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Featured Cottages in Legacy Trail

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The Inn On Siesta Key

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

9.2 out of 10, Wonderful, (60)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is AU$738
includes taxes & fees
9 Aug - 10 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (94)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

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

9.2 out of 10, Wonderful, (94)
"We have stayed at this cottage before- just love this beach."
The price is AU$668
includes taxes & fees
13 Aug - 14 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (11)
"This cottage was the perfect anniversary getaway. Centrally located and easy to visit the beaches and explore the island on the provided golfcart"
Anna Maria Cottage with Golf Cart

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, (125)
"We had an awesome vacation! The house beach and pool were outstanding. Hope to return next year!!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (135)
"Our stay was great. Everything was as advertised and expected. "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

The Cottage by Anna Maria Island

9.8 out of 10, Exceptional, (12)
"Great host ,nice property. We had a problem with the shower, but the host had it fixed almost immediately. Would definitely stay here again."
The Cottage by Anna Maria Island

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"We were extremely happy with our stay and Evan as our host. He went out of his way to make sure everything went smoothly including helping us find all the beach amenities. The house was excellent and just what we needed, just a short walk across the road to the beach. We would definitely stay here again!"
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is AU$787
includes taxes & fees
12 Aug - 13 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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

9.8 out of 10, Exceptional, (280)
"Beautiful home and great location. Close to the beach, food and ice cream. Will definitely stay here again. Host was really responsive. "
Charming cottage in quiet area, close to beach & bay.

Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

9.6 out of 10, Exceptional, (23)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

10.0 out of 10, Exceptional, (71)
"Wonderful quiet neighborhood property with very attentive property owners. Flamingo Cottage is ideally located for easy access to the beach as well as Shopping within walking distance. We look forward to our return next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

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

9.8 out of 10, Exceptional, (23)
"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

1-bedroom cottage just 10 minutes from Siesta Key Beach

9.0 out of 10, Wonderful, (36)
"We greatly enjoyed our stay. The yard is very secluded and quite large, which was ideal for us. The house was exceptionally clean, and is well laid out. Powerful a/c system, super welcome for hot florida days. It also has a very large screened in lanai, which is perfect for relaxing. "
1-bedroom cottage just 10 minutes from Siesta Key Beach

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.0 out of 10, Wonderful, (8)
"Great location. Very clean and well maintained. I would come back "
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

12 Mi to Beach: Home w/ Patio & Yard in Bradenton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Clean & close to the convention center"
12 Mi to Beach: Home w/ Patio & Yard in Bradenton

Blue Isle Oasis: Adorable, updated 2 bedroom cottage

9.0 out of 10, Wonderful, (2)
"Nicely renovated interior and exterior. "
Blue Isle Oasis: Adorable, updated 2 bedroom cottage

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "
Country Cottage Home

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

9.8 out of 10, Exceptional, (76)
"My granddaughters thought the cottage was charming, and enjoyed staying there."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
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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