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Aug 8 - Aug 10
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Featured Apartments in Legacy Trail

Seabreeze at Anna Maria Island Inn
Enjoy ocean views from this deck with tables and chairs under umbrellas, surrounded by a railing.

Seabreeze at Anna Maria Island Inn

3.0 star property
8.8 out of 10, Excellent, (24)
"Great location"
The price is P15,761
P19,947 total
includes taxes & fees
Sep 1 - Sep 2
Seabreeze at Anna Maria Island Inn
The Ringling Beach House
Classic hotel with a symmetrical facade, central entrance, and upper-level balcony.

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (317)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Pelican Post at Anna Maria Island Inn
Stunning building with a distinctive roof and lush tropical surroundings.

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (287)
"This was an amazing property and we can’t wait to come back on our next trip to the island."
The price is P12,320
P15,592 total
includes taxes & fees
Sep 1 - Sep 2
Pelican Post at Anna Maria Island Inn
Sea Club I Beach Resort
Relax in style with comfortable lounge chairs overlooking the ocean.

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (318)
"Nice place "
Sea Club I Beach Resort
Casey Key Resort - Gulf Shores
Enjoy the serene view of the water from the comfort of your room, featuring a large window, wicker chairs, and a small table with a lamp.

Casey Key Resort - Gulf Shores

3.0 star property
8.4 out of 10, Very Good, (259)
"Cheryl was an amazing host :)"
Casey Key Resort - Gulf Shores
Condo w/ Pool Access < 4 Miles to Siesta Key Beach
Interior

Condo w/ Pool Access < 4 Miles to Siesta Key Beach

3.0 star property
9.6 out of 10, Exceptional, (15)
"Very clean condo and easy to find. Would definitely stay here again. "
Condo w/ Pool Access < 4 Miles to Siesta Key Beach
Haley's at The Anna Maria Island Inn
Enjoy access to the public beach from this property.

Haley's at The Anna Maria Island Inn

3.0 star property
8.6 out of 10, Excellent, (373)
"It was a great stay"
Haley's at The Anna Maria Island Inn
Palm Tree Villas
Experience the serene beach atmosphere, where waves gently lap onto the shore.

Palm Tree Villas

3.0 star property
9.2 out of 10, Wonderful, (169)
"Lovely property, clean and so close to the beach! Do need a car, for food/dinning. We'll be back."
Palm Tree Villas
Casa Limonada Boutique Motel
Guests can relax on the beach under a shaded umbrella.

Casa Limonada Boutique Motel

3.5 star property
10.0 out of 10, Exceptional, (9)
"It was so clean and cute! All the feels!"
Casa Limonada Boutique Motel
Fish, Relax & Repeat: Palmetto Unit w/ Patio!
Interior

Fish, Relax & Repeat: Palmetto Unit w/ Patio!

3.0 star property
10.0 out of 10, Exceptional, (4)
"Was an amazing stay! Will come again. Everything was nice and comfortable. "
Fish, Relax & Repeat: Palmetto Unit w/ Patio!
Walk to Beach: Tropical Retreat in Anna Maria
Interior

Walk to Beach: Tropical Retreat in Anna Maria

3.5 star property
Walk to Beach: Tropical Retreat in Anna Maria
Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach
Interior

Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach

3.0 star property
Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach
Welcoming Sarasota Vacation Rental w/ Pool!
Interior

Welcoming Sarasota Vacation Rental w/ Pool!

3.0 star property
10.0 out of 10, Exceptional, (2)
"everything you could need to enjoy a home away from home was there. Although the master bed had a bad squeak every time you moved or rolled over,"
Welcoming Sarasota Vacation Rental w/ Pool!
Shorewalk Vacation Villas
Stroll through the beautifully landscaped Shorewalk area, surrounded by neatly trimmed bushes and a variety of plants.

Shorewalk Vacation Villas

2.0 star property
8.8 out of 10, Excellent, (712)
"Highly recommend 👌 location, community is beautiful 😍 "
Shorewalk Vacation Villas
Remodeled Siesta Key Studio Near Beach!
Front of property

Remodeled Siesta Key Studio Near Beach!

3.0 star property
Remodeled Siesta Key Studio Near Beach!
Walk to Shore: Condo w/ Pool Access in Siesta Key
Interior

Walk to Shore: Condo w/ Pool Access in Siesta Key

3.0 star property
Walk to Shore: Condo w/ Pool Access in Siesta Key
Anna Maria Island Bay Watch Bungalow
Relax on the beach with umbrellas and sun loungers at our seaside resort.

Anna Maria Island Bay Watch Bungalow

3.5 star property
Anna Maria Island Bay Watch Bungalow
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
"Me encamto el hotel muy limpio personas muy amables y atentas la comida muy buena,la piscina, en realidad un muy buen hotel,tranquilo y cerca de las mejores playas."
Yanely 3-night trip
Posted 1 day ago
Compass Hotel by Margaritaville Anna Maria Sound