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

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5192)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
$164 nightly
The price is $185
Jan 4 - Jan 5
Total with taxes and fees
Tropical Beach Resorts
Exterior
Kon Tiki Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (249)
"Was close to the beach! Enjoyed having the little kitchen. Very quiet. Would definitely stay again."
United States
Linda
$205 nightly
The price is $232
Jan 14 - Jan 15
Total with taxes and fees
Kon Tiki Inn
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (304)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$441 nightly
The price is $498
Feb 3 - Feb 4
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2224)
"Very nice place !"
United States
Ivette
$136 nightly
The price is $154
Jan 4 - Jan 5
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Exterior
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (335)
"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
$201 nightly
The price is $227
Jan 4 - Jan 5
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
$208 nightly
The price is $235
Jan 6 - Jan 7
Total with taxes and fees
Tiny House Siesta
On the beach, white sand
A Beach Retreat

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (581)
"Great location, recent updates"
United States
Michael
$184 nightly
The price is $208
Jan 4 - Jan 5
Total with taxes and fees
A Beach Retreat
Beach nearby, white sand, sun loungers, beach towels
Haley's at The Anna Maria Island Inn

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, (405)
"Beautiful location. Walking distance to beach. "
United States
Maria
$136 nightly
The price is $154
Jan 4 - Jan 5
Total with taxes and fees
Haley's at The Anna Maria Island Inn
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
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
Outdoor pool, pool umbrellas, sun loungers
Bridgewalk Resort

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
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
Deluxe Studio, Bay View | View from room
Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (267)
"Very helpful and nice staff. Lovely room, great location. Adorable cottage"
United States
Hilary
$372 nightly
The price is $420
Jan 4 - Jan 5
Total with taxes and fees
Casey Key Resort - Gulf Shores
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen
Siesta Key Island Rentals

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (55)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$303 nightly
The price is $342
Jan 6 - Jan 7
Total with taxes and fees
Siesta Key Island Rentals
Exterior
Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (66)
"Very great stay will stay again "
United States
Joseph
$201 nightly
The price is $227
Jan 5 - Jan 6
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
Property grounds
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
$486 nightly
The price is $521
Jan 4 - Jan 5
Total with taxes and fees
Chadwick Cove Resort & Marina
Beach nearby, white sand, beach umbrellas, beach towels
Palm Tree Villas

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
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 5 - Jan 6
Total with taxes and fees
Palm Tree Villas
Deluxe Suite, 2 Bedrooms | Living area | TV
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
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
Exterior
Coastal Breeze Siesta - Turtle

Coastal Breeze Siesta - Turtle

Coastal Breeze Siesta - Turtle
2.0 star property
Siesta Key
10.0 out of 10, Exceptional, (1)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
$372 nightly
The price is $419
Jan 18 - Jan 19
Total with taxes and fees
Coastal Breeze Siesta - Turtle
Outdoor pool
Alamanda Villas

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.6 out of 10, Exceptional, (4)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
$426 nightly
The price is $460
Jan 4 - Jan 5
Total with taxes and fees
Alamanda Villas
House | 3 bedrooms
Sleeps 8 Pets Welcome Fenced In Backyard

Sleeps 8 Pets Welcome Fenced In Backyard

Sleeps 8 Pets Welcome Fenced In Backyard
2.0 star property
Southgate
$267 nightly
The price is $301
Jan 6 - Jan 7
Total with taxes and fees
Sleeps 8 Pets Welcome Fenced In Backyard
Exterior
Gulf View Condominiums

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$788 nightly
The price is $852
Jan 4 - Jan 5
Total with taxes and fees
Gulf View Condominiums
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 15 hours 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 $154 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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