A nest on a wooden platform by a lake at sunset with birds flying around.

Vacation homes in Osprey

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Vacation homes in Osprey

A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

A beach scene with a hammock, palm trees, and the sun setting over the ocean.

A room with a large window overlooking a beach, a small table with a placemat, and a chair with a decorative backrest.

A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

1. A Beach Retreat

Casey Key

$205

$231 total

includes taxes & fees

Nov 4 - Nov 5

A wooden pathway leading to a beach with clear turquoise water and a wooden railing on one side.

A swimming pool with a glass enclosure, surrounded by patio furniture and plants.

A residential house with a tiled roof, surrounded by well-maintained lawns and various tropical plants.

A covered outdoor area with a concrete path, surrounded by various tropical plants and a palm tree.

2. Tropical Villas of Venice Beach

Venice Island

A wooden structure with a thatched roof overlooking a beach.

A kitchen with a built-in oven and a view of a lake with boats and a dock.

A beach with a sandy shore and gentle waves.

A bedroom with a wooden ceiling, a TV mounted on the wall, a bed with white bedding, and a view of a garden through an open door.

3. Casey Key Resort

Casey Key

$215

$264 total

includes taxes & fees

Oct 19 - Oct 20

An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

A covered outdoor deck with a table and chairs, overlooking a body of water and palm trees.

A marina with multiple boats docked, surrounded by residential buildings and palm trees.

A modern kitchen with white cabinetry, a built-in dishwasher, and a coffee maker.

4. Chadwick Cove Resort & Marina

Manasota Key

$161

$630 total

includes taxes & fees

Oct 19 - Oct 20

A building with a covered entrance, a small porch, and a door with a sign.

A modern living room with a TV, a lamp, and a pool view.

A courtyard with palm trees, outdoor seating, and a building with a balcony.

A living room with a dining table, chairs, sofas, a TV, and a ceiling fan.

5. Venice Beach Villas

Venice Island

A pathway with wooden posts and ropes, leading to a building with a sign indicating a nautical room.

A room with a grey sofa, a white table with chairs, a TV mounted on the wall, and a wooden ceiling.

A covered outdoor area with a wooden fence, palm trees, and a building with a blue wall and a yellow door.

A bedroom with a wooden bed, a dresser, a mirror, a starfish wall decoration, and a painting of a sailboat.

6. Kon Tiki Inn

Venice Island

A sunset view with a glass of red wine on a dock.

A sign welcoming visitors to Paradise Cove, indicating luxury vacation rentals.

A hammock tied to a wooden post with a view of a pier and water in the background.

7. Paradise Cove at Lemon Bay

Olde Englewood Village

A cozy living room with a white sofa, a blue bench, a white table, and a patterned rug.

A covered outdoor patio with a sofa, a table, and a chair.

A modern living room with a white sofa, a coffee table, and a TV on a stand. There is a door leading to another room and a mirror on the wall.

A bedroom with a large bed, a dresser, a mirror, and a painting on the wall.

8. Steps to Dtwn & Bay! Snowbird Escape in Englewood

Olde Englewood Village

A living room with a blue sofa, a wooden coffee table, wicker furniture, and a ceiling fan.

A modern kitchen with dark wooden cabinets, stainless steel appliances, and a marble backsplash.

A dining area with a wooden table and chairs, a black pendant light, and a kitchen area with a dark cabinet and a blue vase.

9. Englewood Bungalow 1 Mi to Beach: Pets Welcome!

South Venice

A dining area with a wooden table and white chairs, a potted plant, and a painting on the wall.

A hot tub under a covered patio with a view of a house and trees.

A house with a dark front door, a welcome bench, and a small garden with tropical plants.

A modern living room with a sofa, TV, and a dining area visible through an open door.

10. Relax in Hot Tub, Walk to Springs: North Port Home

North Port

An outdoor patio area with white tables and chairs, surrounded by potted plants and palm trees.

A bedroom with a bed, a ceiling fan, a TV mounted on the wall, a window with curtains, and a view of a building outside.

A modern living room with a grey sofa, a coffee table, and a ceiling fan.

A kitchen with white cabinets, a stainless steel sink, a microwave, and a woven basket with utensils.

11. Walk to Venice Beach & Downtown! Couple's Condo

Venice Island

A wooden staircase leading to a sandy beach with a clear view of the ocean and a partly cloudy sky.

A modern kitchen with a built-in island, stainless steel appliances, and wooden cabinets.

A wooden deck with outdoor furniture, including a table and chairs, surrounded by palm trees and greenery.

A narrow pathway flanked by wooden and white fences, leading to a building with a tiled roof.

12. Manasota Beach House

Manasota Key

A modern kitchen with white cabinets, granite countertops, and a built-in oven.

A spacious living room with a black leather sofa, a ceiling fan, and a dining area in the background.

A bedroom with a bed, nightstand, dresser, and ceiling fan.

A modern living room with a white sofa, a large abstract painting, and a wooden floor.

13. 3 Mi to Venice Beach: Pet-friendly Home w/ Yard

Venice Gardens

A living room with a ceiling fan, a flat-screen TV, a sofa, a coffee table, and a TV stand.

