Available 7/1/2026
Vacation rental or Long terms flexible lease options. Fully furnished. 5 min bike ride from the #1 beach in the country
New Kitchen, New Bathrooms. One of a kind cottage. Pond with fountain in the backyard, New Kitchen, new bathrooms. Can be unfurnished for long term tenancy. Brand New Ice cold A/C. 2 solar Tubes. Big Lanai
Walk to the beach. Sweetheart house on Twin Oak Pond. Sit in front of your fireplace, watch and listen to the fountain in the pond outside your window. Ground level 2 bedrooms and 2 full baths, large screened porch, tile floors, open kitchen and wood burning fireplace. Pet friendly. Deal with the owner directly. Not a management company.
$4200 30 day min
$3500. 12 month lease
Shorter than 30 day is available at a higher rate.
Tenant is responsible for
Power bill Water / sewer / trash
Internet when renting long term.
Pet Fee if applicable
5255 Winding Way
Sarasota, FL 34242
Apartment building
Studio-2 beds
Available units
This building may have units for rent or for sale. Select a unit to contact.
What's special
New kitchenLarge screened porchBig lanaiTile floorsFully furnishedNew bathroomsWood burning fireplace
Facts, features & policies
Unit features
Appliances
- Dishwasher
- Freezer
- Oven
- Refrigerator
Flooring
- Tile
Heating
- Heat pump
Neighborhood: 34242
Areas of interest
Use our interactive map to explore the neighborhood and see how it matches your interests.
Travel times
Walk, Transit & Bike Scores
Nearby schools in Sarasota
GreatSchools rating
- 9/10Phillippi Shores Elementary SchoolGrades: PK-5Distance: 1.5 mi
- 6/10Brookside Middle SchoolGrades: 6-8Distance: 2.3 mi
- 5/10Sarasota High SchoolGrades: 9-12Distance: 3.7 mi
Frequently asked questions
What schools are assigned to 5255 Winding Way?
The schools assigned to 5255 Winding Way include Phillippi Shores Elementary School, Brookside Middle School, and Sarasota High School.
What neighborhood is 5255 Winding Way in?
5255 Winding Way is in the 34242 neighborhood in Sarasota, FL.
