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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 45 Cottages in Legacy Trail with updated reviews, rates, and availability.

The Inn On Siesta Key
The Cabana, 2 Bedroom 2 Bath (1 King, 2 Twins) | Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (175)
"Outstanding service. Room and facility was very clean. Staff is amazing. We would strongly recommend The Inn and we plan on returning for our next vacation "
The price is AED 651
AED 872 total
includes taxes & fees
14 May - 15 May
The Inn On Siesta Key
The "Grouper"
Beach

The "Grouper"

9.6 out of 10, Exceptional, (28)
"Great location."
The price is AED 364
AED 775 total
includes taxes & fees
18 May - 19 May
The "Grouper"
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (54)
"Really enjoyed our stay. Location is excellent."
The price is AED 1,095
AED 2,230 total
includes taxes & fees
13 May - 14 May
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (172)
"It was a quiet place we ended up not going very many places."
The price is AED 731
AED 2,081 total
includes taxes & fees
15 May - 16 May
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Sun loungers, beach towels

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

10.0 out of 10, Exceptional, (1)
"This was perfect for our family. It was a quick walk to the beach. We loved it!"
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (87)
"Amazing location of property, right on the beautiful beach. Plenty of parking, good restaurants nearby. We will be back "
The price is AED 1,646
AED 2,843 total
includes taxes & fees
13 May - 14 May
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Charming cottage in quiet area, close to beach & bay.
Sun loungers, beach towels

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (270)
"Lovely clean little cottage. Walkable to a lot. We really enjoyed the place and a very accommodating host! "
Charming cottage in quiet area, close to beach & bay.
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Sun loungers

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (19)
"We had an amazing time at Sophie’s Cottage. We lucked out and got a renovated home due to the Hurricanes. The proximity to the beach and town are great. Short bike ride to both. Jim, the owner, helped us immediately with any issues. Our kids caught snappers, catfish, jacks, sting rays and needle fish off of the dock of the home. Great time, great home, great location!!! "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Across The Street From #1 Beach
Beach nearby, sun loungers, beach towels

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Great accommodations, great location."
Across The Street From #1 Beach
Tropical Paradise On The Beach Permit VRC17-000168
Fridge, microwave, oven, stovetop

Tropical Paradise On The Beach Permit VRC17-000168

9.2 out of 10, Wonderful, (129)
"Good, clean accomodations, including washer and dryer. Excellent access to the beach!"
Tropical Paradise On The Beach Permit VRC17-000168
The Cottage by Anna Maria Island
Beach

The Cottage by Anna Maria Island

9.6 out of 10, Exceptional, (10)
"Thank you for a lovely stay!"
The Cottage by Anna Maria Island
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Property grounds

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (186)
"We were actually at a property in Venice Beach, a house with private pool. It was very nicely decorated and so comfortable. Close to everything. We had a blast."
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Beach nearby

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

10.0 out of 10, Exceptional, (2)
"The property was very nice and clean. It's also in a great location - very close to the beach and the Village. I will definitely stay here again."
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Mermaid Cottage
Beach

Mermaid Cottage

10.0 out of 10, Exceptional, (12)
"Loved the decor and separate spaces. Liked that there was everything needed to prepare meals there. Nice stay."
Mermaid Cottage
Charming cottage for 2 across warm mineral springs park
Fridge, microwave, stovetop, coffee/tea maker

Charming cottage for 2 across warm mineral springs park

9.0 out of 10, Wonderful, (7)
"I'm currently working in the area and this place made it even easier being away from home I've enjoyed the area and the place "
Charming cottage for 2 across warm mineral springs park
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Terrace/patio

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
The price is AED 1,388
AED 3,765 total
includes taxes & fees
20 May - 21 May
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

8.8 out of 10, Excellent, (73)
"Property is one house away from beach access on a very quiet street. Walking distance to great spots. Pool and screened in patio were our favorite spots. They also had beach chairs and sand toys which was an added bonus."
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
On the beach

Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

10.0 out of 10, Exceptional, (19)
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
On the beach, sun loungers, beach towels

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (118)
"We enjoyed our stay. It is perfect for families and the location is perfect!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

8.6 out of 10, Excellent, (4)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lots of beach time"
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
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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Other property types in Legacy Trail

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4649)
"Amazing trip and stay!!!"
The price is AED 492
AED 639 total
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2123)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is AED 553
AED 625 total
includes taxes & fees
13 May - 14 May
Hibiscus Suites - Gateway to Siesta Key
Anna Maria Beach Resort
On the beach, white sand, beach towels

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (202)
"This is a very good place to have relaxed days. The room was perfect, with all that we needed. The view was perfect. All the amenities help to have fun."
The price is AED 1,946
AED 2,463 total
includes taxes & fees
13 May - 14 May
Anna Maria Beach 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.