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Featured Cottages in Legacy Trail

Our top choices for Legacy Trail cottages

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The price is AU$544
includes taxes & fees
23 Aug - 24 Aug
The Inn On Siesta Key

Port Charlotte Home w/ Pool - 8 Mi to Beaches!

3.0 star property
9.4 out of 10, Exceptional, (3)
"Everything was clean and comfortable. We will be booking again!!!"
The price is AU$642
includes taxes & fees
23 Aug - 24 Aug
Port Charlotte Home w/ Pool - 8 Mi to Beaches!

The "Grouper"

9.6 out of 10, Exceptional, (31)
"Great location."
The price is AU$332
includes taxes & fees
29 Aug - 30 Aug
The "Grouper"

Romantic Island Getaway Just Steps from the Beach

2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
The price is AU$597
includes taxes & fees
23 Aug - 24 Aug
Romantic Island Getaway Just Steps from the Beach

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (77)
"Its right next to everything we needed"
The price is AU$477
includes taxes & fees
27 Aug - 28 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

8.0 out of 10, Very good, (1)
"Beautiful decor, perfect location to the beach (5min walking). very thoughtful touches throughout the rental. The kitchen is well- equipped with all you need. Bedroom with excellent mattress. The patio with BBQ, kayaks, free parking, beach chair /loungers available, the property was immaculate.10/10. I would recommend""
The price is AU$785
includes taxes & fees
31 Aug - 1 Sept
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

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

9.2 out of 10, Wonderful, (95)
"We have stayed at this cottage before- just love this beach."
The price is AU$677
includes taxes & fees
24 Aug - 25 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

7mi to Anna Maria Newly Renovated Private Cottage

The price is AU$392
includes taxes & fees
29 Aug - 30 Aug
7mi to Anna Maria Newly Renovated Private Cottage

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
The price is AU$800
includes taxes & fees
24 Aug - 25 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

The price is AU$805
includes taxes & fees
24 Aug - 25 Aug
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (32)
"Fun stay, great location"
The price is AU$386
includes taxes & fees
24 Aug - 25 Aug
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Private King Bed Suite-Near AMI Beach-Walk D’Town.

9.6 out of 10, Exceptional, (36)
"The Sea Horse Cottage and Bradenton area were charming and beautiful....we had a nice time!!"
The price is AU$521
includes taxes & fees
30 Aug - 31 Aug
Private King Bed Suite-Near AMI Beach-Walk D’Town.

5 star Guest House heated pool on the water!

The price is AU$801
includes taxes & fees
23 Aug - 24 Aug
5 star Guest House heated pool on the water!

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
The price is AU$713
includes taxes & fees
25 Aug - 26 Aug
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Nest Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
Nest Cottage Across street from beach and Heated Pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (39)
"This property definitely did not disappoint! Fantastic location that’s close to both the beach and the pier. Shops and food are all within walking distance. The backyard was a hit. The pool and putting green were a fun addition to the large backyard space. Great communication from the hosts who made sure our check in process went well and called to make sure everything was going well and to let them know if we needed anything. Would definitely stay at this space again. "
The price is AU$865
includes taxes & fees
25 Aug - 26 Aug
Adorable Cottage with Covered Balconies and Private Pool

Beautiful Guest House Near the Beach with Private Pool!

8.4 out of 10, Very good, (26)
"The space directly above the local taco and donut shops was exactly as advertised! Clean, quaint, and perfect for our family of 5 that took full advantage of the private pool and 1 block walk to the beach. Can't wait to come back!!"
The price is AU$788
includes taxes & fees
26 Aug - 27 Aug
Beautiful Guest House Near the Beach with Private Pool!

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

9.2 out of 10, Wonderful, (60)
"We loved this little cottage and will absolutely go back in the future. Thank you so much for a wonderful retreat. "
The price is AU$717
includes taxes & fees
24 Aug - 25 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
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