Jan 20 - Jan 21
Total with taxes and fees
Bridgewalk Resort
Fridge, microwave, coffee/tea maker, dining tables
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Apartment in Bayshore Gardens

Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
9.2 out of 10, Wonderful, (36)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
$155 nightly
The price is $173
Jan 17 - Jan 18
Total with taxes and fees
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Terrace/patio
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Vacation Home in Bradenton

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
9.4 out of 10, Exceptional, (67)
"Great place to stay!"
United States
Wendi B.
$140 nightly
The price is $156
Jan 6 - Jan 7
Total with taxes and fees
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Terrace/patio
The Hideaways at Point Pleasant (Palm Side)

Vacation Home in Bradenton

The Hideaways at Point Pleasant (Palm Side)
10.0 out of 10, Exceptional, (169)
"perfect location and size for what we were looking for"
United States
michael w.
$251 nightly
The price is $258
Jan 6 - Jan 7
Total with taxes and fees
The Hideaways at Point Pleasant (Palm Side)
Property grounds
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Vacation Home in Sabal Harbour

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
2.0 star property
10.0 out of 10, Exceptional, (21)
"Everything was great!"
United States
Lisa and Colin M.
$310 nightly
The price is $345
Jan 6 - Jan 7
Total with taxes and fees
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
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

Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

10/10 Excellent
"We had a short but very pleasant stay at the Compass Hotel by Margaritaville. Our room had a lovely water view, and the entire property is beautifully maintained. A relaxing and enjoyable stop, would happily return."
CHRISTINE 2-night trip
Posted 2 days ago
Compass Hotel by Margaritaville Anna Maria Sound

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.

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