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1 Aug - 3 Aug
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8 Aug - 10 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Browse Select Legacy Trail Apartments

Seabreeze at Anna Maria Island Inn
Exterior

Seabreeze at Anna Maria Island Inn

3.0 star property
8.8 out of 10, Excellent, (23)
"Great location"
Seabreeze at Anna Maria Island Inn
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (315)
"Excellent property, excellent communication with Susan, i recommend it to anyone who wants to have an amazing vacation."
The Ringling Beach House
Pelican Post at Anna Maria Island Inn
Exterior

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (285)
"This was an amazing property and we can’t wait to come back on our next trip to the island."
Pelican Post at Anna Maria Island Inn
Sea Club I Beach Resort
On the beach, white sand

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
Deluxe Studio, Bay View | View from room

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
Apartment (2 Bedrooms) | Interior

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

3.0 star property
9.6 out of 10, Exceptional, (14)
"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
Beach nearby, white sand, sun-loungers, beach towels

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
Beach nearby, white sand, beach umbrellas, beach towels

Palm Tree Villas

3.0 star property
9.2 out of 10, Wonderful, (169)
"Unbelievable value! Location was perfect and so were the amenities and the cleanliness of the unit. Our 5-6 time staying at AMI and the first unit we would stay at again. We will return to this place again and again. "
Palm Tree Villas
Casa Limonada Boutique Motel
On the beach, white sand, beach umbrellas, beach towels

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!
Apartment (2 Bedrooms) | 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
Apartment (2 Bedrooms) | 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
Apartment (0 Bedroom) | 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!
Apartment (2 Bedrooms) | Interior

Welcoming Sarasota Vacation Rental w/ Pool!

3.0 star property
10.0 out of 10, Exceptional, (1)
"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
Property entrance

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!
Apartment (0 Bedroom) | 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
Apartment (2 Bedrooms) | 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
Apartment | Iron/ironing board

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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"It was an excellent choice, conveniently close to the beach, stores, shops and restaurants"
Nubia 3-night trip
Posted 1 day ago
Spark by Hilton Sarasota Siesta Key Gateway