A backyard with a fire pit, wooden chairs, and a house in the background.

A bedroom with a bed, dresser, TV, and a door leading to another room.

A kitchen with a double sink, a microwave, and a window with a view of the outside.

14. < 1 Mi to Beach: Peaceful Escape in Nokomis

Nokomis

A covered outdoor area with white furniture, including chairs and a table, overlooking a beach.

A coastal hotel with multiple buildings, a beach, and ocean views.

An aerial view of a coastal area with a beach, buildings, and a clear view of the ocean.

A modern kitchen with white cabinetry, wooden shelves, and a stainless steel dishwasher.

15. Gulf View Condominiums

Manasota Key

$473

$1,079 total

includes taxes & fees

Oct 19 - Oct 20

A beach with clear turquoise water, a sandy shore, and tall grasses in the foreground.

A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

A living room with a sofa, a coffee table, and a dining area with chairs and a table.

A kitchen with a white countertop, stainless steel sink, and a ceiling fan. There is a dining area with wicker chairs and a table with a vase of flowers.

16. Pet-friendly Venice Vacation Rental, 3 Mi to Beach

South Venice

An aerial view of a coastal area with a beach, water, and a dense residential area with buildings.

A bedroom with a bed, a painting, a ceiling fan, and a bathroom visible through an open door.

A modern kitchen with stainless steel appliances, a dining area with a blue table, a living room with a beige sofa, and a ceiling fan.

A kitchen with a stainless steel sink, a window with blinds, and a framed picture on the wall.

17. Shoreline Bungalow

Nokomis

A compact living space with a dining area, kitchenette, and a ceiling fan.

A covered porch with a welcome mat, two chairs, a potted plant, and a small table.

A kitchen with white cabinets, a stove, and a sink.

18. 1 Mi to Nokomis Beach: Quiet Getaway w/ Fire Pit

Nokomis

A modern living room with a grey sofa set, a coffee table, and a ceiling fan.

A beach with clear blue sky, calm sea, and sparse vegetation.

A modern kitchen with stainless steel appliances, white cabinetry, and a blue-tiled backsplash.

19. Steps to Englewood Beach: Home w/ Outdoor Oasis!

Manasota Key

A house with a wooden deck, a sliding glass door, a ceiling fan, and a small rug.

A kitchen with wooden cabinets, stainless steel appliances, a large island, and a view of the living area.

A modern kitchen with a dining area, wooden flooring, and a TV displaying 'DEPP v HEARD'.

A tiki bar with a thatched roof, three wicker bar stools, and a dartboard on the wall.

20. Casa Azul - Games and Tiki Bar Vibes

South Venice

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Top neighborhoods in Osprey

An aerial view of a coastal area with a sandy beach, a road, and scattered buildings.

Sorrento Shores

Sorrento Shores delivers waterfront living at its most peaceful. Private docks line the Intracoastal Waterway where you can cast a line or launch your kayak right from your vacation rental. The neighborhood's wide streets and contemporary homes create a genuine slice of Florida suburban life without tourist crowds. Nearby Oscar Scherer State Park offers hiking trails while Nokomis Beach awaits just a short drive away. Getting around requires wheels since this residential haven has limited public transit options. The neighborhood has no restaurants or shops within its boundaries, so plan to venture 10-15 minutes to nearby Laurel or Sarasota for dining and groceries. The trade-off? Authentic waterfront tranquility that feels worlds away from Florida's busier destinations.

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A river with boats, a bridge, and a cityscape with tall buildings.

Bay Acres

Bay Acres offers a serene waterfront escape where travelers can enjoy the scenic beauty of Little Sarasota Bay. The quiet, tree-lined streets filled with upscale homes provide an authentic glimpse into Florida coastal living. Just minutes away, you'll find Historic Spanish Point, Oscar Scherer State Park, and the pristine shores of Siesta Key Beach. Getting around Bay Acres is best done by car, with ample parking throughout the residential community. Waterfront properties often feature private docks perfect for boating, fishing, or simply watching the spectacular sunsets. The peaceful atmosphere makes this neighborhood ideal for travelers seeking a relaxing retreat away from tourist crowds.

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Top landmarks in Osprey

A forest with tall trees and a dirt path.

Oscar Scherer State Park

8.8/10 (83 reviews)

Oscar Scherer State Park is 1.4 mi (2.3 km) from central Osprey, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?

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A white wooden chapel with a triangular roof, surrounded by trees.

Historic Spanish Point

9.0/10 (42 reviews)

If you're planning a bit of sightseeing during your trip, head to Historic Spanish Point— just one of the landmarks located 0.4 mi (0.7 km) from central Osprey. Why not take a stroll along the beaches and watch the sunset while you're here?

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Learn more about Osprey

Notable for its live music, Osprey features attractions such as Turtle Beach and Nokomis Beach. Visitors to this beachside city speak highly of the bars whereas sights include Oscar Scherer State Park and Jim Neville Marine Preserve.

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About the destination

Osprey is a friendly locale known for its restaurants and bars. Hunt for sand dollars at Turtle Beach and Nokomis Beach. Popular sights in the surrounding area include Siesta Key Beach.