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Osprey Holidays

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Where to stay in Osprey

Find the best Osprey areas for the activities you enjoy most. Learn more about Osprey
Learn more about Osprey
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Sorrento Shores

Sorrento Shores offers an authentic slice of upscale Florida waterfront living along the peaceful Intracoastal Waterway. This residential haven gives travellers a quiet retreat from tourist crowds while still being close to attractions. The area features contemporary and Mediterranean-style homes with private docks and boat access. Water activities define life here, with excellent opportunities for kayaking, fishing, and boating right from your doorstep. The tranquil streets and gentle water sounds create a perfect atmosphere for relaxation. Nearby Oscar Scherer State Park and Nokomis Beach provide natural beauty just a short drive away.

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

Bay Acres

Bay Acres offers a tranquil waterfront retreat along Little Sarasota Bay where upscale homes line quiet streets away from tourist crowds. Travellers can enjoy boating, fishing, or simply watching spectacular sunsets over calm waters. The peaceful residential atmosphere provides an authentic glimpse into Florida coastal living. This exclusive area features Mediterranean and contemporary architecture surrounded by manicured tropical landscapes and natural beauty. While shopping and dining options require a short drive to nearby Osprey or Sarasota, the trade-off is exceptional privacy and direct access to the bay's recreational opportunities.

Discover the most popular places to visit in Osprey

A forest with tall trees and a dirt path.
Photo by Frank Methling
Open Photo by Frank Methling

Oscar Scherer State Park

8.8/10 (83 reviews)
A sanctuary for endangered Florida scrub-jays, Oscar Scherer State Park offers trails through diverse ecosystems. Paddle South Creek or swim in Lake Osprey after spotting wildlife in the scrubby flatwoods.

What to do in Osprey

HydroCats - 2 Hour CraigCat Sightseeing Tour

HydroCats - 2 Hour CraigCat Sightseeing Tour

€115
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
See all activities in Osprey

Osprey Hotel Deals

Exterior

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
4.0 star property
2.8 km from Osprey
8.8 out of 10, Excellent, (1,234 reviews)
"The entire property was clean, quiet, and welcoming, making it easy to relax and enjoy my trip. I truly appreciated the outstanding customer service and attention to detail."
The price is €106
includes taxes & fees
6 Aug - 7 Aug
Casey Key Resorts - Mainland
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.
See all properties in Osprey

Frequently Asked Questions

How much does an Osprey holiday package cost?

Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Osprey costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Osprey?

August, September and November are great times to look for cheap Osprey holiday packages. Travelling in less busy periods means you can usually find lower prices on hotels and flights.

How many days is enough for Osprey?

Dedicate at least 3 days for your Osprey holiday to really immerse yourself in everything that makes this place special. Stroll around popular areas, including Laurel and Casey Key. Then make a beeline for major sights such as Oscar Scherer State Park and The Oaks Club. With a clever itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Osprey? Consider squeezing in a day trip or two.

Is it worth booking a holiday package to Osprey?

Osprey has everything you need for an amazing trip. Get your Osprey holiday off to a flying start by checking out major attractions like Oscar Scherer State Park.

How to find the best Osprey package deals?

Bagging a cheap Osprey package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can personalise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Osprey package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.

Is it cheaper to book an Osprey holiday as a package?

Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a customised Osprey holiday by choosing your favourite accommodation type, airline and car class.

When to book a holiday package to Osprey?

Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Osprey getaway.

How to plan a trip to Osprey?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Osprey.
  2. Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Osprey.
  3. Decide how long to go away for: Now that you're more familiar with Osprey, you can work out the ideal length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Osprey holiday package that brings all your bookings together.

Book with confidence

Things to do in and around Osprey

Osprey, Florida, is an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can enjoy a variety of activities, including golf at local courses, exploring recreational areas, and embarking on weekend getaways. The region offers exciting destinations and easy adventures, perfect for a Mediterranean-style escape or a theatrical break, ensuring a memorable holiday experience for all.

Shopping

For shopping in Osprey, visit Pelican Plaza, just 3.2km away, offering a lively mix of businesses and entertainment. Sarasota Square, located 4.8km away, is another great option with a family-friendly atmosphere. If you're up for a drive, explore the Siesta Key Farmers Market, 11.3km from Osprey.

Recreation

At Ed Smith Stadium, immerse yourself in the energetic atmosphere of live sports events just 17.7km from Osprey. Stoneybrook Golf & Country Club offers a serene outdoor golfing experience only 3.2km away, while The Oaks Club provides luxurious relaxation and exclusive amenities right in Osprey.

Adventure

Embark on the scenic Sarasota BayWalk, a delightful hiking trail 17.7km from Osprey, or challenge yourself at the Payne Park Tennis Center, located 16.1km away. For a unique experience, wander the Canopy Walkway and Boylston Nature Trail, a treetop walk 19.3km from Osprey.

Nightlife

In Osprey, Florida, enjoy a laid-back nightlife with charming bars and restaurants along the waterfront. Nearby Sarasota offers vibrant nightlife, featuring live music venues and trendy lounges. Explore the local craft beer scene or indulge in fine dining for a relaxed evening atmosphere.

Find the best attractions in and around Osprey

Osprey, Florida, is an ideal destination for beach and outdoor enthusiasts, offering a delightful family vacation experience. Visitors can explore a variety of attractions, including beautiful beaches, urban parks, and scenic jetties and piers. Whether you're seeking relaxation by the shore or engaging in outdoor activities, Osprey’s diverse points of interest cater to all types of travellers looking for memorable experiences in a charming coastal setting.

  • Siesta Key Beach: Experience the stunning beauty of Siesta Key Beach, renowned for its powdery white sand and crystal-clear waters. Located 9.7km from Osprey, this beach offers a relaxing atmosphere perfect for sunbathing, swimming, and water sports, all set against a backdrop of vibrant sunsets.
  • Historic Spanish Point: Immerse yourself in the rich history and culture of Florida at Historic Spanish Point, an archaeological site in Osprey. Explore ancient Native American sites, beautiful gardens, and historic structures that tell the story of the area's past.
  • Centennial Park: Enjoy family-friendly activities at Centennial Park, situated 11.3km from Osprey. This urban park features playgrounds, picnic areas, and walking paths, making it an ideal spot for outdoor relaxation and enjoying the vibrant city atmosphere.

Best time to go to Osprey

The best time to visit Osprey is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Tips to save on your trip to Osprey

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Osprey during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.