A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sept - 6 Sept
In two months
2 Oct - 4 Oct

Our top choices for Legacy Trail guest houses

Beach nearby, sun-loungers, beach towels

1. Close to Siesta Key beach with a hot tub and a large garden

Close to Siesta Key beach with a hot tub and a large garden
Sarasota
9.8 out of 10, Exceptional, (137 reviews)
"We loved our stay here!! The place was clean and comfortable. Definitely coming back! "
United States
Cresta Blanca
The price is £190
includes taxes & fees
7 Aug - 8 Aug
Close to Siesta Key beach with a hot tub and a large garden
Beach

2. Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Central Sarasota
9.8 out of 10, Exceptional, (136 reviews)
"Stephanie is a great host. The coach house is very clean and comfortable and all of the extras available to us made the trip so good - like beach chairs, umbrellas, e-bikes. It’s a great location with Main Street walkable and fantastic beaches by car."
United Kingdom
Liz
The price is £141
includes taxes & fees
10 Aug - 11 Aug
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Terrace/patio

3. Siesta key Guest House 5 star on the water Private

Siesta key Guest House 5 star on the water Private
South Sarasota
8.6 out of 10, Excellent, (20 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
United States
Scott E.
The price is £270
includes taxes & fees
11 Aug - 12 Aug
Siesta key Guest House 5 star on the water Private
Marina

4. ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Whitfield Estates
7.4 out of 10, Good, (6 reviews)
"Looking for a couple nights close to Anna Maria Island without being ON the island. Turns out we were here once before and didnt realize it was the same place. Love the "Back Yard" surprises"
United States
Susan B.
The price is £159
includes taxes & fees
14 Aug - 15 Aug
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Beach

5. Cozy studio "glamping" shack 2 miles from Englewood Beach!

Cozy studio "glamping" shack 2 miles from Englewood Beach!
Englewood Central
8.8 out of 10, Excellent, (6 reviews)
"Wonderful place hosted by a very nice family"
United States
Stephen T.
The price is £144
includes taxes & fees
16 Aug - 17 Aug
Cozy studio "glamping" shack 2 miles from Englewood Beach!
Beach

6. Magical Guesthouse 1 mi from SRQ airport

Magical Guesthouse 1 mi from SRQ airport
Whitfield Estates
10.0 out of 10, Exceptional, (3 reviews)
"This house was absolutely charming! I caught myself In complete awe of every detail - from the fun decor, to the thoughtful inclusion of all kitchen supplies to make a full meal, to the soft shower towels and the incredibly comfortable bed, bedding and pillows! Fantastic stay."
United States
Alyssa D.
The price is £182
includes taxes & fees
28 Aug - 29 Aug
Magical Guesthouse 1 mi from SRQ airport
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 Guest Houses information

Number of reviews
25,042
Accommodation
0 Guest Houses
Lowest Price
£53
Highest Price
£173

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