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Our top choices for Legacy Trail cottages

House (2 Bedrooms) | Interior
Relax in Hot Tub, Walk to Springs: North Port Home

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
Relax in Hot Tub, Walk to Springs: North Port Home
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio
The Inn On Siesta Key

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
$314 nightly
The price is $355
Dec 23 - Dec 24
Total with taxes and fees
The Inn On Siesta Key
Exterior
Charming cottage for 2 across warm mineral springs park

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.
$155 nightly
The price is $173
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
Exterior
#3 Small house walking distance to Warm Mineral Spring

#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.
$140 nightly
The price is $156
Dec 22 - Dec 23
Total with taxes and fees
#3 Small house walking distance to Warm Mineral Spring
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

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.
$285 nightly
The price is $318
Jan 1 - Jan 2, 2026
Total with taxes and fees
7mi to Anna Maria Newly Renovated Private Cottage
Outdoor dining
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

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
2.0 star property
Englewood Central
$226 nightly
The price is $252
Jan 6 - Jan 7, 2026
Total with taxes and fees
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Exterior
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

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Manasota Key
9.0 out of 10, Wonderful, (2)
"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.
$387 nightly
The price is $428
Dec 24 - Dec 25
Total with taxes and fees
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Exterior
The "Grouper"

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.
$189 nightly
The price is $211
Dec 22 - Dec 23
Total with taxes and fees
The "Grouper"
Terrace/patio
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

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

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Casey Key
9.4 out of 10, Exceptional, (108)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
$404 nightly
The price is $451
Dec 24 - Dec 25
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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.
$326 nightly
The price is $326
Jan 4 - Jan 5, 2026
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

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
$300 nightly
The price is $334
Jan 6 - Jan 7, 2026
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
Exterior
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

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.
$350 nightly
The price is $390
Dec 22 - Dec 23
Total with taxes and fees
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
Exterior
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

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.
$403 nightly
The price is $446
Dec 22 - Dec 23
Total with taxes and fees
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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.
$437 nightly
The price is $488
Jan 19 - Jan 20, 2026
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Terrace/patio
5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!
South Sarasota
$444 nightly
The price is $496
Dec 22 - Dec 23
Total with taxes and fees
5 star Guest House heated pool on the water!
Terrace/patio
Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
$640 nightly
The price is $700
Dec 22 - Dec 23
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool
Terrace/patio
Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
$997 nightly
The price is $1,079
Dec 22 - Dec 23
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool
Exterior
Adorable Cottage with Covered Balconies and Private Pool

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.
$851 nightly
The price is $950
Jan 3 - Jan 4, 2026
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
Terrace/patio
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

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.
$370 nightly
The price is $413
Dec 22 - Dec 23
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Exterior
Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.6 out of 10, Excellent, (30)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
$794 nightly
The price is $885
Jan 15 - Jan 16, 2026
Total with taxes and fees
Beautiful Guest House Near the Beach with 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

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Was so close to airport and on site restaurant was very good."
WANDA 1-night trip
Posted 1 day ago
DoubleTree by Hilton Sarasota Bradenton Airport

Find out more about Legacy Trail

Legacy Trail Cottages information

Number of reviews
559
Accommodation
61 Cottages
Lowest Price
$156
Highest Price
$1,079

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