A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Legacy Trail vacation rentals

An outdoor patio with a grill, white chairs, and a red umbrella.

1. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,484 reviews)
"This place was perfect!"
United States
Kat
The price is P8,628
P9,750 total
includes taxes & fees
Nov 25 - Nov 26
Hibiscus Suites - Gateway to Siesta Key
A pool area with a waterfall feature, lounge chairs, and palm trees.

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,057 reviews)
"Great resort and location!"
United States
Christine
The price is P9,501
P12,372 total
includes taxes & fees
Dec 3 - Dec 4
Tropical Beach Resorts
A pathway with wooden posts and ropes, leading to a building with a sign indicating a nautical room.

3. Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (320 reviews)
"Debbie and Sean are excellent hosts. Very clean, very comfortable, very quiet. Pet friendly, which is awesome also. Great location also just a couple miles from downtown or the beach.."
United States
Joseph
The price is P10,233
P11,564 total
includes taxes & fees
Nov 16 - Nov 17
Kon Tiki Inn
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

4. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (700 reviews)
"Enjoyed our stay"
United States
Robin
The price is P11,656
P13,172 total
includes taxes & fees
Dec 6 - Dec 7
A Beach Retreat
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

5. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (208 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is P14,106
P15,941 total
includes taxes & fees
Nov 24 - Nov 25
SeaSpray Resort
A beach with white sand, wooden beach chairs, and a clear blue sky.

6. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,334 reviews)
"Great location that's very close to the beach, large and clean room with a kitchenette, and very helpful and friendly staff. Loved our stay here!"
United States
Bob
The price is P10,537
P12,974 total
includes taxes & fees
Nov 15 - Nov 16
Captiva Beach Resort
A compact living space with a sofa, a television, a ceiling fan, and a door.

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (392 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is P3,860
P12,852 total
includes taxes & fees
Nov 22 - Nov 23
Tiny House Siesta
A beach with a clear sky and calm sea.

8. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (213 reviews)
"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...
United States
Karen Jean
The Inn On Siesta Key
A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

9. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (847 reviews)
"I loved this hotel"
United States
Raisare
The price is P18,192
P22,335 total
includes taxes & fees
Dec 13 - Dec 14
Bridgewalk Resort
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

10. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (488 reviews)
"Location was perfect"
United States
Amylynn
The price is P9,106
P11,525 total
includes taxes & fees
Dec 9 - Dec 10
Pelican Post at Anna Maria Island Inn
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

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