Search Legacy Trail Cottage Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Legacy Trail cottages

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, (23 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is ¥8,647
¥23,575 total
includes taxes & fees
May 14 - May 15
Charming cottage for 2 across warm mineral springs park

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 reviews)
"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 ¥12,735
¥41,376 total
includes taxes & fees
May 8 - May 9
Coastal Luxury 7mi to Anna Maria Private Cottage

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is ¥47,085
¥61,938 total
includes taxes & fees
May 11 - May 12
The Inn On Siesta Key

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (65 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
The price is ¥15,565
¥33,798 total
includes taxes & fees
May 25 - May 26
The "Grouper"

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, (6 reviews)
"We all had a wonderful stay!!! The home was clean, beautifully furnished and appointed with all sorts of amenities: coffee, tea, beach chairs, towels, laundry detergent and more. The fenced in yard was wonderful for privacy and the dogs. The owners were very responsive to our questions and needs. We would definitely stay here again!!! Not only was the home super cute, it was close to everything: grocery store, pharmacy, downtown, beaches and restaurants. "
United States
Jade C.
The price is ¥12,066
¥38,965 total
includes taxes & fees
May 18 - May 19
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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 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 ¥39,305
¥88,358 total
includes taxes & fees
May 11 - May 12
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (121 reviews)
"It was a cool place. Best experience on the beach I have had in my life. The one thing is that they could use a few updates, you can tell it’s been some years since they took the photos till now. However, it was a great time for the family. You won’t regret it."
United States
James
The price is ¥39,115
¥80,917 total
includes taxes & fees
May 10 - May 11
Casey Key Beachfront Escape: Charming 1BR Cottage

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
cortez
10.0 out of 10, Exceptional, (104 reviews)
"The host was always available! The cottage is adorable and homey. Wonderful location and had everything you need for a fun experience."
United States
Janice C.
The price is ¥25,835
¥45,806 total
includes taxes & fees
May 18 - May 19
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

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, (6 reviews)
"Kristin made it easy to check in and out a very pleasant stay thank you"
United States
Deb H.
The price is ¥28,300
¥57,339 total
includes taxes & fees
May 7 - May 8
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is ¥11,005
¥58,226 total
includes taxes & fees
May 8 - May 9
Lido Key Getaway - Bikes & Beach Gear

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Palmetto
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
The price is ¥14,464
¥38,041 total
includes taxes & fees
May 19 - May 20
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Outdoor Kitchen & Gaming Garage: Bradenton Retreat

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Bradenton
Outdoor Kitchen & Gaming Garage: Bradenton Retreat

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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ¥15,565
¥47,334 total
includes taxes & fees
May 21 - May 22
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is ¥41,349
¥76,219 total
includes taxes & fees
May 10 - May 11
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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, (6 reviews)
"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 ¥32,333
¥79,744 total
includes taxes & fees
May 18 - May 19
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (4 reviews)
"The property was very well stocked, had a bowl for our dog an very clean! It was the petfect place for our visit with local family. The "Florida Room" was lovely and the view was excellent. Very peaceful location."
United States
Marie W.
The price is ¥19,653
¥32,616 total
includes taxes & fees
May 26 - May 27
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
Romantic Island Getaway! Just Steps from the Beach

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)
"Everything was fantastic!"
United States
Kevin O.
The price is ¥35,487
¥127,599 total
includes taxes & fees
May 18 - May 19
Beautiful Guest House Near the Beach with Private Pool!

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, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is ¥47,009
¥101,693 total
includes taxes & fees
May 12 - May 13
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Legacy Trail Cottages information

Number of reviews
954
Accommodation
51 Cottages
Lowest Price
¥23,575
Highest Price
¥127,599

Explore a world of travel with Expedia