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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Featured Cottages in Legacy Trail

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

2.0 star property
Englewood Central
The price is NZ$596
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio
The Inn On Siesta Key

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (188)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is NZ$527
includes taxes & fees
11 Nov - 12 Nov
The Inn On Siesta Key
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, (10)
"I'm currently working in the area and this place made it even easier being away from home I've enjoyed the area and the place "
United States
Andy B.
The price is NZ$276
includes taxes & fees
9 Nov - 10 Nov
Charming cottage for 2 across warm mineral springs park
Beach nearby
Island Life! King Bed Studio-Steps to beach

Island Life! King Bed Studio-Steps to beach

Manasota Key
9.6 out of 10, Exceptional, (168)
"My husband and I stayed at the Bay Breeze Bungalow for 4 days and cannot wait to come back. Perfect location, 2 minute walk to the beach. Quiet neighborhood. We were right next to the pool, and even with kids swimming, it was quiet. We had a question regarding parking, (our confusion) we received a call back within a 1/2 hour. The Bungalow was very clean and had the essentials we needed. Being May, it was extremely warm, the air conditioner always kept the place cool. I cannot say enough...
United States
Karen L.
The price is NZ$376
includes taxes & fees
30 Nov - 1 Dec
Island Life! King Bed Studio-Steps to beach
Exterior
#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, (8)
"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.
The price is NZ$276
includes taxes & fees
10 Nov - 11 Nov
#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

Bradenton
10.0 out of 10, Exceptional, (2)
"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 NZ$488
includes taxes & fees
11 Nov - 12 Nov
7mi to Anna Maria Newly Renovated Private Cottage
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
The price is NZ$432
includes taxes & fees
9 Nov - 10 Nov
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Outdoor dining
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, (104)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
The price is NZ$803
includes taxes & fees
9 Nov - 10 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Exterior
The "Grouper"

The "Grouper"

Sunny Shores
9.2 out of 10, Wonderful, (40)
"Very clean and nice place ."
United States
Sherry S.
The price is NZ$379
includes taxes & fees
12 Nov - 13 Nov
The "Grouper"
Outdoor dining
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.
The price is NZ$542
includes taxes & fees
10 Nov - 11 Nov
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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

2.0 star property
Nokomis
The price is NZ$303
includes taxes & fees
1 Dec - 2 Dec
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
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, (176)
"clean, nice amenities and great location"
United States
Robert K.
The price is NZ$708
includes taxes & fees
11 Nov - 12 Nov
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior
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
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
Terrace/patio
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.
The price is NZ$692
includes taxes & fees
21 Nov - 22 Nov
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

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.
The price is NZ$901
includes taxes & fees
15 Nov - 16 Nov
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
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
8.0 out of 10, Very good, (1)
"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 NZ$1,000
includes taxes & fees
9 Nov - 10 Nov
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Terrace/patio
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.
The price is NZ$1,129
includes taxes & fees
11 Nov - 12 Nov
Nook Cottage Across street from beach and Heated Pool
Terrace/patio
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)
"The location was perfect with close beach access and surrounded by a lot of fun businesses. We loved being over the pizza shop, could go down there and grab food or drinks! We enjoyed our stay very much!"
United States
Sarah E.
Adorable Cottage with Covered Balconies and Private Pool
Exterior
Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach

2.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (3)
"Although there are laundry facilities on property, the area is kept locked and this unit is not permitted access. We were unable to do any laundry unless we traveled two miles to Holmes Beach to the Laundromat. This property IS very quiet. The trolley stops are literally at the end of the driveway, but there are no shops or businesses within close walking distance. Also, there were beach chairs and towels, but THERE ARE NO EXTRAS here, which is unlike any other Vrbo/AirBnb we have visited. There...
United States
Amy
Romantic Island Getaway! Just Steps from the Beach
Terrace/patio
5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!

South Sarasota
The price is NZ$903
includes taxes & fees
21 Nov - 22 Nov
5 star Guest House heated pool on the water!
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
"Clean room and hitel"
Korey 2-night trip
Posted 3 days ago
DoubleTree by Hilton Sarasota Bradenton Airport

Find out more about Legacy Trail

Legacy Trail Cottages information

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