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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Legacy Trail and around

The Inn On Siesta Key
Enjoy the serene view from this balcony with a wicker chair and table.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The price is €274
includes taxes & fees
27 Jul - 28 Jul
The Inn On Siesta Key
Tropical Paradise On The Beach Permit VRC17-000168
Enjoy the ocean view from the deck, with access to the beach via a paved pathway.

Tropical Paradise On The Beach Permit VRC17-000168

9.4 out of 10, Exceptional, (133)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Terrace/patio

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

10.0 out of 10, Exceptional, (133)
"Our stay was great. Everything was as advertised and expected. "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Charming cottage in quiet area, close to beach & bay.
Guests can enjoy a porch with a sliding glass door leading to a cozy room.

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

9.8 out of 10, Exceptional, (278)
"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.
The "Grouper"
Stylish single-story home with a vibrant exterior, featuring a turquoise front door and a small garden area.

The "Grouper"

9.6 out of 10, Exceptional, (30)
"My stay was absolutely wonderful! The location is great, very convenient. The place itself is extremely comfortable, cozy, and it had everything we needed. The hosts were kind and attentive. It was truly worth every minute."
The price is €187
includes taxes & fees
31 Jul - 1 Aug
The "Grouper"
Charming, fully remodeled cottage steps from beach with WiFi & central AC
Charming single-story home with a flat roof and small porch area, featuring a simple design and a gravel driveway.

Charming, fully remodeled cottage steps from beach with WiFi & central AC

8.2 out of 10, Very good, (22)
"Very clean, comfortable, easy to reach the beach, and located in good neighbor "
Charming, fully remodeled cottage steps from beach with WiFi & central AC
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

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 €463
includes taxes & fees
24 Aug - 25 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Relax on the patio with a comfortable bench and wicker sofa, surrounded by a peaceful atmosphere.

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
Country Cottage Home
Relax in a serene outdoor space surrounded by a tropical mural and lush greenery.

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Loved our stay at the property. Would book it again!"
Country Cottage Home
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Enjoy a serene beachfront retreat surrounded by lush greenery and a tranquil ocean view.

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

9.8 out of 10, Exceptional, (89)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Across The Street From #1 Beach
Residential property with a two-story building, driveway, patio, and pool area surrounded by palm trees and greenery.

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Situated on a sandy beach, this property offers a beachfront location with lush greenery and a seating area.

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

9.6 out of 10, Exceptional, (21)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Residential area with modern homes and apartment buildings surrounded by lush greenery and palm trees.

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

8.8 out of 10, Excellent, (8)
"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
Quiet Nights of Quiet Stars on Anna Maria Island
Stunning single-story building with a front entrance and beautifully maintained garden.

Quiet Nights of Quiet Stars on Anna Maria Island

10.0 out of 10, Exceptional, (67)
"We found it just as described, nice quiet location, short walk to beach, lots of extras provided, Joel checked in with us a few times which we appreciated, we have rented at different places but never had the service Joel gives, he is really concerned you enjoy your stay and needs are met which they certainly were. Would definitely recommend this cute place to stay."
Quiet Nights of Quiet Stars on Anna Maria Island
Charming Ground Level Resort Style 3 unit Condo - unit C
Set amidst lush vegetation, this charming building offers a serene entrance with a decorative gate.

Charming Ground Level Resort Style 3 unit Condo - unit C

9.6 out of 10, Exceptional, (14)
"we will be back!"
Charming Ground Level Resort Style 3 unit Condo - unit C
1 Bedroom Duplex On Intracoastal W/ Beach Access
Enjoy a serene view of the water from this gazebo, which offers seating for relaxation.

1 Bedroom Duplex On Intracoastal W/ Beach Access

10.0 out of 10, Exceptional, (150)
"I would highly recommend staying here."
1 Bedroom Duplex On Intracoastal W/ Beach Access
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
Set amidst a serene natural environment, this single-story home offers an entrance and a garage.

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

9.8 out of 10, Exceptional, (20)
"Nice place "
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Relax on the waterfront deck with lounge chairs and a small table, taking in the view.

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is €279
includes taxes & fees
27 Jul - 28 Jul
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Enjoy ocean views from the comfort of your balcony.

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.4 out of 10, Exceptional, (6)
"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
Anna Maria Cottage with Golf Cart
Stylish home with a black door, flanked by windows, and a cozy porch area.

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
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Room was spacious. AC worked great. "
Elsa 1-night trip
Posted 10 hours ago
Kompose Boutique Hotel