A wooden pathway surrounded by dense greenery and trees.

Search Legacy Trail Cottage Rentals from CA $197

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Our top choices for Legacy Trail cottages

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The price is CA $481
CA $622 total
includes taxes & fees
Jul 10 - Jul 11
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, (25 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
The price is CA $64
CA $197 total
includes taxes & fees
Jul 8 - Jul 9
Charming cottage for 2 across warm mineral springs park

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is CA $266
CA $693 total
includes taxes & fees
Jul 8 - Jul 9
Home < 1-mi Walk to Warm Mineral Springs Park!

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
9.8 out of 10, Exceptional, (8 reviews)
"Kristin made it easy to check in and out a very pleasant stay thank you"
United States
Deb H.
The price is CA $256
CA $571 total
includes taxes & fees
Jul 9 - Jul 10
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee

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
9.6 out of 10, Exceptional, (4 reviews)
"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 CA $206
CA $618 total
includes taxes & fees
Jul 18 - Jul 19
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly

NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly
Myakka City
10.0 out of 10, Exceptional, (23 reviews)
"Location was optimum for us. "
United States
James K.
The price is CA $250
CA $560 total
includes taxes & fees
Jul 20 - Jul 21
NEW-Lakefront /on 5 acres /near Lakewood Ranch / Pool / Pet Friendly

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (72 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $141
CA $301 total
includes taxes & fees
Jul 15 - Jul 16
The "Grouper"

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (78 reviews)
"It was perfect. We had a great time."
United States
Karen M.
The price is CA $352
CA $767 total
includes taxes & fees
Jul 12 - Jul 13
Direct Beachfront 2BR Cottage on Casey Key!

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
Englewood Central
9.8 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay at this property. Home is perfect for couples or a small family. Very clean and adorable set up. Love the back yard and lanai! Thanks for a great stay - we would stay again."
United States
Mandy A.
The price is CA $100
CA $341 total
includes taxes & fees
Jul 8 - Jul 9
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $820
CA $1,301 total
includes taxes & fees
Jul 12 - Jul 13
Siesta Heron 6 / Sunset

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
Yellow Palm Cottage steps from the beach

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
Pink Mango Cottage steps from the beach

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is CA $249
CA $477 total
includes taxes & fees
Jul 8 - Jul 9
Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (10 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
The price is CA $96
CA $349 total
includes taxes & fees
Jul 9 - Jul 10
Coastal Luxury 7mi to Anna Maria Private Cottage

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (126 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is CA $462
CA $976 total
includes taxes & fees
Jul 8 - Jul 9
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is CA $178
CA $495 total
includes taxes & fees
Jul 8 - Jul 9
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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 reviews)
"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.
Cabana Cottage Across street from Beach and Heated Pool

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (89 reviews)
"Great location and very clean. The host was responsive and easy to communicate with throughout our stay. The property had everything we needed and more, and all amenities were well-maintained. Would definitely stay here again."
United States
Jaiden W.
The price is CA $141
CA $432 total
includes taxes & fees
Aug 2 - Aug 3
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
Beautiful Guest House Near the Beach with Private Pool!

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Englewood
9.8 out of 10, Exceptional, (42 reviews)
"Wow....this is one of the best VRBOs we've stayed in. Evan was a great host, very welcoming, helpful and quick to respond to questions. Location is so convenient to either Lemon Bay or the beach."
United States
Marla W.
The price is CA $781
CA $1,415 total
includes taxes & fees
Jul 31 - Aug 1
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
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
662
Accommodation
54 Cottages
Lowest Price
CA $197
Highest Price
CA $1,415

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