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Check prices for these dates

Our top choices for Legacy Trail guest houses

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, (143 reviews)
"The hosts and the property were a joy to be involved with. We really enjoyed our stay."
United States
Dennis B.
The price is AU$356
includes taxes & fees
10 Nov - 11 Nov
Close to Siesta Key beach with a hot tub and a large garden

2. Coolest Downtown Neighborhood - Ebikes

Coolest Downtown Neighborhood - Ebikes
Central Sarasota
9.8 out of 10, Exceptional, (140 reviews)
"Cute place in a great location! Accurate listing, clean, and easy place to relax."
United States
Kathleen R.
The price is AU$273
includes taxes & fees
10 Nov - 11 Nov
Coolest Downtown Neighborhood - Ebikes

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

Siesta key Guest House 5 star on the water Private
South Sarasota
8.8 out of 10, Excellent, (21 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
United States
Scott E.
The price is AU$406
includes taxes & fees
10 Nov - 11 Nov
Siesta key Guest House 5 star on the water Private

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 AU$296
includes taxes & fees
10 Nov - 11 Nov
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
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.

Learn more about Legacy Trail

Venture to Siesta Key Beach and Lido Beach—just two of the top sights around Legacy Trail, a city also notable for its beaches and wildlife.

A paved road flanked by dense tropical vegetation.

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