Available: Right Now
Listed: 20/04/2025
Osprey, FL
Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida.Enjoy exploring Historic Spanish Point, kayaki...
Available: Right Now
Listed: 21/04/2025
Osprey, FL
Relaxed yet Refined, this 2-bedroom condo embodies a laid back attitude and care free state of mind. Get sun-drenched by the pool, or enjoy a friendly tennis match on private courts. Entertaining is effortless in the fully upgraded spacious and open ...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Bay Street condominiums are a newer complex (2017) in a beautiful gated community right off of Tamiami trail and a quick 10 minute drive from Nokomis beach or 15 minutes from white sandy beaches world renowned Siesta Key beaches. Screened lanai o...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Decisions, decisions...which beach to go to today? Siesta Key, Nokomis, Venice, Lido, Englewood.... Or bike ride on the Legacy Trail to the beach, perhaps kayak on Little Sarasota Bay (water sport rentals avail nearby). Did someone say Siesrs Key Rum...
Available: Right Now
Listed: 21/04/2025
Osprey, FL
Intercoastal, Blackburn Bay waterfront home with boating facilities near Casey Key and Siesta Key. On a point facing the setting sun. This is simply paradise.The pier is long, and the water deep enough to handle most boat docking needs. The large...
Available: Right Now
Listed: 23/04/2025
South Tamiami Trail, Osprey, Sarasota County, FL 34229, USA
This amazing new listing offers 2 bedrooms and 2 bathrooms, perfect for a relaxing getaway with family or friends. Inside, you'll find a spacious and well-appointed living area with comfortable furnishings and all the amenities you need to make your ...
Available: Right Now
Listed: 24/04/2025
Osprey, FL, US
Welcome to your dream home in Sarasota! Fully renovated PadSplit with high-quality finishes Stone countertops, luxury vinyl plank flooring, and plantation shutters for privacy Well-equipped kitchen with top-of-the-line appliances Conveniently located...
Available: Right Now
Listed: 20/04/2025
Osprey, FL
Bay Acres Bungalow - AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Iconic local attractions like Casey Key Beach, Oscar Shearer State Park, and Histori...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Great location at Osprey Harbor Villas located at the swing bridge going onto Casey Key. Located between Siesta Key and Venice and is a great area for walking, biking, boating and kayaking. Gated, secure and quiet complex with 2 under building parkin...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Relax in private secluded luxury. Lush, ornamental plantings surround the beautiful backyard and pool deck. Spacious and private, the backyard features a covered lanai, open pool and spa and outdoor shower. Patio deck includes outdoor grill area....
Available: 10/05/2025
Listed: 26/04/2025
1859 Highland Rd, Unit 1859
You will love the location!! Just steps from the community pool. Spacious 2-bedroom / 2 Bathroom Villa in a wonderful neighborhood with ample parking space. You can walk to the charming Shoreland Park, or right across the street is Oscar Scherer Stat...
Available: 15/05/2025
Listed: 26/04/2025
12413 Osorio Ct Sarasota Fl 34238, Unit 103
Minimum 1 Month of rental. Rental prices excluding seasonal term Dec2025 -Apr 2026January - March2026,Rate is$ 6,000per monthApril, December$ 3,000per monthMay-November$ 2,600per monthComplex " Esplanade on Palmer ranch ...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Unwind with your entire family at this serene retreat. Nestled discreetly just off Tamiami, it offers a heated pool and spa, an outdoor kitchen, and TVs in every room and the living room. Explore the Legacy Trail with complimentary bikes or enjoy a k...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
2bd/2ba condo nestled in a quiet community. This upstairs unit offers large 16ft ceilings, fully furnished open and airy space with large LR, open kitchen, breakfast bar, large screen TV, Wifi, Desk and WFH area. Private deck. Great walk-ability and ...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Location, location, location for Outdoor Lovers! . This newly renovated and furnished house is just steps from boat ramp and fishing pier. Launch your kayaks and watch stunning sunsets over Casey Key and Gulf of Mexico. This fabulous house inc...
Available: Right Now
Listed: 20/04/2025
Osprey, FL
Look no further than this private guesthouse that is a great retreat for the family. Enjoy the pool, hot tub on a nice warm day. Go swing the tennis racket on the private courts. Or take a quick drive to Nokomis Beach to lay out, catch some rays, or ...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Summary:This amazing new listing offers 2 bedrooms and 2 bathrooms, perfect for a relaxing getaway with family or friends. Inside, you'll find a spacious and well-appointed living area with comfortable furnishings and all the amenities you need t...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Enjoy the spectacular sunsets from our pier overlooking Sarasota Bay, We are located very close to all the amenities and beaches !!! Play in the morning and lounge by the pool in the afternoon !!! Soaking up the sunshine and enjoying all that the Gul...
Available: Right Now
Listed: 20/04/2025
Osprey, FL
This meticulously designed 3-bedroom, 2 bath home presents a blend of modern elegance and coastal charm, providing the ideal retreat.The home features a large stone fireplace and wood beams in the family room which is open to the kitchen. The kit...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
2 bedroom condo and have a lovely water view to look forward to. The condo has a den with a queen size sofa bed. The condo also has two televisions. The bathroom is big with a suite in it. Entire floor has tiles in bathrooms and laundry room. The res...
Available: Right Now
Listed: 25/04/2025
Osprey, FL
Summary:Step into a sunlit, single-story retreat with two inviting bedrooms and two modern bathrooms. Designed for families or groups of friends, our home seamlessly blends comfort with elegance. Located just moments away, dive into the vibrant S...
Available: Right Now
Listed: 23/04/2025
Osprey, FL
Enjoy memorable sunsets, with a private view and revel in all the local charm and activities the Casey Key area have to offer. Our villa has the perfect balance of ambiance and enjoyment you are looking for in your vacation to the Sarasota/Venice are...
Osprey, FL has a population of 6,734, while the median age is 58. The household income in Osprey, FL is around $77,225. The homeownership rate among the residents is 85%. The median residential property value in Osprey, FL that you should keep in mind is $386,300.
🏠 Total listings for rent | 48 properties |
💵 Min. monthly rent | from $1,101/mo |
🐾 Pet-friendly properties | 23 rentals |
🛋 Furnished rentals | 2 listings |
💧 With utilities included | 1 rental |
🚗 With parking/garage | 34 properties |
You can find a variety of rental options in Osprey, FL including condos, houses, and apartments.
Rental properties in Osprey, FL often come with sought-after amenities such as air conditioning, parking, dishwasher, pool, and balcony options.
Osprey, FL offers a somewhat walkable environment with sidewalks and pedestrian-friendly areas. However, it is advisable to check specific neighborhoods and their respective walkability scores to determine the level of walkability that fits your preferences.
Osprey, FL is home to several schools and educational institutions. Some notable options include Pine View School, a renowned public school for gifted students, and the State College of Florida, Manatee-Sarasota, which offers a range of undergraduate programs.