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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Legacy Trail cottages

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
Englewood Central
9.8 out of 10, Exceptional, (8 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 AED 258
AED 863 total
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Exterior

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, (24 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
The price is AED 184
AED 530 total
includes taxes & fees
6 Jun - 7 Jun
Charming cottage for 2 across warm mineral springs park
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
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 AED 661
AED 1,340 total
includes taxes & fees
1 Jun - 2 Jun
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
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
Manasota Key
9.4 out of 10, Exceptional, (3 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 AED 661
AED 1,754 total
includes taxes & fees
2 Jun - 3 Jun
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is AED 382
AED 1,523 total
includes taxes & fees
21 Jun - 22 Jun
Lido Key Getaway - Bikes & Beach Gear
Interior

3 Mi to Beach! Englewood Family Gem + Private Pool

3 Mi to Beach! Englewood Family Gem + Private Pool
3.0 star property
Englewood
The price is AED 716
AED 1,901 total
includes taxes & fees
11 Jun - 12 Jun
3 Mi to Beach! Englewood Family Gem + Private Pool
Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 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 Inn On Siesta Key
Property grounds

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 AED 367
AED 915 total
includes taxes & fees
8 Jun - 9 Jun
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
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
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 AED 661
AED 1,743 total
includes taxes & fees
15 Jun - 16 Jun
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (67 reviews)
"Perfect location to Anna Maria Island-real “old Florida” feel."
United States
Mary W.
The price is AED 364
AED 775 total
includes taxes & fees
26 Jun - 27 Jun
The "Grouper"
Property grounds

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)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
The price is AED 349
AED 1,032 total
includes taxes & fees
14 Jun - 15 Jun
Coastal Luxury 7mi to Anna Maria Private Cottage
Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · 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 AED 602
AED 1,341 total
includes taxes & fees
15 Jun - 16 Jun
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Terrace/patio

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (123 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is AED 727
AED 1,655 total
includes taxes & fees
1 Jun - 2 Jun
Casey Key Beachfront Escape: Charming 1BR Cottage
Exterior

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

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, (5 reviews)
"Lowkey, quiet, clean, amenities to cook, great host and great view. Happy to go back again."
United States
Bryan S.
The price is AED 422
AED 717 total
includes taxes & fees
28 Jun - 29 Jun
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
1 bedroom, iron/ironing board, free WiFi, bed sheets

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (39 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is AED 551
AED 926 total
includes taxes & fees
2 Jun - 3 Jun
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Exterior

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.
The price is AED 1,037
AED 2,885 total
includes taxes & fees
2 Jun - 3 Jun
Yellow Palm Cottage steps from the beach
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
Pink Mango Cottage steps from the beach
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is AED 672
AED 1,978 total
includes taxes & fees
1 Jun - 2 Jun
Unwind Poolside + Walk to Beach! Sarasota Retreat
Property grounds

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 reviews)
"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.
Nest Cottage Across street from beach and Heated 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

Azul Resort Siesta Key

Azul Resort Siesta Key

10/10 Excellent
"After a terrible experience at another property, we moved our stay to Azul and had a fantastic experience. It’s very family friendly and we had our two children with us. The room was so clean and updated. The pool was nice and warm and it was very close to the beach. We had an issue with the A/C after hours and they had Maintenance there within 30 minutes. We will be staying here again, and would recommend staying here."
Nicole 2-night trip
Posted less than an hour ago
Azul Resort Siesta Key