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Our top choices for Legacy Trail cottages

Relax in Hot Tub, Walk to Springs: North Port Home

Relax in Hot Tub, Walk to Springs: North Port Home
3.0 star property
North Port
The price is €191
includes taxes & fees
16 Dec - 17 Dec
Relax in Hot Tub, Walk to Springs: North Port Home

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is €518
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is €141
includes taxes & fees
1 Jan - 2 Jan 2026
Charming cottage for 2 across warm mineral springs park

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (3)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is €238
includes taxes & fees
16 Dec - 17 Dec
7mi to Anna Maria Newly Renovated Private Cottage

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
9.0 out of 10, Wonderful, (9)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is €136
includes taxes & fees
16 Dec - 17 Dec
#3 Small house walking distance to Warm Mineral Spring

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
2.0 star property
Englewood Central
The price is €245
includes taxes & fees
27 Dec - 28 Dec
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Casey Key
9.2 out of 10, Wonderful, (69)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

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

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Manasota Key
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""
United States
Anabel P.
The price is €375
includes taxes & fees
24 Dec - 25 Dec
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (43)
"A beautiful little place to stay only minutes away from the beach! Very cozy and clean! "
United States
savana w.
The price is €184
includes taxes & fees
16 Dec - 17 Dec
The "Grouper"

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

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
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. "
United States
Rolly N.
The price is €261
includes taxes & fees
16 Dec - 17 Dec
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
2.0 star property
Sarasota
The price is €293
includes taxes & fees
6 Jan - 7 Jan 2026
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

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

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Manasota Key
10.0 out of 10, Exceptional, (1)
"This was a great stay. It was very clean and seemed like a brand new renovation. They provide plenty to do from two bicycles for cruising, a few kayaks and indoor games. The kitchen was stocked if you chose to stay in and cook. Lastly, the hosts were great to work with. We will stay again. "
United States
John C.
The price is €387
includes taxes & fees
16 Dec - 17 Dec
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee

New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
Myakka City
9.0 out of 10, Wonderful, (2)
"very clean and homey"
United States
michelle r.
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is €484
includes taxes & fees
18 Dec - 19 Dec
Pink Mango Cottage steps from the beach

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
The price is €490
includes taxes & fees
18 Dec - 19 Dec
Yellow Palm Cottage steps from the beach

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (177)
"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. "
United States
Kim C.
The price is €431
includes taxes & fees
2 Jan - 3 Jan 2026
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!
South Sarasota
The price is €431
includes taxes & fees
16 Dec - 17 Dec
5 star Guest House heated pool on the water!

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
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."
United States
Marti C.
The price is €436
includes taxes & fees
18 Dec - 19 Dec
Nest Cottage Across street from beach and Heated Pool

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (25)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is €377
includes taxes & fees
16 Dec - 17 Dec
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.6 out of 10, Exceptional, (41)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
United States
C. S.
The price is €381
includes taxes & fees
16 Dec - 17 Dec
Adorable Cottage with Covered Balconies and Private Pool
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

Find out more about Legacy Trail

Legacy Trail Cottages information

Number of reviews
446
Accommodation
61 Cottages
Lowest Price
€136
Highest Price
€518

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