Downtown Osprey, Florida






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Discounts For Customers

Support Local Businesses

Fight Cancer


ShopDowntown.org and the American Cancer Society (ACS) have launched a new program that provides discounts at local stores while raising money to fund cancer research, programs and services. Shoppers who donate $20 or more to the American Cancer Society are eligible to receive a free Shop Downtown Discount Card. Simply make a donation online, get your receipt verified, and receive your digital discount card to save up to 15% off at participating businesses.

When you get a Shop Downtown Discount Card, you help support your neighbors, the local economy, and the American Cancer Society’s mission to save lives, celebrate lives and lead the fight for a world without cancer. You also can get great savings on a variety of products and services every time you patronize a participating business. It’s a win/win situation.













The American Cancer Society does not endorse any product or service.




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Things to do in Osprey, Florida

Main Street of old Downtown Osprey speaks to once what was and what could be once again. As Osprey the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.

Downtown Osprey brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Downtown Osprey hosts several events per year for your listening enjoyment but visit your piano shop to learn how to play and possibly purchase your grand, upright or digital piano. Don't forget the specialty work involved such as tuning and moving which are performed by skilled technicians.

Downtown Osprey gives several options to find the right piece of art as it takes time and a diligent effort to get just the right piece. Shopping for art downtown is the best way to locate your next purchase.

Downtown Osprey brings a custom fit every time a shoe is bought locally. Nothing beats the hands on experience of shoe shopping to add to your collection of Men's, Women's and Children's shoes. Try them on, walk around and make sure you have the best fit as every manufacturer is a bit different on sizing.

Why do you love downtown?

Heather Anne Hopfinger
You do not have to walk far for a movie or some place great to shop or workout

Jeremy Holmes
Supporting small business downtown is a very real way to support your local community. Downtown businesses are locals, like us.

Kristin Miller
Things you can't find anywhere else

Robert Drennan
Planning a trip and want to visit after reading all the reviews

Christy Richards
Because I love to shop local and the stores and owners make your visit welcoming inviting you to return again with a smile on their face.

Restaurants in Osprey, Florida


Downtown Osprey Hotels

Finding the best hotel in Downtown Osprey can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:

Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.

Bring an actual credit card to avoid deposits and pre-authorizations consuming money in your checking account which will reduce your available balance. Hotels that accept paper cash often ask for a hefty deposit to cover potential damages in your room leaving you scrambling to find an ATM.

Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.


Bentley's Boutique Hotel
 1660 South Tamiami Trail


Virage Hotel
 1650 South Tamiami Trail