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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 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 867 total
includes taxes & fees
2 Jun - 3 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

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 624
AED 1,717 total
includes taxes & fees
2 Jun - 3 Jun
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
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 294
AED 828 total
includes taxes & fees
4 Jun - 5 Jun
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
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
6 Jun - 7 Jun
New-Lakewood Ranch Private Cottage/Pool on 5 Acres of Waterfront-Lake Manatee
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"
Interior

3 Mi to Beach! Englewood Family Gem + Private Pool

3 Mi to Beach! Englewood Family Gem + Private Pool
3.0 star property
Englewood
3 Mi to Beach! Englewood Family Gem + Private Pool
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
Marina

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
The price is AED 331
AED 1,547 total
includes taxes & fees
30 Jun - 1 Jul
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
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 1,344 total
includes taxes & fees
9 Jun - 10 Jun
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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 753
AED 1,879 total
includes taxes & fees
2 Jun - 3 Jun
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom 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.
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (73 reviews)
"It was perfect. We had a great time."
United States
Karen M.
The price is AED 727
AED 1,745 total
includes taxes & fees
2 Jun - 3 Jun
Direct Beachfront 2BR Cottage on Casey Key!
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
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
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
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 922 total
includes taxes & fees
2 Jun - 3 Jun
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
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
Unwind Poolside + Walk to Beach! Sarasota Retreat
Exterior

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, (183 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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
2 Jun - 3 Jun
Casey Key Beachfront Escape: Charming 1BR Cottage
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

6/10 Okay
"The property was okay, it’s an older remodel hotel. Breakfast was"
Alicia 1-night trip
Posted less than an hour ago
Spark by Hilton Sarasota Siesta Key Gateway