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, (264 reviews)
"Very nice rooms and close to everything. Owner is very welcoming."
United States
Jennifer
The price is CA $225
CA $255 total
includes taxes & fees
Apr 21 - Apr 22
Kon Tiki Inn

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (103 reviews)
"VERY ENJOYABLE /STAFF WAS EXCELLENT"
United States
KARL
The price is CA $522
CA $589 total
includes taxes & fees
Apr 19 - Apr 20
SeaSpray Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,216 reviews)
"Room was clean and well stocked. Staff were easy to access and helpful. Location was great!"
United States
Daniel
The price is CA $346
CA $415 total
includes taxes & fees
Apr 19 - Apr 20
Captiva Beach Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,379 reviews)
"We had a very nice time and the resort was centrally located and right down the road from the beach. "
United States
Christopher Kevin
The price is CA $281
CA $353 total
includes taxes & fees
Apr 12 - Apr 13
Tropical Beach Resorts

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
Venice Beach Villas

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (612 reviews)
"Literally steps to the beach. "
United States
william
A Beach Retreat

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (89 reviews)
"The view was beautiful! "
United States
Jennifer
The price is CA $434
CA $550 total
includes taxes & fees
Apr 20 - Apr 21
Seabreeze at 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, (441 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
The price is CA $488
CA $618 total
includes taxes & fees
Apr 16 - Apr 17
Haley's at The Anna Maria Island Inn

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
The price is CA $353
CA $399 total
includes taxes & fees
Apr 22 - Apr 23
Bridgewalk Resort

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
The price is CA $228
CA $288 total
includes taxes & fees
Apr 22 - Apr 23
Tropical Villas of Venice Beach

Christian Retreat Conference Center

Christian Retreat Conference Center
3.0 star property
Bradenton
8.8 out of 10, Excellent, (8 reviews)
"A bargain given the cost of other hotels. Nice being hosted by Christians!"
United States
Patrick
The price is CA $139
CA $158 total
includes taxes & fees
Apr 19 - Apr 20
Christian Retreat Conference Center

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,272 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
The price is CA $245
CA $277 total
includes taxes & fees
Apr 16 - Apr 17
Hibiscus Suites - Gateway to Siesta Key

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (356 reviews)
"Nice beach house center to town and the Main Beach. Beach access across street as well. "
United States
Timothy
The Ringling Beach House

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, (381 reviews)
"Love this place "
United States
Leeanne
The price is CA $335
CA $424 total
includes taxes & fees
Apr 12 - Apr 13
Pelican Post at Anna Maria Island Inn

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
Siesta Key Island Rentals

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (195 reviews)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is CA $552
CA $1,376 total
includes taxes & fees
Apr 15 - Apr 16
Gulf View Condominiums

Minorga on the Gulf

Minorga on the Gulf
3.0 star property
Siesta Key Village
The price is CA $786
CA $1,300 total
includes taxes & fees
Apr 3 - Apr 4
Minorga on the Gulf

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (269 reviews)
"Very helpful and nice staff. Lovely room, great location. Adorable cottage"
United States
Hilary
Casey Key Resort - Gulf Shores

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
The price is CA $327
CA $648 total
includes taxes & fees
Apr 26 - Apr 27
Siesta Heron Suites & Villas
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Legacy Trail. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.