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, (266 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
$127 nightly
The price is $143
May 4 - May 5
Total with taxes and fees
Kon Tiki Inn

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
$132 nightly
The price is $149
Apr 27 - Apr 28
Total with taxes and fees
Venice Beach Villas

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,399 reviews)
"Love the location, excellent service and place clean and quite "
United States
Dayami
$226 nightly
The price is $256
Apr 12 - Apr 13
Total with taxes and fees
Tropical Beach Resorts

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (619 reviews)
"Love this place"
United States
Marialis
$189 nightly
The price is $214
May 3 - May 4
Total with taxes and fees
A Beach Retreat

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,275 reviews)
"Clean room, quiet and in a location convenient to Siesta Key. The pool is very nice, although located at the front of the property alongside a busy road. Would definitely recommend this hotel, especially if a kitchenette is desired."
United States
CAROLYN
$179 nightly
The price is $202
Apr 19 - Apr 20
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (245 reviews)
"Staff very accommodating."
United States
Genevieve
$204 nightly
The price is $230
Apr 22 - Apr 23
Total with taxes and fees
Tropical Villas of Venice Beach

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (788 reviews)
"So nice to walk to restaurants and shops. Very walkable. Clean. Updated and relaxing atmosphere. Parking was really convenient and accessible. Would stay again."
United States
Deborah
$318 nightly
The price is $359
Apr 16 - Apr 17
Total with taxes and fees
Bridgewalk Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (362 reviews)
"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "
United States
Adanna
$195 nightly
The price is $220
Apr 27 - Apr 28
Total with taxes and fees
Tiny House Siesta

Coastal 2-Bedroom Home Minutes to Beach

Coastal 2-Bedroom Home Minutes to Beach
3.0 star property
Englewood Central
10.0 out of 10, Exceptional, (3 reviews)
"Great space- had everything needed to enjoy a beach stay"
United States
Adriana
$373 nightly
The price is $421
Apr 10 - Apr 11
Total with taxes and fees
Coastal 2-Bedroom Home Minutes to Beach

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
$309 nightly
The price is $345
Apr 19 - Apr 20
Total with taxes and fees
4 Mi to Siesta Key Beach: Condo w/ Private Patio

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, (442 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
$304 nightly
The price is $343
May 5 - May 6
Total with taxes and fees
Haley's at The Anna Maria Island Inn

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, (388 reviews)
"Love this place "
United States
Leeanne
$302 nightly
The price is $341
May 5 - May 6
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,224 reviews)
"Clean and very close to beach. "
United States
Daniel
$251 nightly
The price is $281
Apr 12 - Apr 13
Total with taxes and fees
Captiva Beach Resort

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (64 reviews)
"We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars! "
United States
Laura
$406 nightly
The price is $459
Apr 20 - Apr 21
Total with taxes and fees
Siesta Key Island Rentals

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (272 reviews)
"Great place"
United States
tony
$219 nightly
The price is $247
May 3 - May 4
Total with taxes and fees
Casey Key Resort - Gulf Shores

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$896 nightly
The price is $973
Apr 15 - Apr 16
Total with taxes and fees
Gulf View Condominiums

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (41 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$318 nightly
The price is $360
Apr 28 - Apr 29
Total with taxes and fees
Siesta Heron Suites & Villas

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
$324 nightly
The price is $363
Apr 14 - Apr 15
Total with taxes and fees
Chadwick Cove Resort & Marina

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
$356 nightly
The price is $402
Apr 9 - Apr 10
Total with taxes and fees
The Inn On Siesta Key

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (105 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
$278 nightly
The price is $314
May 3 - May 4
Total with taxes and fees
SeaSpray Resort
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 $165 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.